PubChem overview of oxalic acid properties

11/5/2015
oxalicacid|C2H2O4PubChem
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U.S.NationalLibraryofMedicine
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SearchCompounds
CHEMISTRY
D A T A B A S E
PUBCHEM COMPOUND OXALICACID
OxalicAcid
CitethisRecord
Vendors
Drug Information
Pharmacology
Literature
Patents
Bioactivities
PubChemCID:
971
OxalicacidEthanedioicacid144627AktisalAquisalOxiric
ChemicalNames:
acid More...
MolecularFormula:
C2H2O4
MolecularWeight:
90.03488g/mol
InChIKey:
MUBZPKHOEPUJKRUHFFFAOYSAN
UNII:
9E7R5L6H31
SafetySummary:
LaboratoryChemicalSafetySummary(LCSS)
ModifyDate:
20151031
CreateDate:
20040916
Oxalicacidisastrongdicarboxylicacidoccurringinmanyplantsandvegetables.Itisproducedinthebodyby
metabolismofglyoxylicacidorascorbicacid.Itisnotmetabolizedbutexcretedintheurine.Itisusedasan
analyticalreagentandgeneralreducingagent.
fromMeSH
Oxalicacidisanodorlesswhitesolid.Sinksandmixeswithwater.(USCG,1999)
PhysicalDescriptionfromCAMEOChemicals
http://pubchem.ncbi.nlm.nih.gov/compound/oxalic_acid#section=ChemicalandPhysicalProperties
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Contents
12DStructure
23DConformer
3NamesandIdentifiers
4ChemicalandPhysicalProperties
5RelatedRecords
6ChemicalVendors
7DrugandMedicationInformation
8PharmacologyandBiochemistry
9UseandManufacturing
10Identification
11SafetyandHazards
12Toxicity
13Literature
14Patents
15BiomolecularInteractionsandPathways
16BiologicalTestResults
17Classification
18InformationSources
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1 2DStructure
Search
Download
GetImage
Magnify
fromPubChem
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2 3DConformer
Search
Download
GetImage
ShowHydrogens
ShowAtoms
Magnify
Animate
fromPubChem
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3 NamesandIdentifiers
3.1 ComputedDescriptors
3.1.1 IUPACName
oxalicacid
fromPubChem
3.1.2 InChI
InChI=1S/C2H2O4/c31(4)2(5)6/h(H,3,4)(H,5,6)
fromPubChem
3.1.3 InChIKey
MUBZPKHOEPUJKRUHFFFAOYSAN
fromPubChem
3.1.4 CanonicalSMILES
C(=O)(C(=O)O)O
fromPubChem
3.2 OtherIdentifiers
3.2.1 CAS
144627
fromDrugBank,EPAChemicalDataReport,ILOICSC,NIOSHPocketGuide,OSHAOccupationalChem
3.2.2 ECNumber
2056343
fromILOICSC
2056343
fromECHA
2089321
fromECHA
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2139508
fromECHA
3.2.3 ICSCNumber
0529
fromILOICSC
3.2.4 RTECSNumber
RO2450000
fromILOICSC
RO2450000
fromNIOSHPocketGuide
3.2.5 UNNumber
3261
fromILOICSC,CAMEOChemicals
1759
fromNJDOHRTKHazardousSubstanceList
3.2.6 UNII
9E7R5L6H31
fromFDA/SPLIndexingdata
3.2.7 Wikipedia
Oxalicacid
fromWiki
3.3 Synonyms
3.3.1 MeSHSynonyms
1. Acid,Oxalic
11. FerricOxalate
21. MonosodiumOxalate
31. Oxalate,
2. AluminumOxalate
12. Iron(2+)Oxalate(1:1)
22. Oxalate,Aluminum
32. Oxalate,
3. AmmoniumOxalate
13. Iron(3+)Oxalate
23. Oxalate,Chromium
33. Oxalate,
4. Chromium(2+)Oxalate
14. IronOxalate
24. Oxalate,Diammonium
34. Oxalate,
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5. Chromium(3+)Oxalate(3:2)
15. MagnesiumOxalate
25. Oxalate,Dilithium
35. Oxalate,
6. ChromiumOxalate
16. MagnesiumOxalate(1:1)
26. Oxalate,Dipotassium
36. Oxalate,
7. DiammoniumOxalate
17. Manganese(2+)Oxalate(1:1)
27. Oxalate,Disodium
37. Oxalate,
8. DilithiumOxalate
18. MonoammoniumOxalate
28. Oxalate,Ferric
38. OxalicA
9. DipotassiumOxalate
19. MonohydrogenMonopotassiumOxalate
29. Oxalate,Iron
39. Potassiu
20. MonopotassiumOxalate
30. Oxalate,Magnesium
40. Potassiu
10. DisodiumOxalate
fromMeSH
3.3.2 DepositorSuppliedSynonyms
1. oxalicacid
11. Acidumoxalicum
21. Acidoossalico[Italian]
31. CHEBI:16995
2. ethanedioicacid
12. Acideoxalique
22. Kyselinastavelova[Czech]
32. MUBZPKHOEPUJ
3. 144627
13. Acidoossalico
23. EPAPesticideChemicalCode009601
33. EINECS2056343
4. Aktisal
14. CaswellNo.625
24. HOOCCOOH
34. STK379550
5. Aquisal
15. Ethanedionicacid
25. CCRIS1454
35. Oxalicacid
6. Oxiricacid
16. Oxaalzuur[Dutch]
26. AI326463
36. DSSTox_CID_581
7. oxalate
17. NCIC55209
27. HSDB1100
37. C00209
8. Oxaalzuur
18. Oxalsaeure[German]
28. NSC62774
38. DSSTox_RID_779
9. Oxalsaeure
19. Acideoxalique[French]
29. BRN0385686
39. DSSTox_GSID_25
20. Ethane1,2dioicacid
30. UNII9E7R5L6H31
40. Oxalicacidstanda
10. Kyselinastavelova
fromPubChem
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4 ChemicalandPhysicalProperties
4.1 ComputedProperties
MolecularWeight
90.03488g/mol
MolecularFormula
C2H2O4
XLogP3
0.3
HydrogenBondDonorCount
HydrogenBondAcceptorCount
RotatableBondCount
ExactMass
89.995309g/mol
MonoisotopicMass
89.995309g/mol
TopologicalPolarSurfaceArea
74.6A^2
HeavyAtomCount
FormalCharge
Complexity
71.5
IsotopeAtomCount
DefinedAtomStereocenterCount
UndefinedAtomStereocenterCount
DefinedBondStereocenterCount
UndefinedBondStereocenterCount
CovalentlyBondedUnitCount
1
fromPubChem
4.2 ExperimentalProperties
4.2.1 PhysicalDescription
1. DryPowder
2. OtherSolid
3. PelletsLargeCrystals
fromEPAChemicalDataReport
HYGROSCOPICCOLOURLESSCRYSTALSORWHITEPOWDER.
fromILOICSC
Colorless,odorlesspowderorgranularsolid.
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fromNIOSHPocketGuide,OSHAOccupationalChemicalDB
Oxalicacidisanodorlesswhitesolid.Sinksandmixeswithwater.(USCG,1999)
fromCAMEOChemicals
4.2.2 Color
ANHYDROUSOXALICACID,CRYSTALLIZEDFROMGLACIALACETICACIDISORTHORHOMBIC,
CRYSTALSBEINGPYRAMIDALORELONGATEDOCTAHEDRA
Budavari,S.(ed.).TheMerckIndexEncyclopediaofChemicals,DrugsandBiologicals.Rahway,NJ:MerckandCo.,Inc.,
1989.,p.1093
fromHSDB
Colorlesspowderorgranularsolid[Note:Theanhydrousform(COOH)2isawhitepowder].
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.94116.Washington,D.C.:U.S.
GovernmentPrintingOffice,June1994.,p.238
fromHSDB
4.2.3 Odor
Odorless.
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.94116.Washington,D.C.:U.S.
GovernmentPrintingOffice,June1994.,p.238
fromHSDB
4.2.4 BoilingPoint
Sublimes
4.2.5 MeltingPoint
189.5DEGC(DECOMPOSES)
1989.,p.1093
fromHSDB
189.5decC
PhysProp
fromDrugBank
189.5C
fromILOICSC
215F
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372F(Decomposes)
(NTP,1992)
fromCAMEOChemicals
4.2.6 Solubility
100GAQSOLNSATURATED@15DEGCCONTAINS6.71G100GAQSOLNSATURATED@20DEGC
CONTAINS8.34G100GAQSOLNSATURATED@25DEGCCONTAINS9.81G
1989.,p.1093
fromHSDB
VERYSOLINETHANOLSLIGHTLYSOLINETHERINSOLINBENZENE,CHLOROFORM,PETROLEUM
ETHER
Weast,R.C.(ed.).HandbookofChemistryandPhysics.60thed.BocaRaton,Florida:CRCPressInc.,1979.,p.C409
fromHSDB
Watersolubilityof220,000mg/lat25degC
YalkowskySHetalArizonaDataBaseofWaterSolubility(1989)
fromHSDB
WaterSolubility
220000mg/L(at25C)
YALKOWSKY,SH&DANNENFELSER,RM(1992)
fromDrugBank
Solubilityinwater,g/100mlat20C:910(moderate)
fromILOICSC
14%[g/100mL]
50to100mg/mLat75F
(NTP,1992)
fromCAMEOChemicals
4.2.7 Density
1.90@17DEG/4DEGC,ALPHA
1989.,p.693
fromHSDB
Density(atC):1.9g/cm
fromILOICSC
1.9
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1.9at59F
(USCG,1999)
fromCAMEOChemicals
4.2.8 VaporDensity
4.3
(NTP,1992)
fromCAMEOChemicals
4.2.9 VaporPressure
0.54mm@105degC
Clayton,G.D.andF.E.Clayton(eds.).Patty'sIndustrialHygieneandToxicology:Volume2A,2B,2C:Toxicology.3rded.New
York:JohnWileySons,19811982.,p.4936
fromHSDB
<0.001mmHg
<0.001
fromOSHAOccupationalChemicalDB
0.001mmHgat68F
(NTP,1992)
fromCAMEOChemicals
4.2.10 LogP
0.81
fromILOICSC
4.2.11 LogS
0.38
ADMEResearch,USCD
fromDrugBank
4.2.12 Stability
OXALICACIDCANBEDEHYDRATEDBYCAREFULDRYING@100DEGC,BUTLOSSESOCCUR
THROUGHSUBLIMATION/OXALICACIDDIHYDRATE/
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1989.,p.897
fromHSDB
4.2.13 Decomposition
...DECOMPPRODUCTSINCLCARBONMONOXIDE&FORMICACID.
NationalFireProtectionAssociation.FireProtectionGuideonHazardousMaterials.7thed.Boston,Mass.:NationalFire
ProtectionAssociation,1978.,p.49224
fromHSDB
seeNotes.
fromILOICSC
4.2.14 HeatofCombustion
245.61KJ/mol
KirkOthmerEncyclopediaofChemicalTechnology.3rded.,Volumes126.NewYork,NY:JohnWileyandSons,19781984.,p.
V16619(1981)
fromHSDB
4.2.15 DissociationConstants
pKa1:1.46pKa2:4.40
Clayton,G.D.andF.E.Clayton(eds.).Patty'sIndustrialHygieneandToxicology:Volume2A,2B,2C:Toxicology.3rded.New
York:JohnWileySons,19811982.,p.4936
fromHSDB
4.2.16 KovatsRetentionIndex
Semistandardnonpolar
748
fromNIST
4.3 CrystalStructures
CrystalStructures:1of5
CCDCNumber
929767
CrystalStructureData
DOI:10.5517/cc106hh6
AssociatedArticle
DOI:10.1021/cg400668w
fromTheCambridgeStructuralDatabase
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CCDCNumber
929768
DOI:10.5517/cc106hj7
AssociatedArticle
DOI:10.1021/cg400668w
CCDCNumber
929769
DOI:10.5517/cc106hk8
AssociatedArticle
DOI:10.1021/cg400668w
CCDCNumber
929770
DOI:10.5517/cc106hl9
AssociatedArticle
DOI:10.1021/cg400668w
CCDCNumber
929771
DOI:10.5517/cc106hmb
AssociatedArticle
DOI:10.1021/cg400668w
4.4 SpectralProperties
IR:8279(SadtlerResearchLaboratoriesIRGratingCollection)
Weast,R.C.andM.J.Astle.CRCHandbookofDataonOrganicCompounds.VolumesIandII.BocaRaton,FL:CRCPressInc.
1985.,p.V1946
fromHSDB
NMR:17060(SadtlerResearchLaboratoriesSpectralCollection)
1985.,p.V1946
fromHSDB
MASS:52(NationalBureauofStandardsEPANIHMassSpectraDataBase,NSRDSNBS63)
1985.,p.V1946
fromHSDB
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4.4.1 GCMS
1of3
NISTNumber
229396
Library
Mainlibrary
TotalPeaks
20
m/zTopPeak
45
m/z2ndHighest
46
m/z3rdHighest
29
CLICKTOLOAD...
Thumbnail
fromNIST
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5 RelatedRecords
CLICKTOLOAD...
fromNCBI
5.1 RelatedCompoundswithAnnotation
CLICKTOLOAD...
fromPubChem
5.2 RelatedCompounds
SameConnectivity
7records
SameParent,Connectivity
930records
SameParent,Exact
920records
Mixtures,Components,and
NeutralizedForms
37111records
SimilarCompounds
279records
SimilarConformers
396records
fromPubChem
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5.3 Substances
5.3.1 RelatedSubstances
All
139987records
Same
391records
Mixture
139596records
fromPubChem
5.3.2 SubstancesbyCategory
CLICKTOLOAD...
fromPubChem
5.4 EntrezCrosslinks
PubMed
3531records
ProteinStructures
77records
Taxonomy
2records
Gene
11records
fromPubChem
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6 ChemicalVendors
CLICKTOLOAD...
fromPubChem
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7 DrugandMedicationInformation
7.1 DrugWarning
Ascorbicacidingestioninhighdosesisassociatedwithoxalatedepositionintissueindialysispatients./Oxalates/
Haddad,L.M.,ClinicalManagementofPoisoningandDrugOverdose.2nded.Philadelphia,PA:W.B.SaundersCo.,1990.,p.
702
fromHSDB
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8 PharmacologyandBiochemistry
8.1 MeSHPharmacologicalClassification
ReducingAgents
Materialsthataddanelectrontoanelementorcompound,thatis,decreasethepositivenessofitsvalence.(From
McGrawHillDictionaryofScientificandTechnicalTerms,5thed) SeealistofPubChemcompoundsmatching
thiscategory.
fromMeSH
8.2 Absorption,DistributionandExcretion
TARTARIC&OXALICACIDSAREEXCRETEDINURINEUNCHANGED.
Parke,D.V.TheBiochemistryofForeignCompounds.Oxford:PergamonPress,1968.,p.141
fromHSDB
Theabsorptionof(14)ClabelledoxalicacidwasstudiedinWistarrats,CD1miceandNMRImice.Oxalicacidin
solutionwasgiventotheanimalsbygavageeitherwithwateraloneorwith0.625g/kgbodywtofxylitol.Both
xylitoladaptedanimalsandanimalsnotpreviouslyexposedtoxylitolwereused.Adaptationtoxylitoldiets
enhancedtheabsorptionandurinaryexcretionofthelabel(oxalicacid)inbothstrainsofmicebutnotinrats.
Earlierstudieshaveindicatedahighincidenceofbladdercalculiinmicebutnotinratsfedhighamountsofxylitol.
Theresultsofthepresentstudyofferonelikelyexplanationfortheincreasedformationofbladdercalculiasaresult
ofoversaturationofurinewithoxalate. Abstract:PubMed
SalminenSetalToxicolLett44(12):11320(1988)
fromHSDB
8.3 Metabolism/Metabolites
INRABBIT,MAJORENDPRODUCTOFMETABOF(14)CETHYLENEGLYCOLISRESPCARBONDIOXIDE
(60%OFDOSEIN3DAYS),&METABOLITESEXCRETEDINURINEAREUNCHANGEDETHYLENE
GLYCOL(10%)&OXALICACID(0.1%)....GLYCOLALDEHYDE,GLYCOLLICACID&GLYOXYLICACIDARE
INTERMEDIATESINCONVERSIONTOCARBONDIOXIDE.
fromHSDB
INOXIDATIVEMETABOFETHYLENEGLYCOLINMAMMALS,SPECIESVARIATIONSOCCURWHICH
EXPLAIN...DIFFERENCESINTOXICITY.GLYCOLISOXIDIZEDBYMAJORPATHWAYINTOCARBON
DIOXIDE,&BYMINORPATHWAYTO...OXALICACID.EXTENTOFFORMATIONOFOXALICACIDIS
DEPENDENTONDOSELEVEL,BUTHAS...BEENSHOWNTOVARYWITHSPECIES...
fromHSDB
INITIALSTEPSINOXIDATIONOFETHYLENEGLYCOLTODIALDEHYDE(GLYOXAL)&TOGLYOXYLIC
ACIDSEEMTOBEMEDIATEDBYALCDEHYDROGENASEDECARBOXYLATIONOFGLYOXYLICACID
YIELDSCARBONDIOXIDE&FORMICACID.GLYOXYLICACIDISALSOOXIDIZEDTOOXALICACID.
Gilman,A.G.,L.S.Goodman,andA.Gilman.(eds.).GoodmanandGilman'sThePharmacologicalBasisofTherapeutics.7thed.
NewYork:MacmillanPublishingCo.,Inc.,1985.,p.1637
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fromHSDB
Piridoxilateisanassociationofglyoxylicacidandpyridoxineinwhichpyridoxineissupposedtofacilitateinvivo
transformationofglyoxylicacidtoglycineratherthantooxalicacid.However,ithasrecentlybeenshownthatlong
termtreatmentwithpiridoxilatemayresultinoverproductionofoxalicacidandincalciumoxalatenephrolithiasis.A
patientinwhompiridoxilateinducedbothoxalatenephrolithiasisandchronicoxalatenephropathywithrenal
insufficiency,anassociationthathasnotbeenpreviouslydescribed,wasreported.Therefore,piridoxilateshouldbe
addedtothelistofchemicalsresponsibleforchronicoxalatenephropathy. Abstract:PubMed
VigeralPetalNephrolDialTransplant2(4):2758(1987)
fromHSDB
CyclosporinAinterfereswithoxalatemetabolismand,therefore,shouldbegivenwithutmostcautioninpatients
withprimaryhyperoxaluria. Abstract:PubMed
DrachmanRetalChildNephrolUrol9(12):902(1988)
fromHSDB
8.4 MechanismofAction
Metabolicallyitstoxicityisbelievedduetothecapacityofoxalicacidtoimmobilizecalciumandthusupsetthe
calciumpotassiumratioincriticaltissues.
AmericanConferenceofGovernmentalIndustrialHygienists.DocumentationoftheThresholdLimitValuesandBiological
ExposureIndices.5thed.Cincinnati,OH:AmericanConferenceofGovernmentalIndustrialHygienists,1986.,p.451
fromHSDB
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9 UseandManufacturing
9.1 Uses
9.1.1 IndustryUses
1. Paintadditivesandcoatingadditivesnotdescribedbyothercategories
2. Photosensitivechemicals
3. Surfaceactiveagents
9.1.2 ConsumerUses
1. CleaningandFurnishingCareProducts
2. LaundryandDishwashingProducts
3. PaintsandCoatings
4. PhotographicSupplies,Film,andPhotochemicals
9.2 MethodsofManufacturing
MADEBYPASSINGCARBONMONOXIDEINTOCONCENTRATEDSODIUMHYDROXIDEORBYHEATING
SODIUMFORMATEINPRESENCEOFSODIUMHYDROXIDEORSODIUMCARBONATE.
1989.,p.1093
fromHSDB
OXALICACIDISPRODUCEDCOMMERCIALLYBYNITRICACIDOXIDATIONOFSTARCH,SUGAR,OR
ETHYLENEGLYCOL
CHEMICALPRODUCTSSYNOPSIS:OXALICACID,1984
fromHSDB
OXALICACIDISACOPRODUCTOFTHEFERMENTATIONOFMOLASSESTOCITRICACID.OXALICACID
CANBEMADEBYFUSINGSAWDUST(OROTHERFORMSOFCELLULOSE)WITHAMIXTUREOF
SODIUMHYDROXIDEANDPOTASSIUMHYDROXIDE.TEXACOWASGRANTEDAPATENTIN1973FOR
THEELECTROLYTICSYNTHESISOFOXALICACIDFROMCARBONDIOXIDEANDHYDROGEN.
fromHSDB
9.3 Formulations/Preparations
Technical(crystalsandpowder)chemicallypure:agradedesignationsignifyingaminimumofimpurities,butnot
100%purity.
Sax,N.I.andR.J.Lewis,Sr.(eds.).Hawley'sCondensedChemicalDictionary.11thed.NewYork:VanNostrandReinholdCo.,
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1987.,p.862
fromHSDB
THECOMMERCIALPRODUCTISCOMPRISEDOFWHITETOCOLORLESSMONOCLINICPRISMSOR
GRANULESCONTAINING71.42wt%ANHYDROUSOXALICACIDAND28.58wt%WATER
KirkOthmerEncyclopediaofChemicalTechnology.3rded.,Volumes126.NewYork,NY:JohnWileyandSons,19781984.,p.
V16618(1981)
fromHSDB
9.4 Consumption
27%FORTEXTILEFINISHING,STRIPPINGANDCLEANING27%FORMETALANDEQUIPMENT
CLEANING25%ASACHEMICALINTERMEDIATE2%FORLEATHERTANNING19%FORMISC
APPLICATIONS(1971)
SRI
fromHSDB
33%FORTEXTILE/APPLICATIONS/20%FORMETAL7%FORLEATHER20%FOROXALATESAND20%
FOROTHERUSE(1983)
fromHSDB
9.5 U.S.Production
(1972)1.0X10+10G
SRI
fromHSDB
(1974)8.17X10+9G
SRI
fromHSDB
(1982)9.08X10+8G(EST)
fromHSDB
9.6 U.S.Imports
(1972)8.6X10+8G
SRI
fromHSDB
(1975)1.73X10+9G
SRI
fromHSDB
(1984)9.31X10+9g
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BUREAUOFTHECENSUS.U.S.IMPORTSFORCONSUMPTIONANDGENERALIMPORTS1984p.1357
fromHSDB
9.7 U.S.Exports
(1972)NEGLIGIBLE
SRI
fromHSDB
1.68X10+8g
BUREAUOFTHECENSUS.U.S.EXPORTS,SCHEDULEE,1984p.279
fromHSDB
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10 Identification
10.1 AnalyticLaboratoryMethods
VEGETABLEPRODUCTS:TITRATIONORATOMICABSORPTIONSPECTROPHOTOMETRY.
AssociationofOfficialAnalyticalChemists.OfficialMethodsofAnalysis.15thed.andSupplements.Washington,DC:
AssociationofAnalyticalChemists,1990,p.15/994974.24
fromHSDB
AIRSAMPLE.PROCEDURE:TITRATION.
Sunshine,I.(ed.).CRCHandbookofAnalyticalToxicology.Cleveland:TheChemicalRubberCo.,1969.,p.649
fromHSDB
10.2 ClinicalLaboratoryMethods
APPLICATION:SERUMORURINE.METHOD:FLUORESCENCEANALYSIS.
Sunshine,I.(ed.).CRCHandbookofAnalyticalToxicology.Cleveland:TheChemicalRubberCo.,1969.,p.927
fromHSDB
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11 SafetyandHazards
11.1 HazardsIdentification
11.1.1 GHSClassification
Signal:Danger
Harmfulifswallowed
Causessevereskinburnsandeyedamage
Maycauserespiratoryirritation
fromILOICSC
Signal:Wng
H312Harmfulincontactwithskin
H302Harmfulifswallowed
fromREGULATION(EC)No1272/2008
11.1.2 CLPHazardClassandCategoryCodes
CLPHazardClasssandCategoryCodes
AcuteTox.4*
AcuteTox.4*
fromREGULATION(EC)No1272/2008
11.1.3 HealthHazard
Asdustorasasolution,cancausesevereburnsofeyes,skin,ormucousmembranes.Ingestionof5gramshas
causeddeathwithsymptomsofnausea,shock,collapse,andconvulsionscomingonrapidly.Repeatedor
prolongedskinexposurecancausedermatitisandslowhealingulcers.(USCG,1999)
fromCAMEOChemicals
Corrosive
fromNJDOHRTKHazardousSubstanceList
11.1.4 FireHazard
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Combustible.Givesoffirritatingortoxicfumes(orgases)inafire.
fromILOICSC
11.1.5 SkinHazard
Redness.Pain.Skinburns.
fromILOICSC
11.1.6 InhalationHazard
Cough.Sorethroat.Burningsensation.Shortnessofbreath.Labouredbreathing.Headache.
fromILOICSC
11.1.7 EyeHazard
Redness.Pain.Blurredvision.Burns.
fromILOICSC
11.1.8 IngestionHazard
Sorethroat.Burningsensation.Abdominalpain.Labouredbreathing.Convulsions.Paralysis.Cardiacdysrhythmia.
Shockorcollapse.
fromILOICSC
11.1.9 Skin,Eye,andRespiratoryIrritations
Thechiefeffectsofinhalationofthedustorvaporareirritationoftheeyesandupperrespiratorytract.
Sax,N.I.DangerousPropertiesofIndustrialMaterials.6thed.NewYork,NY:VanNostrandReinhold,1984.,p.2098
fromHSDB
11.2 SafetyandHazardProperties
11.2.1 Flammability
CombustibleSolid
11.2.2 NFPAHazardClassification
Health:3.3=Materialsthat,onshortexposure,couldcauseserioustemporaryorresidualinjury,includingthose
requiringprotectionfromallbodilycontact.Firefightersmayentertheareaonlyiftheyareprotectedfromall
contactwiththematerial.Fullprotectiveclothing,includingselfcontainedbreathingapparatus,coat,pants,gloves,
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boots,andbandsaroundlegs,arms,andwaist,shouldbeprovided.Noskinsurfaceshouldbeexposed.
FireProtectionGuidetoHazardousMaterials.12ed.Quincy,MA:NationalFireProtectionAssociation,1997.,p.4999
fromHSDB
Flammability:1.1=Thisdegreeincludesmaterialsthatmustbepreheatedbeforeignitionwilloccur,suchasClass
IIIBcombustibleliquidsandsolidsandsemisolidswhoseflashpointexceeds200degF(93.4degC),aswellas
mostordinarycombustiblematerials.Watermaycausefrothingifitsinksbelowthesurfaceoftheburningliquid
andturnstosteam.However,awaterfogthatisgentlyappliedtothesurfaceoftheliquidwillcausefrothingthat
willextinguishthefire.
fromHSDB
Reactivity:0.0=Thisdegreeincludesmaterialsthatarenormallystable,evenunderfireexposureconditions,and
thatdonotreactwithwater.Normalfirefightingproceduresmaybeused.
fromHSDB
11.2.3 NFPAFireRating
1
fromOSHAOccupationalChemicalDB,CAMEOChemicals
11.2.4 NFPAReactivityRating
0
11.2.5 NFPAHealthRating
2
3
fromCAMEOChemicals
11.2.6 PhysicalDanger
Nodata.
fromILOICSC
11.2.7 ChemicalDanger
500mg/cum
NIOSH.NIOSHPocketGuidetoChemicalHazards.DHHS(NIOSH)PublicationNo.97140.Washington,D.C.U.S.Government
PrintingOffice,1997.,p.239
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fromHSDB
Decomposesoncontactwithhotsurfacesorflames.Thisproducesformicacidandcarbonmonoxide.Thesolution
inwaterisamediumstrongacid.Reactsviolentlywithstrongoxidants.Thisgeneratesfireandexplosionhazard.
Reactswithsomesilvercompounds.Thisproducesexplosivesilveroxalate.Attackssomeformsofplastic.
fromILOICSC
11.2.8 OSHAStandards
PermissibleExposureLimit:TableZ18hrTimeWeightedAvg:1mg/cum.
29CFR1910.1000(7/1/98)
fromHSDB
Vacated1989OSHAPELTWA1mg/cumSTEL2mg/cumisstillenforcedinsomestates.
fromHSDB
11.2.9 NIOSHRecommendations
RecommendedExposureLimit:10HrTimeWeightedAvg:1mg/cum.
fromHSDB
RecommendedExposureLimit:15MinShortTermExposureLimit:2mg/cum.
fromHSDB
11.3 FirstAidMeasures
11.3.1 FirstAid
Eye:Irrigateimmediately
Skin:Waterflushpromptly
Breathing:Respiratorysupport
Swallow:Medicalattentionimmediately Moreinformation...
EYES:Firstcheckthevictimforcontactlensesandremoveifpresent.Flushvictim'seyeswithwaterornormal
salinesolutionfor20to30minuteswhilesimultaneouslycallingahospitalorpoisoncontrolcenter.Donotputany
ointments,oils,ormedicationinthevictim'seyeswithoutspecificinstructionsfromaphysician.IMMEDIATELY
transportthevictimafterflushingeyestoahospitalevenifnosymptoms(suchasrednessorirritation)develop.
SKIN:IMMEDIATELYfloodaffectedskinwithwaterwhileremovingandisolatingallcontaminatedclothing.Gently
washallaffectedskinareasthoroughlywithsoapandwater.IMMEDIATELYcallahospitalorpoisoncontrolcenter
evenifnosymptoms(suchasrednessorirritation)develop.IMMEDIATELYtransportthevictimtoahospitalfor
treatmentafterwashingtheaffectedareas.INHALATION:IMMEDIATELYleavethecontaminatedareatakedeep
breathsoffreshair.Ifsymptoms(suchaswheezing,coughing,shortnessofBreathing,orburninginthemouth,
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throat,orchest)develop,callaphysicianandbepreparedtotransportthevictimtoahospital.Provideproper
respiratoryprotectiontorescuersenteringanunknownatmosphere.Wheneverpossible,SelfContainedBreathing
Apparatus(SCBA)shouldbeusedifnotavailable,usealevelofprotectiongreaterthanorequaltothatadvised
underProtectiveClothing.INGESTION:DONOTINDUCEVOMITING.Corrosivechemicalswilldestroythe
membranesofthemouth,throat,andesophagusand,inaddition,haveahighriskofbeingaspiratedintothe
victim'slungsduringvomitingwhichincreasesthemedicalproblems.Ifthevictimisconsciousandnotconvulsing,
give1or2glassesofwatertodilutethechemicalandIMMEDIATELYcallahospitalorpoisoncontrolcenter.
IMMEDIATELYtransportthevictimtoahospital.Ifthevictimisconvulsingorunconscious,donotgiveanythingby
mouth,ensurethatthevictim'sairwayisopenandlaythevictimonhis/hersidewiththeHeadachelowerthanthe
body.DONOTINDUCEVOMITING.TransportthevictimIMMEDIATELYtoahospital.(NTP,1992)
11.3.2 FireFirstAid
Usewaterspray,powder,foam,carbondioxide.
fromILOICSC
11.3.3 ExplosionFirstAid
Incaseoffire:keepdrums,etc.,coolbysprayingwithwater.
fromILOICSC
11.3.4 InhalationFirstAid
Freshair,rest.Halfuprightposition.Referimmediatelyformedicalattention.
fromILOICSC
11.3.5 SkinFirstAid
Removecontaminatedclothes.Rinseskinwithplentyofwaterorshowerforatleast15minutes.Referformedical
attention.
fromILOICSC
11.3.6 EyeFirstAid
Rinsewithplentyofwater(removecontactlensesifeasilypossible).Referimmediatelyformedicalattention.
fromILOICSC
11.3.7 IngestionFirstAid
Rinsemouth.DoNOTinducevomiting.Referimmediatelyformedicalattention.
fromILOICSC
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11.4 FireFightingMeasures
USEWATERSPRAY,DRYCHEM,"ALCRESISTANT"FOAM,ORCARBONDIOXIDE.DUSTMAYBE
REDUCEDWITHWATERSPRAY.AQUEOUSSOLUTIONMUSTBECONTAINEDFORDISPOSAL.USE
WATERTOKEEPFIREEXPOSEDCONTAINERSCOOL.WATERMAYCAUSEFOAMINGOFMOLTEN
MATERIAL./OXALICACIDDIHYDRATE/
fromHSDB
11.4.1 FireFighting
Firesinvolvingthiscompoundmaybecontrolledwithadrychemical,carbondioxideorHalonextinguisher.(NTP,
1992)
11.5 AccidentalReleaseMeasures
11.5.1 SpillageDisposal
Personalprotection:particulatefilterrespiratoradaptedtotheairborneconcentrationofthesubstance,protective
glovesandsafetygoggles.Sweepspilledsubstanceintocoveredplasticcontainers.Ifappropriate,moistenfirstto
preventdusting.Washawayremainderwithplentyofwater.
fromILOICSC
11.5.2 CleanupMethods
Coverwithsodaashorsodiumbicarbonate.Mixandaddwater.Neutralizeanddrainintoadrainwithsufficient
water.
ITII.ToxicandHazardousIndustrialChemicalsSafetyManual.Tokyo,Japan:TheInternationalTechnicalInformationInstitute,
1988.,p.389
fromHSDB
11.5.3 DisposalMethods
Oxalicacidisawastechemicalstreamconstituentwhichmaybesubjectedtoultimatedisposalbycontrolled
incineration.Pretreatmentinvolveschemicalreactionwithlimestoneorcalciumoxideformingcalciumoxalate.This
maythenbeincineratedutilizingparticulatecollectionequipmenttocollectcalciumoxideforrecycling.
USEPAEngineeringHandbookforHazardousWasteIncinerationp.218(1981)EPA68033025
fromHSDB
11.5.4 OtherPreventativeMeasures
Adequateventilation.
1988.,p.389
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fromHSDB
Theworkershouldimmediatelywashtheskinwhenitbecomescontaminated.
fromHSDB
Workclothingthatbecomeswetorsignificantlycontaminatedshouldberemovedandreplaced.
fromHSDB
Workerswhoseclothingmayhavebecomecontaminatedshouldchangeintouncontaminatedclothingbefore
leavingtheworkpremises.
fromHSDB
SRP:Contaminatedprotectiveclothingshouldbesegregatedinsuchamannersothatthereisnodirectpersonal
contactbypersonnelwhohandle,dispose,orcleantheclothing.Qualityassurancetoascertainthecompletenessof
thecleaningproceduresshouldbeimplementedbeforethedecontaminatedprotectiveclothingisreturnedforreuse
bytheworkers.Contaminatedclothingshouldnotbetakenhomeatendofshift,butshouldremainatemployee's
placeofworkforcleaning.
fromHSDB
SRP:Thescientificliteraturefortheuseofcontactlensesinindustryisconflicting.Thebenefitordetrimental
effectsofwearingcontactlensesdependnotonlyuponthesubstance,butalsoonfactorsincludingtheformofthe
substance,characteristicsanddurationoftheexposure,theusesofothereyeprotectionequipment,andthe
hygieneofthelenses.However,theremaybeindividualsubstanceswhoseirritatingorcorrosivepropertiesaresuch
thatthewearingofcontactlenseswouldbeharmfultotheeye.Inthosespecificcases,contactlensesshouldnot
beworn.Inanyevent,theusualeyeprotectionequipmentshouldbewornevenwhencontactlensesareinplace.
fromHSDB
11.6 HandlingandStorage
11.6.1 NonfireSpillResponse
NeutralizingAgentsforAcidsandCaustics:Limeorsodaash(USCG,1999)
11.6.2 SafeStorage
Separatedfromstrongoxidantsandfoodandfeedstuffs.Dry.Wellclosed.
fromILOICSC
11.6.3 StorageConditions
STOREINCOOL,DRY,WELLVENTILATEDLOCATION./OXALICACIDDIHYDRATE/
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Reynolds,J.E.F.,Prasad,A.B.(eds.)MartindaleTheExtraPharmacopoeia.28thed.London:ThePharmaceuticalPress,1982.,
p.49131
fromHSDB
11.7 ExposureControlandPersonalProtection
11.7.1 REL
TWA1mg/m3ST2mg/m3
11.7.2 PEL
TWA1mg/m3
11.7.3 PELTWA
1mg/m3
11.7.4 RELTWA
1mg/m3
11.7.5 RELSTEL
2mg/m3
11.7.6 IDLH
500mg/m3
11.7.7 ThresholdLimitValues
8hrTimeWeightedAvg(TWA):1mg/cum15minShortTermExposureLimit(STEL):2mg/cum.
AmericanConferenceofGovernmentalIndustrialHygienistsTLVsandBEIs.ThresholdLimitValuesforChemicalSubstances
andPhysicalAgentsandBiologicalExposureIndices.Cincinnati,OH,2008,p.45
fromHSDB
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11.7.8 OccupationalExposureLimits
TLV:1mg/masTWA(ACGIH2009).
EUOEL(selected):1mg/masTWA.
fromILOICSC
11.7.9 InhalationRisk
Evaporationat20Cisnegligibleaharmfulconcentrationofairborneparticlescan,however,bereachedquickly
whendispersed.
fromILOICSC
11.7.10 EffectsofShortTermExposure
Thesubstanceiscorrosivetotheeyes,skinandrespiratorytract.Corrosiveoningestion.Thesubstancemaycause
effectsonthecalciumbalanceafteringestion.Exposureathighlevelscouldcausedeath.
fromILOICSC
11.7.11 EffectsofLongTermExposure
Repeatedorprolongedcontactwithskinmaycausedermatitis.Exposuremayresultinkidneystones,slowhealing
ulcersandblackfingernails.
fromILOICSC
11.7.12 AllowableTolerances
Residuesofoxalicacidareexemptedfromtherequirementofatolerancewhenusedasacalciumchelatinghard
waterinhibitorinaccordancewithgoodagriculturalpracticesasinert(oroccasionallyactive)ingredientsinpesticide
formulationsappliedtogrowingcropsortorawagriculturalcommoditiesafterharvest.Limits:Nomoreoxalicacid
shouldbeusedthanisnecessarytochelatecalciumand,innocase,shouldmorethan2lboxalicacidperacrebe
used.
40CFR180.1001(c)(7/1/90)
fromHSDB
11.7.13 PersonalProtection
Skin:Preventskincontact
Eyes:Preventeyecontact
Washskin:Whencontaminated
Remove:Whenwetorcontaminated
Change:Daily
Provide:Eyewash Moreinformation...
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11.7.14 RespiratorRecommendations
NIOSH/OSHA
Upto25mg/m3:(APF=25)Anysuppliedairrespiratoroperatedinacontinuousflowmode(APF=25)Any
powered,airpurifyingrespiratorwithahighefficiencyparticulatefilter.
Upto50mg/m3:(APF=50)Anyairpurifying,fullfacepiecerespiratorwithanN100,R100,orP100filter.Click
hereforinformationonselectionofN,R,orPfilters.(APF=50)Anyselfcontainedbreathingapparatuswithafull
facepiece(APF=50)Anysuppliedairrespiratorwithafullfacepiece
Upto500mg/m3:(APF=2000)Anysuppliedairrespiratorthathasafullfacepieceandisoperatedinapressure
demandorotherpositivepressuremode
EmergencyorplannedentryintounknownconcentrationsorIDLHconditions:(APF=10,000)Anyselfcontained
breathingapparatusthathasafullfacepieceandisoperatedinapressuredemandorotherpositivepressuremode
(APF=10,000)Anysuppliedairrespiratorthathasafullfacepieceandisoperatedinapressuredemandorother
positivepressuremodeincombinationwithanauxiliaryselfcontainedpositivepressurebreathingapparatus
Escape:(APF=50)Anyairpurifying,fullfacepiecerespiratorwithanN100,R100,orP100filter.Clickherefor
informationonselectionofN,R,orPfilters.Anyappropriateescapetype,selfcontainedbreathingapparatus
Moreinformation...
11.7.15 FirePrevention
NOopenflames.
fromILOICSC
11.7.16 ExposurePrevention
PREVENTDISPERSIONOFDUST!
fromILOICSC
11.7.17 InhalationPrevention
Useventilation(notifpowder),localexhaustorbreathingprotection.
fromILOICSC
11.7.18 SkinPrevention
Protectivegloves.Protectiveclothing.
fromILOICSC
11.7.19 EyePrevention
Wearfaceshieldoreyeprotectionincombinationwithbreathingprotection.
fromILOICSC
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11.7.20 IngestionPrevention
Donoteat,drink,orsmokeduringwork.Washhandsbeforeeating.
fromILOICSC
11.7.21 ProtectiveEquipmentandClothing
...EYE&SKINPROTECTION/MUST/BEPROVIDEDFORPERSONSWORKINGWITHOXALICACID.
InternationalLabourOffice.EncyclopediaofOccupationalHealthandSafety.Vols.I&II.Geneva,Switzerland:International
LabourOffice,1983.,p.984
fromHSDB
Wearspecialprotectiveclothingandpositivepressureselfcontainedbreathingapparatus./Oxalicaciddihydrate/
fromHSDB
Ifmistsofoxalicacidshouldbeencounteredfromhotsolutions...adequateventilationshouldbeprovidedor
properrespiratoryprotectivedevicesworn.
fromHSDB
Respiratorfordustormistprotectionrubber,neoprene,orvinylgloveschemicalsafetyglassesrubbers,over
leatherorrubbersafetyshoesapronorimperviousclothingforsplashprotection.
U.S.CoastGuard,DepartmentofTransportation.CHRISHazardousChemicalData.VolumeII.Washington,D.C.:U.S.
GovernmentPrintingOffice,19845.
fromHSDB
Wearappropriatepersonalprotectiveclothingtopreventskincontact.
fromHSDB
Wearappropriateeyeprotectiontopreventeyecontact.
fromHSDB
Eyewashfountainsshouldbeprovidedinareaswherethereisanypossibilitythatworkerscouldbeexposedtothe
substancethisisirrespectiveoftherecommendationinvolvingthewearingofeyeprotection.
fromHSDB
Recommendationsforrespiratorselection.Maxconcnforuse:25mg/cum.RespiratorClass(es):Anysuppliedair
respiratoroperatedinacontinuousflowmode.Eyeprotectionneeded.Anypowered,airpurifyingrespiratorwitha
dustandmistfilter.Eyeprotectionneeded.
fromHSDB
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Recommendationsforrespiratorselection.Maxconcnforuse:50mg/cum.RespiratorClass(es):Anyairpurifying,
fullfacepiecerespiratorwithahighefficiencyparticulatefilter.Anyselfcontainedbreathingapparatuswithafull
facepiece.Anysuppliedairrespiratorwithafullfacepiece.
fromHSDB
Recommendationsforrespiratorselection.Maxconcnforuse:500mg/cum.RespiratorClass(es):Anysuppliedair
respiratorthathasafullfacepieceandisoperatedinapressuredemandorotherpositivepressuremode.
fromHSDB
Recommendationsforrespiratorselection.Condition:EmergencyorplannedentryintounknownconcnorIDLH
conditions:RespiratorClass(es):Anyselfcontainedbreathingapparatusthathasafullfacepieceandisoperatedin
apressuredemandorotherpositivepressuremode.Anysuppliedairrespiratorthathasafullfacepieceandis
operatedinapressuredemandorotherpositivepressuremodeincombinationwithanauxiliaryselfcontained
breathingapparatusoperatedinpressuredemandorotherpositivepressuremode.
fromHSDB
Recommendationsforrespiratorselection.Condition:Escapefromsuddenlyoccurringrespiratoryhazards:
RespiratorClass(es):Anyairpurifying,fullfacepiecerespiratorwithahighefficiencyparticulatefilter.Any
appropriateescapetype,selfcontainedbreathingapparatus.
fromHSDB
11.8 StabilityandReactivity
11.8.1 AirandWaterReactions
Watersoluble.Hygroscopic
fromCAMEOChemicals
11.8.2 ReactiveGroup
Acids,Carboxylic
fromCAMEOChemicals
11.8.3 ReactivitiesandIncompatibilities
Reactswithstrongalkalies,strongoxidizingmaterials,chlorites,andhypochlorites./Oxalicaciddihydrate/
fromHSDB
Strongoxidizers,silvercompounds,strongalkalis,chlorites[Note:Givesoffwaterofcrystallizationat215degrees
Fandbeginstosublime].
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fromHSDB
Strongoxidizers,silvercompounds,strongalkalis,chlorites[Note:Givesoffwaterofcrystallizationat215Fand
beginstosublime.]
STABILITY:Thischemicalishygroscopicandsensitivetoheat.Solutionsofthischemicalshouldbestablefor24
hoursundernormallabconditions.REACTIVITY:Thiscompoundmayreactviolentlywithfurfurylalcohol,silver,
sodium,perchlorate,sodiumhypochlorite,strongoxidizers,sodiumchlorite,acidchlorides,metalsandalkalimetals.
(NTP,1992)
11.9 TransportInformation
11.9.1 DOTLabel
Corrosive
fromCAMEOChemicals
11.9.2 PackagingandLabelling
Donottransportwithfoodandfeedstuffs.
fromILOICSC
11.9.3 ECClassification
Symbol:XnR:21/22S:(2)24/25
fromILOICSC
11.9.4 UNClassification
UNHazardClass:8UNPackGroup:III
fromILOICSC
11.9.5 EmergencyResponse
NFPACode:H3F1R0.
fromILOICSC
11.10 RegulatoryInformation
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11.10.1 FIFRARequirements
Residuesofoxalicacidareexemptedfromtherequirementofatolerancewhenusedasacalciumchelatinghard
waterinhibitorinaccordancewithgoodagriculturalpracticesasinert(oroccasionallyactive)ingredientsinpesticide
formulationsappliedtogrowingcropsortorawagriculturalcommoditiesafterharvest.Limits:Nomoreoxalicacid
shouldbeusedthanisnecessarytochelatecalciumand,innocase,shouldmorethan2lboxalicacidperacrebe
used.
40CFR180.1001(c)(7/1/90)
fromHSDB
11.11 OtherSafetyInformation
11.11.1 ToxicCombustionProducts
Combustionmayproduceirritantsandtoxicgases,includingformicacid./Oxalicaciddihydrate/
fromHSDB
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12 Toxicity
12.1 ToxicologicalInformation
12.1.1 ExposureRoutes
Thesubstancecanbeabsorbedintothebodybyinhalationofitsaerosolandbyingestion.Seriouslocaleffectsby
allroutesofexposure.
fromILOICSC
inhalation,ingestion,skinand/oreyecontact
12.1.2 Symptoms
irritationeyes,skin,mucousmembraneeyeburnslocalizedpain,cyanosisshock,collapse,convulsionskidney
damage
12.1.3 TargetOrgans
Eyes,skin,respiratorysystem,kidneys
12.1.4 Interactions
AnumberofsulfhydrylcompoundswereshowntoinhibitCO2andoxalateformationfromglyoxylatebyratliver
homogenatesandhepatocytes.Themostsignificantinhibitionoccurredwithcysteineandthisinhibitionwas
concentrationdependent.Inratsmadehyperoxaluricbyadministeringethyleneglycolintheirdrinkingwater,daily
intraperitonealinjectionsofcysteinecausedarapidandmarkeddecreaseinurinaryoxalateexcretionwhichwas
maintainedoverthedurationofthetreatment(28days).Overthistimeperiod,thelevelofurinaryoxalateexcretion
intheseethyleneglycoltreatedratswasreducedtothatofthecontrols.Itispostulatedthatthedecreaseisdueto
theformationofacysteineglyoxylateadduct,2carboxy4thiazolidinecarboxylate,whichpreventsglyoxylatebeing
furtheroxidizedtooxalate.Cysteineorsimilarsulphydrylcompoundsmaythereforehavepotentialastherapeutic
agentsinthepreventionofrenalstones. Abstract:PubMed
BaisRetalJUrol145(6):13025(1991)
fromHSDB
ThestudywasconductedtoinvestigatetheeffectofvitaminA,B1andB6deficiencyonoxalatemetabolismin
rats.Asignificanthyperoxaluriawasthecommonobservationinallthethreevitamindeficiencies(vitaminB6
greaterthanvitaminAgreaterthanvitaminB1).Theactivitiesofhepaticglycolateoxidaseandglycolate
dehydrogenaseweremarkedlyenhancedinvitaminAandvitaminB6deficientrats.However,lactate
dehydrogenaselevelsremainedunalteredinthesedeficienciesascomparedtotheirrespectivepairfedcontrols.
VitaminB1deficiencyof4weeksdurationcouldaugmenttheactivityofglycolateoxidaseonly,withnoalterations
intheglycolatedehydrogenaseandlactatedehydrogenaselevels.Intestinaloxalateuptakestudiesrevealed
increasedbioavailabilityofoxalatefromthegutinvitaminAandvitaminB6deficientrats.Thus,theresultssuggest
therelativecontributionofbothexogenousaswellasendogenousoxalateintheprocessofcalculogenesisunder
variousnutritionalstressconditionsinrat. Abstract:PubMed
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SharmaSetalAnnNutrMetab34(2):10411(1990)
fromHSDB
HyperoxalemiacanbeaggravatedbyvitaminCsupplementationinregularhemodialysispatients.Thepresent
studywasundertakentoexaminethevalidityofthisobservationinanexperimentalsetting.Fiftyfivesixths
nephrectomizedratsweredividedintotwogroups:30ratswereallowedfreeaccesstowatercontaining8mg/mlof
vitaminC(100160mg/100g/24hr)andtheremaindergiventapwaterwithoutvitaminC.Theserumcreatinine
increasedandthehematocritdecreasedgraduallyhowever,therewasnodifferencebetweenthetwogroups.
PlasmavitaminC,oxalateandurinaryoxalatelevelswerehigherinthevitamintreatedgroupthanthenontreated
rats.Histologicalexaminationrevealedglomerularandinterstitialfibrosisandroundcellinfiltrationaswellastubular
cystformation.OxalatedepositsinrenaltubuleswerefoundonlyinvitaminCtreatedratswithadvancedrenal
failure.Nontreatedanimalswithequallyadvancedrenalimpairmentshowednooxalatedeposits.Theseresults
confirmpreviousclinicalfindingsthatvitaminCsupplementationaggravatesthesecondaryoxalosisofchronicrenal
failure. Abstract:PubMed
OnoKetalNephron51(4):5369(1989)
fromHSDB
MaleWistarstrainratswhichhadbeenfedaglycolicaciddietdevelopedseverenephrocalcinosiswithurinary
calculiwithin4weeks.Ratsfedthesamedietwithcitratesaltsaddedhad,however,eitherslightorno
nephrocalcinosiswithoutanystonesintheurinarysystem.Nephrocalcinosisintermediatebetweenthoseinthe
citrategroupsandtheglycolicacidgroup,withsomeurinarycalculi,wasobservedinthecitricacidgroup.During
theexperiment,theurinaryoxalateconcentrationincreasedmarkedlyandwashigherinthecitrateandcitricacid
thanintheglycolicacidgroup.Theurinarycitrateconcentrationwassignificantlyhigherinthecitrategroupsand
lowerinthecitricacidandglycolicacidgroups.Therefore,citratesaltscanbeconcludedtoinhibitnephrocalcinosis
andcalculiformationasaresultofdecreasedurinarysaturationbymeansofincreaseinurinarycitrate,inspiteofa
slightincreaseintheurinaryoxalate. Abstract:PubMed
OgawaYetalHinyokikaKiyo33(11):17727(1987)
fromHSDB
Theadditionofoxalatetobloodstoredincitratephosphatedextroseproducesamarkedimprovementin2,3
diphosphoglyceratepreservationanincreasein2,3diphosphoglyceratelevelscanalsobedocumentedinshort
termincubationstudies.Oxalateisapotentinvitroinhibitorofredcelllactatedehydrogenase,
monophosphoglyceratemutase,andpyruvatekinase.Inthepresenceoffructose1,6diphosphatethelatter
inhibitoryeffectiscompetitivewithphospho(enol)pyruvate.Determinationofthelevelsofintermediatecompounds
inredcellsincubatedwithoxalatesuggestthepresenceofinhibitionatthepyruvatekinasestep,indicatingthatthis
isthesiteofoxalateaction.Apparentinhibitionattheglyceraldehydephosphatedehydrogenasestepisapparently
duetoanincreaseintheNADH/NADratio.Oxalatehadnoeffectontheinvivoviabilityofrabbitredcellsstoredin
citratephosphatedextrosepreservativesfor21days.Greaterunderstandingofthetoxicityofoxalateisrequired
beforeitcanbeconsideredsuitableasacomponentofpreservativemedia,butappreciationofthemechanismby
whichitaffects2,3diphosphoglyceratelevelsmaybeimportantindesignofotherbloodadditives.Malonate,the3
carbondicarboxylicacidanalogofoxalatedidnotinhibitpyruvatekinasenoraffect2,3diphosphoglyceratelevels.
Abstract:PubMed
BeutlerEetalBlood70(5):138993(1987)
fromHSDB
Twentytworecurrentcalciumstoneformershad24hrurinaryoxalateexcretionsontheirhomedietswhichwere
significantlygreaterthanthoseof30normalsubjects(0.48+or0.23mmol/daymean+orstandarddeviation
comparedwith0.31+or0.11p<0.01).Thestoneformersalsodemonstratedmarkeddaytodayvariabilityin
oxalateexcretionindicatingthatasinglenormalurinaryoxalatemeasurementdidnotexcludesignificant
hyperoxaluriaatothertimes.Onahospitaldietcontaining1000mgcalciumperday,urinaryoxalateexcretionfell
significantlyfrom0.48+or0.23mmol/dayto0.32+or0.12(p<0.01).Astheurinarycalciumexcretioninand
outofhospitalwassimilar,itseemsunlikelythatlowcalciumintakeathomewasresponsibleforthehyperoxaluria.
Allpatientshadrecurrentsymptomaticstonediseaseandhadbeenadvisedtoavoidfoodsrichinoxalate.Whilst
poorcomplianceisapossibleexplanationforthevariabilityinoxalateexcretion,itismorelikelythatthereisan
inadvertentintakeofoxalogenicprecursorsintheirdiet.Asnormalsubjectsdonotdemonstratehyperoxaluriaon
similarhomediets,stoneformersmayhaveametabolicdefectinthehandlingoftheseprecursors. Abstract:
PubMed
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BrownJMetalAnnClinBiochem24(Pt4):38590(1987)
fromHSDB
12.1.5 AntidoteandEmergencyTreatment
Treatmentshouldberapidlyinstitutedbygivingadilutesolutionofcalciumlactate,limewater,finelypulverized
chalk,plaster,and/ormilktosupplylargeamountsofcalciumtoinactivateoxalatebyforminganinsolublecalcium
saltinthestomach.Gastriclavageiscontroversial,sincethismaycompoundanalreadyseverecorrosivelesionin
theesophagusorstomach.However,ifused,gastriclavageshouldbedonewithlimewater(calciumhydroxide).
Intravenousgluconateorcalciumchloridesolutionsshouldbegiventopreventhypocalcemictetanyinseverecases
parathyroidextractalsohasbeengiven....Additionally,acuterenalfailureshouldbeanticipated,andcarefulfluid
managementisnecessary./Oxalates/
Haddad,L.M.,ClinicalManagementofPoisoningandDrugOverdose.2nded.Philadelphia,PA:W.B.SaundersCo.,1990.,p.
702
fromHSDB
Metabolicallyitstoxicityisbelieved/tobe/duetothecapacityofoxalicacidtoimmobilizecalciumandthusupset
thecalciumpotassiumratioincriticaltissues.Effectivetherapyagainstburnsfromoxalicacidinvolvesreplacement
ofcalcium.
fromHSDB
12.1.6 MedicalSurveillance
CAREFULCONSIDERATIONSHOULDBEGIVENTOPLACEMENTOFANYINDIVIDUALSWHOHAVE
PERIPHERALVASCULARDISEASEOFTHEHANDS,&ITWOULDSEEMBESTTOAVOIDEXPOSUREOF
SUCHPERSONSTOOXALICACID....
fromHSDB
12.1.7 HumanToxicityExcerpts
SYMPTOMATOLOGY:1.BURNINGPAININTHROAT,ESOPHAGUS,&STOMACH.EXPOSEDAREASOF
MUCOUSMEMBRANETURN...OPAQUEWHITE...2.VOMITING(OFTENBLOODYORWITHCOFFEE
GROUNDAPPEARANCE),INTENSEBURNINGPAIN,SEVEREPURGING.3.PULSEBECOMESWEAK,
IRREGULAR,SOMETIMESIMPERCEPTIBLE.HYPOTENSIONANDUSUALSIGNSOFCARDIOVASCULAR
COLLAPSEAPPEAR.4.IFDEATHISDELAYEDFORFEWHR,NERVOUSORNEUROMUSCULAR
SYMPTOMSDEVELOP:HEADACHE...TETANY,SOMETIMESCONVULSIONS,STUPOR,COMA,AND
DEATH.5.RENALDAMAGE,ASEVIDENCEDBYOLIGURIA,ALBUMINURIA,ANDHEMATURIA,MAY
PERSISTFORWEEKS./ORALOXALATE/
Gosselin,R.E.,R.P.Smith,H.C.Hodge.ClinicalToxicologyofCommercialProducts.5thed.Baltimore:WilliamsandWilkins,
1984.,p.III327
fromHSDB
CHRONICSKINEXPOSURETOSOLNOFOXALICACID.../HAS/BEENREPORTEDTOHAVECAUSED
LOCALIZEDPAIN&CYANOSISINFINGERSOREVENGANGRENOUSCHANGES...APPARENTLYDUE
TOLOCALIZEDABSORPTION...&RESULTANTARTERITIS.
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THENEUROMUSCULAREFFECTSCANBEEXPLAINEDLARGELYBYCALCIUMCOMPLEXINGACTIONOF
OXALATE,WHICHDEPRESSESTHELEVELOFIONIZEDCALCIUMINBODYFLUIDS.THIS
HYPOCALCEMIAPRODUCESSEVEREDISTURBANCESINACTIONSOFHEART&NERVOUSSYSTEM
DEATHMAYRESULT.../OXALATE/
1984.,p.II71
fromHSDB
...HASCAUSEDBURNSOFHUMANEYE...WHENSOLNACCIDENTALLYCAMEINCONTACTWITHEYE.
Grant,W.M.ToxicologyoftheEye.3rded.Springfield,IL:CharlesC.ThomasPublisher,1986.,p.685
fromHSDB
TOXICBYINHALATIONANDINGESTION,STRONGIRRITANT.
Sax,N.I.andR.J.Lewis,Sr.(eds.).Hawley'sCondensedChemicalDictionary.11thed.NewYork:VanNostrandReinholdCo.,
1987.,p.862
fromHSDB
Oxalicacidisregardedasastrongpoisonwhentakeninternallyaslittleas5gramshaveprovedfatal.
fromHSDB
Oxalateproductionbymoldsinfectingmaizesilagearebelievedtohavecausedintoxicationinahorse./Oxalates/
Humphreys,D.J.VeterinaryToxicology.3rded.London,England:BailliereTindell,1988.,p.200
fromHSDB
Symptoms:Local:Conjunctivitis,cornealdamagegangrenousulcerationsofskin.Inhalation:Irritationofrespiratory
tractulcerationofmucousmembranes,epistaxis,headache,nausea,vomiting,muscularirritability,weakness,
albuminuria.Swallowing:Burning&corrosionofthemouth,esophagus,stomachnausea&vomitingwith
hematemesisabdominalpain,diarrhea,bloodystool,numbness&tinglingoffingers&toesmuscularirritability,
tetany,convulsionsshock,oliguria,anuria,hematuria,albuminuriacardiacirregularities&circulatorycollapse.
1988.,p.388
fromHSDB
Studieswithbothunlabeledandlabeledagentsinhumanshaveprovidedbothstrongcircumstantialanddirect
evidencefortheexistenceofminorpathwaysofcarbohydratemetabolismandofoxidativedealkylationand
dehalogenationreactionsindrugbiotransformationsthatlinkxylitol,glycerol,polysorbateemulsifiers,
methoxyflurane,andpossiblydichloroacetatetoendogenousoxalateproduction.Becauseurinaryoxalateisnow
consideredtobeacriticalfactorinstoneformationandbecauseitisincreasinglyacceptedthat8090%ofurinary
oxalateisproducedendogenously,itisnowpossibletoformulatepathwaysthatlinkoxalateproductionwithdietary
macronutrients.Therapeuticmodificationsofdiet,invivohormonalmilieu,andintracellularmetaboliccontrolsin
relationtoendogenousoxalateproductionmayprovidenewformsoftreatmentforurolithiasis. Abstract:PubMed
ConyersRAetalClinChem36(10):171730(1990)
fromHSDB
Patientswithchronicrenalfailurewhoundergohemodialysisexperienceacceleratedatherosclerosisandpremature
death.Sincetheendmetabolite,oxalicacid,accumulatesinplasmainproportiontotheseverityofrenalfailure,/a
studywasconductedtodetermine/whethersodiumoxalate(0to300uM)isanendothelialtoxinand,therefore,
mightenhanceatherogenesis.Exposuretouremiclevelsofoxalate(greaterthan30uM)for9to28daysdepressed
endothelialcellreplicationby33%to84%(mean+orstandarddeviation,54%+or15.7%,n=17experiments,p
=0.002).Incontrast,replicationoffibroblastsexposedto200uMoxalatefor45dayswasnotinhibited.The
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inhibitoryeffectofoxalateonendothelialcellreplicationwasbothdoseandtimedependent(bothp<0.0001)and
wasfirstdetected3to7daysaftertheinitialexposuretooxalate.Further,theinhibitoryeffectwasfullyreversible
uponremovalofoxalate,butonlyifexposurewaslimitedto5daysorless.Sodiumsaltsofothercarboxylicacids
(citric,succinic,glyoxylic,andmalonic200uM)aswellashydrochloricacid(200uM)didnotsuppressendothelial
cellreplication.Oxalatealsoinhibitedendothelialcellmigrationbuthadnoeffectonbasal,thrombininduced,or
arachidonateinducedprostacyclinproductionbyendothelialcells.Exposureofendothelialcellstosodiumoxalate
(200uM)foraslittleas24hratimeperiodsufficienttoinducedelayed,transientinhibitionofreplicationnot
detectableuntilapproximately1weekafterexposureinhibitedincorporationof(3)Hleucineintoproteinby40%(p=
0.009).Itwasconcludedthatsodiumoxalateactsasauremictoxin,inhibitingendothelialcellreplicationand
migration,functionswhichmaybeimportantforconstitutiveinhibitionofatherosclerosis. Abstract:PubMed
LevinRIetalArteriosclerosis10(2):198207(1990)
fromHSDB
Theefficacyoflongtermtherapywithallopurinol,100mg3timesdaily,inthepreventionofrecurrentcalcium
oxalatecalculiofthekidneywasevaluatedinadoubleblindplacebocontrolledstudyin60patients.Afterthestudy,
theplacebogrouphad63.4%fewercalculi,whereastheallopurinolgrouphad81.2%fewercalculi.Duringthestudy
period,themeanrateofcalculouseventswas0.26perpatientperyearintheplacebogroupand0.12inthe
allopurinolgroup.Whenthetreatmentgroupswerecomparedbyactuarialanalysis,theallopurinolgroupwasfound
tohaveasignificantlylongertimebeforerecurrenceofcalculi.Itwasconcludedthatallopurinoliseffectiveinthe
preventionofcalciumoxalatestonesinpatientswithhyperuricosuria. Abstract:PubMed
EttingerBetalNEnglJMed315(27):13869(1986)
fromHSDB
Theeffectsoflongtermtreatmentwithoralpotassiumcitrate,3080meq/day,werestudiedin37patients(aged
2868yr)withidiopathichypocitraturiccalciumoxalateneprholithiasisforaperiodof2yr.Potassiumcitrate
treatmentproducedasustainedincreaseinurinarycitrateexcretionfrominitiallylowvaluestowithinnormallimits.
UrinarypHrosesignificantlyandwasmaintainedat6.5to7.0.Alongwiththesechanges,urinarysaturationof
calciumoxalatedeclinedsignificantlytonormallimits.Furtherstoneformationceasedin89.2%ofpatientsduring
treatment,andthestoneformationratedeclinedfrom2.11to0.28stones/patientyr.Itwasconcludedthat
potassiumcitraterepresentsarationaltreatmentforpatientswithidiopathihypocitraturiccalciumoxalate
nephrolithiasisbecauseitprovidesphysiologiccorrection(restorationofnormalurinarycitrate)andinhibitsnew
stoneformation./Calciumoxalate/ Abstract:PubMed
PakCYC,FullerCAnnInternMed104(Jan):337(1986)
fromHSDB
A14.5yearoldboywithendstagerenalfailureduetofamilialprimaryhyperoxaluriaunderwentcadaverdonorrenal
transplantation.Thegraftfunctionwasstableforaperiodof22months,whilehewasonconventional
immunosuppressivetherapy(prednisoloneandazathioprine)andadditionaloralpyridoxine,phosphorus,and
magnesiumsupplementation.WhenCyclosporinAwasintroducedinsteadofazathioprine,thebloodlevelsof
oxalaterose,andoxalatedepositionintherenaltubulibecameevident.Theseobservationssuggestthat
CyclosporinAinterfereswithoxalatemetabolismand,therefore,shouldbegivenwithutmostcautioninpatients
withprimaryhyperoxaluria. Abstract:PubMed
DrachmanRetalChildNephrolUrol9(12):902(1988)
fromHSDB
A34yearoldwomandevelopedacrystallineretinopathyafter2yrofinhalationalabuseofmethoxyflurane.After
thewomandevelopedrenalfailure,arenalbiopsyshowedmultiplebirefringentcrystalsintherenaltubularlumens,
epithelialcells,andinterstitiumcompatiblewithcalciumoxalate.Multiplebrightyellowwhitecrystalswere
depositedthroughouttheretinaandattheleveloftheretinalpigmentepitheliumwitharetinalarterialand
periarterialpredilection./Calciumoxalate/ Abstract:PubMed
NovakMAetalRetina8(4):2306(1988)
fromHSDB
Duringthelast4yr27specimensofcalciumoxalatenephrolithiasisinpatientsreceivinglongtermtreatmentwith
piridoxilate,adrugcomposedofanequimolarcombinationofglyoxylateandpyridoxine,werecollected.Themean
durationoftreatmentwas3.6yr(range4monthsto10yr)andthemeandailydosewas580mgpiridoxilate,which
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contained160mgglyoxylate.Calculioftenrecurred,withanaveragenumberof9.9perpatient,andanopen
operation,shockwavelithotripsyorpercutaneousnephrolithotomywasrequiredin22patients(81%).Oxalate
excretionwas727+or246umoleperdaywhileonthedrugand382+or201umoleperdayafterthedrugwas
withdrawn.Whewellitewasthemajorcomponentofcalculiinallcasesbutthestonesexhibitedapeculiar
morphologicalarrangement,withmultiplesmallindentationsandafinemamillarystructure.Freshlyvoidedurine
specimenscontainedunusualcrystals,whichoninfraredspectroscopywerecomposedofcalciumoxalatetrihydrate,
avarietyofcrystalneverobservedpreviouslyinhumanurine.Piridoxilateinducedcalciumoxalatenephrolithiasisis
anewvarietyofmetabolicdruginducednephrolithiasis.Observationssuggestthatevenlargedosesofpyridoxine
maybeunabletopreventtheexcessiveproductionofoxalatefromglyoxylate. Abstract:PubMed
DaudonMetalJUrol138(2):25861(1987)
fromHSDB
12.1.8 NonHumanToxicityExcerpts
...OXALATEMAYUPSETCALCIUMMETABOLISMSUFFICIENTLYTOINTERFEREWITHMILK
PRODUCTIONANDBONEGROWTHINLACTATINGANDPREGNANTANIMALS./OXALATE/
Clarke,E.G.,andM.L.Clarke.VeterinaryToxicology.Baltimore,Maryland:TheWilliamsandWilkinsCompany,1975.,p.258
fromHSDB
...MOSTCOMMONEFFECTOFOXALATESISTOCAUSEKIDNEYDAMAGEOWINGTOBLOCKINGOF
TUBULESBYCRYSTALSOFCALCIUMOXALATE....OXALATESMAYCRYSTALLIZEOUTINBRAIN
TISSUE&CAUSESYMPTOMSOFPARALYSIS&OTHERDISORDERSOFCENTRALNERVOUSSYSTEM.
OXALATESMAYLEADTOBREAKDOWNOFREDBLOODCELLS./OXALATES/
fromHSDB
FIRSTSYMPTOMSINCLUDEDULLNESSANDLOSSOFAPPETITE.HEADISLOWERED&ANIMALIS
UNWILLINGTOKEEPWITHFLOCK.WITHACUTEPOISONINGTHEREMAYBESALIVATIONANDNASAL
DISCHARGEWITHPROGRESSIVEWEAKNESS,RAPIDSHALLOWBREATHINGANDCOLLAPSE.
/OXALATE/
fromHSDB
ATPOSTMORTEMANINVARIABLEFINDINGISACCUMULATIONOFCALCIUMOXALATECRYSTALSIN
KIDNEYSANDURINARYTRACT.LUNGSMAYBEDARKRED&FILLEDWITHBLOODANDTHEREMAYBE
PETECHIALORLARGERHEMORRHAGES./OXALATE/
fromHSDB
TOXICDOSEOFOXALICACIDTOTHEDOGISABOUT1G&TOTHECAT,ABOUT0.2G.
fromHSDB
INATTEMPTSTOINDUCEOXALATEPOISONINGINHORSES...2DOSESOF454GOFOXALICACID,
SODIUMOXALATEORAMMONIUMOXALATE/HADTOBEGIVEN/WITHIN24HR,OR200GOF
AMMONIUMOXALATEDAILYFOR5DAYSINORDERTOKILLTHEANIMALS.DOSEOF200GOFOXALIC
ACID/DAYFOR8DAYSINDUCEDNONFATALPOISONING....
fromHSDB
DOSEOF340GOFHALOGETONOR900GOFGREASEWOOD/BOTHOXALATECONTAININGPLANTS/
ISALETHALDOSEFORAFASTINGSHEEP.
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fromHSDB
MALE&FEMALELONGEVANSRATSMAINTAINEDFOR70DAYSONDIETSCONTAINING2.5&5.0%
OXALICACIDHADDECRBODYWT&RESTRICTEDGROWTHRATES.5.0%DEPRESSEDABSOLUTE
ORGANWTBUTENHANCEDORGAN/BODYWTRATIO.VAGINALSMEARSINDICATEDDISRUPTED
ESTROUSCYCLES. Abstract:PubMed
GOLDMANETALRESCOMMUNCHEMPATHOLPHARMACOL18(2):369(1977)
fromHSDB
SIGNIFICANTREDNINTHYROIDWT,24HRTHYROIDUPTAKEOF(125)I&PLASMARADIOACTIVITY
OBSERVEDWITHINCRINPLASMATHYROIDSTIMULATINGHORMONEINLONGEVANSRATS
INGESTINGDIETARY5.0%OXALICACID.5.0%CANLEADTOHYPOTHYROIDISM.INCRIN
TRIIODOTHYRONINE. Abstract:PubMed
GOLDMANM,DOERINGGJTOXICOLAPPLPHARMACOL48(3):409(1979)
fromHSDB
2SHEEP&1COWCHANGEDFROMALFALFAHAYTODIETSWITH12%WT/WTOXALICACID.ADAPTED
ANIMALSTOLERATEDOXALATEWITHOUTSIGNSOFTOXICITY.HOWEVER,2OTHERSHEEPDIED
BECAUSETHEYWEREUNABLETOTOLERATETHEINFUSIONOFINCRAMTOFSODIUMOXALATE
INTOTHERUMENS. Abstract:PubMed
ALLISONETALJANIMSCI45(5):1173(1977)
fromHSDB
Oxaliscernua(OxalispescapraeBermudabuttercup,soursob)hascausedchronicoxalatepoisoninginsheepin
Australia.ThisplantoftencausesintoxicationinsheepgrazinginoliveorchardsinSardiniawhereitgrowsfreely.
Calvesfedexclusivelyonmilkfromcowsgiventhisplanthavebeenreportedtohavedevelopedcatarrhalenteritis,
markedeosinophilia,submucosalintestinalhemorrhages,folliculitisofthemesentericlymphnodesandnephrosis
withcrystallinedeposits./Oxalates/
fromHSDB
Theoxalatecontentofplantsishighestattheleafystageofgrowth,andplantswhicharenormallynotdangerous
tostockmaybecomesoatcertaintimesoftheyear.Halogetonmaycontainasmuchas34.5%ofoxalate,
mangelsupto12%andsoursob5.9%(dryweight).Unfortunately,mostoxalatecontainingplantsareverypalatable
tostock.Althoughsugarbeettopsareharmfultoanimalswhenfresh,theycanbefedwithoutilleffectoncethe
topshavewilted.Thisissaidtobeduetoconversionofharmfulsolublesaltsintoharmlessinsolubleonesduring
theprocess,butthereiscontraryevidenceonthispointandthequestioniscomplicatedbythefactthatoxalateis
nottheonlytoxicsubstanceinsugarbeettopstheycancontainlethalquantitiesofnitrate./Oxalates/
fromHSDB
2SHEEP&1COWCHANGEDFROMALFALFAHAYTODIETSWITH12%OXALICACID.10FOLD&
GREATERINCRININVITRORATEOFOXALATEMETABBYRUMINALMICROBES.OXALATE
DEGRADINGCAPACITYNEGLIGIBLEINCELLFREERUMINALFLUIDOFADAPTEDSHEEPBUTASSOC
WITHFRACTIONSWITHBACTERIALCELLS. Abstract:PubMed
ALLISONETALJANIMSCI45(5):1173(1977)
fromHSDB
Tenof100matureeweswereafflictedwithacuteoxalatetoxicosiswithin40hoursafterbeingtemporarilypenned
inalotthatcontainedconsiderablegrowingRumexcrispus(curlydock).Clinicalsignsoftoxicosisincludedexcess
salivation,tremors,ataxia,andrecumbency.Affectedewesweremarkedlyhypocalcemicandazotemic.Oxalate
crystalswerenotobservedinurine.Grosspostmortemlesionswereminimalandnondiagnosticin2ewesthatdied
peracutely,butperirenaledemaandrenaltubulardegenerationwereclearlyobservableineweseuthanatizedonthe
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thirddayoftoxicosis.Diagnosisofoxalatetoxicosiswasconfirmedbyhistopathologicfindings.SamplesofRumex
sppcontained6.6to11.1%oxalicacidonadryweightbasis,aconcentrationcomparablewiththatinotheroxalate
containingplantsthathavecausedacuteoxalatetoxicosis. Abstract:PubMed
PancieraRJetalJAmVetMedAssoc196(12):19814(1990)
fromHSDB
Inaperiodof21days,sixsubcutaneousinjectionsofcalciumchlorideanddibutyloxalatesolutionproduceda
flecklike,polymorphouscornealopacityandaslightstromalcloudinginchinchillarabbits,asseenwiththeslitlamp.
Infrontoftheendothelium,opaquestructurescouldbeseenwiththespecularmicroscope.NewZealandwhite
rabbitsshowedonlyadiffusecornealclouding.Lightmicroscopyrevealedareticularalterationofthecytoplasmin
thebasallayersofthecornealepitheliumprimarilyinchinchillabastardrabbits.Incentralcornealareasanirregular
structureofthebasalepithelialcellsandapapillalikealterationofthestromalepithelialborderwasseen.Inthe
endotheliumanincreasedformationofvacuoleswasobservedinbothspecies.Scanningelectronmicroscopy
demonstratedendothelialcellloss./Dibutyloxalate/ Abstract:PubMed
WeberUetalGraefesArchClinExpOphthalmol224(5):44751(1986)
fromHSDB
Depositionofcalciumoxalateisresponsibleforthepathologicmanifestationsofoxalosisandmaycontributeto
multiorgandysfunctioninuremiaandtotheprogressionofrenaldamageafterrenalfailureisestablished.Arat
modelofoxalosisusingasingleintravenousinjectionofsodiumoxalate,0.3mmol/kgbodyweight,inratshasbeen
developed.Polarizedlightmicroscopyandsectionfreezedryautoradiographywereusedtoidentify(14)Coxalate
withintherenalparenchymaandinextrarenalorgans.(14)Coxalatecrystalsunder3uinlengthwereidentified
withinoneminofinjectioninproximaltubulelumens.Sectionfreezedryautoradiographyshowedoccasionalminute
crystalswithinglomeruli,heart,lungandliveratonehr.Incontrasttoconcentrativecellularuptakedemonstratedin
ratrenalcorticalslicesinvitro,intracellularaccumulationof(14)Coxalatecouldnotbedetectedinvivo.Withinthe
first24hr,renaloxalateretentionreachedamaximumof25+or4%oftheinjecteddose/gmkidneycomparedto
amaximumofonly7+or3%/gmkidneyafteripadministration.Althoughlessthan1%dose/gmkidney
remainedafteroneweek,crystalfragmentswerescatteredthroughoutthecortexandmedulla,oftensurroundedby
fociofinterstitialnephritis.Theretentionofcrystalsinkidneyandotherbodyorgansfollowingivoxalateprovidesa
modelofoxalosiswhichstimulatespathophysiologiceventsinavarietyofclinicalsituationscharacterizedby
transientlyorpersistentlyelevatedserumoxalate. Abstract:PubMed
BlumenfruchtMJetalJUrol135(6):12749(1986)
fromHSDB
12.1.9 NonHumanToxicityValues
LDLoDogoral1000mg/kg
1988.,p.388
fromHSDB
12.1.10 NationalToxicologyProgramReports
Oxalicacid(OA)ametaboliteofethyleneglycol,wasselectedfortestingintheRACBprotocolbasedonthe
biologicalactivityoftheparentcompound....Datacollectedonbodyweights,clinicalsigns,&food/water
consumptionduringthedoserangefindingsegment(Task1)wereusedtosetconcnsforthemainstudy(Task2)at
0.05%,0.10%,&0.2%OAindrinkingwater.Theseconcnsreducedwaterconsumptioninthemiddle&highdose
groupsbyapprox25%,&yieldedcalculatedconsumptionestimatesofnearly=89,162,&275mgOA/kg/day.
Therewerenoadverseclinicalsigns.Onefemalediedinboththelow&middledosegroups.At0.2%OA,the
numberoflitters/pairwasreducedby5%&thepupweightadjustedforlittersizewasreducedbynearly=4%sire
&damweightswerenotaffectedduringTask2.ForthelastlitterborninTask2,bodyweights&pupnumberwere
recordedforthecontrols&0.1&0.2%OAgroupstherewerenotreatmentrelatedchangesinpupsurvivalor
weightgaintopostnatalday14.BecauseamodestdegreeofeffectseenatthetopdosegroupinTask2was
identifiedonlyaftersummingalltheTask2litterdata,itwaspredictedthatthesinglelitterproducedinTask3
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wouldbeinsufficienttohelpdeterminetheaffectedsex.Thus,thelastlitterfromthecontrol&highdoseanimals
wererearedfortestinginTask4,&Task3wasnotconducted.AftertheTask4micewereweaned,10F0mice
fromthecontrol&0.2%groupswerekilled&necropsied.Nochangeswereseeninbodyororganweightsfrom
females.Formales,theonlysignificanteffectwasa19%decrinprostateweightat0.2%OA.Totalcalciumlevels
inbloodweremeasuredfor10miceofeachsexinthecontrol&0.2%OAgroupsthecontrollevelof9.4mg/dl
wasunchangedbyOAconsumption.IntheTask4onewkmatingtrial,therewasa20%reductioninthenumberof
livepups/litterdeliveredbythe0.2%OAgroup.Nootherdifferenceswereobserved.After7daysofvaginallavage,
theF1micewerekilled&necropsied.Whileterminalbodyweightwasunchangedineithersex,femalekidney
weight(adjustedforbodyweight)wasincreasedby10%intheOAtreatedfemales.Therewerenootherchangesin
organweights.The%ofabnormalspermformsincreasedfrom2.2%incontrolsto4.0%inthe0.2%OAgroup.
Serumcalciumlevelsineithersexwereunchangedfromcontrollevelsof7.9mg/dl.Insummary,intheF0mice,
OAattheselevelsreducedwaterconsumption,&reducedthenumberoflitters/pair,adjustedpupweight,&
prostateweightintheabsenceofdetectedsomaticorganchanges.InF1mice,anincrinkidneyweightoccurred
concomitantwithareductioninthenumberoflivepups/litter,&increasedabnormalspermforms.Ifthekidney
weighteffectistheresultofreducedwaterconsumption,thenitcanbeconcludedthatOxalicAcidisareproductive
toxicantinSwissmiceatconcnsthatreduceparentalwaterconsumption,butthatcausefewothersomaticeffects.
DepartmentofHealth&HumanServices/NationalInstituteofEnvironmentalHealthSciences,NationalToxicologyProgram
OxalicAcid(CAS#144627):ReproductionandFertilityAssessmentinCD1MiceWhenAdministeredinDrinkingWater,NTP
StudyNo.RACB84064(September1985)Availablefrom,asofAugust14,2002:http://ntp.niehs.nih.gov/index.cfm?
objectid=0847F35A0850D1E7B02ED4DDD150F990
fromHSDB
12.2 EcologicalInformation
12.2.1 EnvironmentalFate/ExposureSummary
Oxalicacidisnaturallycontainedasthepotassiumorcalciumsaltinplants,vegetables,humanurine,animalurine,
andkidneystones.Itisalsotheproductofthemetabolismofmanymolds.Oxalicacidmaybereleasedtothe
environmentintobaccosmoke,automobileexhaust,rendering,inwastestreamsfrompulpbleaching,andby
photochemicaloxidationsofanthropogeniccompoundsduringlongrangetransport.Ifreleasedtosoil,oxalicacid
underenvironmentalconditions(pH59)willbeintheformoftheoxalateion(pKa1andpKa2of1.25and4.28,
respectively)andisexpectedtoleachinsoil.Photolysisisexpectedtobeanimportantfateprocessthedaytime
persistenceofoxalicacidonsoilsurfacesisnotexpectedtoexceedafewhours.Baseduponscreening
biodegradationtests,biodegradationinsoilisexpectedtobeimportant.Ifreleasedtowater,oxalicacidwillnot
volatilize,adsorbtosediment,bioconcentrateinaquaticorganisms,oxidizeorhydrolyze.Thepredominantaquatic
fateprocessesareexpectedtobephotolysisinsurfacewatersandaerobicandanaerobicbiodegradation.If
releasedtotheatmosphere,removalfromairviawetdeposition,drydeposition,andphotolysisislikelytooccur.
Exposureofthegeneralpopulationtooxalicacidisexpectedtooccurthroughconsumptionoffoodsinwhichitis
naturallycontained,inhalationofcontaminatedair,andconsumptionofcontaminatedgroundwater.Inoccupational
settings,exposuretooxalicacidmayoccurthroughinhalationofvaporsandthrougheyeandskincontact.(SRC)
fromHSDB
12.2.2 NaturalOccurringSources
MANYPLANTSCONTAINOXALATE,NOTABLYRHUBARBLEAVES,DIEFFENBACHIAORDUMBCANE,
BEETS,SPINACH,MANGOLD,HALOGETON,SORREL,PURSLANE,DOCK,GREASEWOOD&RUSSIAN
THISTLE./OXALATES/
1984.,p.III326
fromHSDB
PLANTSCONTAININGOXALATES:ATRIPLEXSPECIES,BETAVULGARIS,CALANDRINIASPECIES,
EMEXAUSTRALIS,ENCHYLAENATOMENTOSA,HALOGETONGLOMERATUS,OXALISSPECIES,
PORTULACASPECIES,RHEUMRHAPONTICUM,RUMEXSPECIES,SALSOLAKALI,SARCOBATUS
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VERMICULATUS,THRELKELDIAPROCERIFLORA,TRIANTHEMASPECIES./FROMTABLEOXALATES/
Clarke,M.L.,D.G.HarveyandD.J.Humphreys.VeterinaryToxicology.2nded.London:BailliereTindall,1981.,p.260
fromHSDB
Oxalicacidispresentinmanyplantsandvegetables,notablyinthoseoftheOxalisandRumexfamilies,whereit
occursintheleaves,roots,rhizomes,andsapoftheplantasthepotassiumorcalciumsalt(12).Forexample,
waterliliesandduckweedareoxylatecontainingplants(3)andthesefrequentlycolonizelakesandotheraquatic
environments.Furthermore,oxylatemayconstituteasmuchas50%ofthedryweightofsomeplantorgans,serving
bothanexcretoryandastoragefunctionbychelatingandprecipitatingexcesscalciumions(3).Itistheproductof
themetabolismofmanymolds(1).SeveralspeciesofPenicilliumandAspergillusconvertsugarintocalciumoxylate
with90%yieldsunderoptimumconditions(1).Italsooccursinhumanandanimalurineandthecalciumsaltisa
majorconstituentofkidneystones(2).
(1)WindholzMetalTheMerckIndex10thed.Rahway,NJ:Merck&CoIncp.991(1983)(2)BernalesCAetalKirkOthmer
EncyclChemTech.3rdNY:Wiley16:61836(1981)(3)SmithRL,OremlandRSApplEnvironMicrobiol46:10613(1983)
fromHSDB
12.2.3 ArtificialSources
Oxalicacidmaybereleasedtotheenvironmentasemissionsfromrendering,tobaccosmoke(1),andautomobile
exhaust(2).Oxalicacidmaybeproducedintheatmospherebyphotochemicaloxidationsofanthropogenic
compoundsduringlongrangetransport(3).Oxalicacidhasbeenidentifiedinpulpkraftmilleffluents(46)therefore,
itmaybereleasedtotheenvironmentinwastestreamsresultingfrompulpbleaching(SRC).Theestimated
emissionrateofoxalicacidintheSouthEastAirBasin,CAis87kg/day(7).
(1)GraedelTEetalAtmosphericChemicalCompoundsNY:AcademicPressp.346(1986)(2)KawamuraK,KaplanIR
EnvironSciTechnol21:10510(1987)(3)SatsumabayashiH,KuritaHAtmosphericEnviron24A:144350(1990)(4)SuntioLR
etalChemosphere17:124990(1988)(5)LindstromK,OsterbergFEnvironSciTechnol2:1338(1986)(6)KringstadKP,
LindstromKEnvironSciTechnol18:236A48A(1984)(7)GrosjeanDetalMeasurementsofOrganicAcidsintheSouthEast
AirBasin.StateofCaliforniaAirResourcesBoardNTISPB89145411p.43(1988)
fromHSDB
12.2.4 EnvironmentalFate
TERRESTRIALFATE:AnestimatedKocvalueof5(1,SRC)foroxalicacidindicateshighmobilityinsoil(2)and
oxalicacidhasbeendetectedingroundwater(3).Volatilizationfrommoistsoilsisnotexpectedtoberapidbased
uponalowHenry'sLawconstant.Severalscreeningstudiesindicaterapidbiodegradationofoxalicacid(48).
Althoughthesestudiesarenotspecifictosoilmedia,theysuggestthatoxalicacidwillreadilybiodegradeinsoil.
Theoxalicacidconcninanotherstudywasdeterminedtodecreasefrom30mg/kgonasoilsurfacetoabout6
mg/kg540cmbelowthesoilsurface(3)whichsuggeststhatbiodegradationmayhaveoccurred(SRC).Photolysisis
expectedtobeanimportantterrestrialfateprocessthedaytimepersistenceofoxalicacidonsoilsurfacesisnot
expectedtoexceedafewhours(9).
(1)LymanWJetalHandbookofChemicalPropertyEstimationMethods.WashingtonDC:AmerChemSocpp.49,510,74,
1515to1532(1990)(2)SwannRLetalResRev85:1728(1983)(3)CordtT,KussmaulHVomWasser74:28798(1990)(4)
GaffneyPE,HeukelekianHSewIndustWastes30:503(1958)(5)HeukelekianH,RandMCJWaterPollutContrAssoc29:
104053(1955)(6)MadsenEL,AlexanderMApplEnvironMicrobiol50:3429(1985)(7)TakemotoetalSuishitsuOdaku
Kenkyu4:8090(1981)(8)YoungetalJWaterPollutContrFed40:35468(1968)(9)GrosjeanDetalMeasurementsof
OrganicAcidsintheSouthCoastAirBasinARBR88/375PB89145441)GovRepAnnounceIndex(U.S.)89(9)AbstrNo.
921,946(1989)
fromHSDB
AQUATICFATE:Severalscreeningstudies(48)andgrabsampletests(9)indicatethatunderaerobicand
anaerobicconditions,oxalicacidwillreadilybiodegradeinaquaticecosystems.BasedonanexperimentalHenry's
Lawconstantof1.4X1010atmcum/moleat25degC(2),oxalicacidisexpectedtobeessentiallynonvolatilefrom
water(1).Adsorptiontosedimentandbioconcentrationinaquaticorganismsmaynotbeimportantfateprocesses
foroxalicacidinwatersystems.BasedonpKa1andpKa2valuesof1.25and4.28(3),respectively,oxalicacidwill
existprimarilyastheoxalateionunderenvironmentalconditions(pH59,SRC).Aquaticoxidationisnotlikelytobe
animportantfateprocessbasedonahalflifeof285yrsinwaterundercontinuoussunlight(3,SRC).Oxalicacid
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mayreactslowlyinwaterwithphotochemicallyproducedOHradicals,butitisexpectedtoberemovedrapidlyfrom
surfacewaterbydirectphotolysisthedaytimepersistenceofoxalicacidisnotexpectedtoexceedafewhours(10).
(1)LymanWJetalHandbookofChemicalPropertyEstimationMethods.WashingtonDC:AmerChemSocpp.49,510,154,
1515to1532(1990)(2)GaffneyJSetalEnvironSciTechnol21:51924(1987)(3)BuxtonGVetalJPhysChemRefData
17(2):517882(1988)(4)GaffneyPE,HeukelekianHSewIndustWastes30:503(1958)(5)HeukelekianH,RandMCJWater
PollutContrAssoc29:104053(1955)(6)MadsenEL,AlexanderMApplEnvironMicrobiol50:3429(1985)(7)Takemotoetal
SuishitsuOdakuKenkyu4:8090(1981)(8)YoungetalJWaterPollutContrFed40:35468(1968)(9)SmithRL,Oremland
RSApplEnvironMicrobiol46:106113(1983)(10)GrosjeanDetalMeasurementsofOrganicAcidsintheSouthCoastAir
BasinARBR88/375PB89145411GovRepAnnounceIndex(U.S.)89(9)AbstrNo.921,946(1989)
fromHSDB
ATMOSPHERICFATE:Basedonameasuredvaporpressureof2.34104mmHgat25degC(2),oxalicacidis
expectedtoexistalmostentirelyinthevaporphaseintheambientatmosphere(3).Inthevaporphase,oxalicacid
intheambientatmosphereisveryslowlydegradedbyreactionwithphotochemicallyformedhydroxylradicalsthe
halflifeforthisreactioninaircanbeestimatedtobeabout223days(1).Oxalicacidintheambientatmosphere
mayreactslowlywithOHradicals,butitisremovedrapidlybyphotolysisthedaytimepersistenceofoxalicacidis
notexpectedtoexceedafewhours(4).Basedonitshighwatersolubility,removalfromairviawetdepositionis
likelytooccur(4,SRC).Oxalicacidmayalsoberemovedfromairviadrydepositionwith11%ofthetotaldeposition
beingdrydeposition(4).
(1)AtkinsonREnvironToxicolChem7:43542(1988)(2)BernalesCAetalKirkOthmerEncyclChemTech.3rdNY:Wiley
16:61836(1981)(3)EisenreichSJetalEnvironSciTechnol15:308(1981)(4)GrosjeanDetalMeasurementsofOrganic
AcidsintheSouthCoastAirBasinARBR88/375PB89145411GovRepAnnounceIndex(U.S.)89(9)AbstrNo.921,946(1989)
fromHSDB
12.2.5 Biodegredation
Sixtestsatoxalicacidinitialconcnsof3.3to10ppmexhibited75to202%BODToveranincubationperiodof5
daysinanaerobicscreeningstudyusingsewageinoculum(1).A78and55.5%BODTforoxalicacidwasmeasured
underaerobicconditionsoveraperiodof5daysinscreeningtestsat20degCusingsewageinoculum(2).Oxalic
acidatinitialconcnsof0.00375,0.0375,and0.375ppmexhibited95,99,and100%degradation,respectively,in
anaerobicscreeningstudyat25degCusingsewageinoculum(3).Inanotherscreeningstudyusingsewage
inoculum,68and64%BODTweremeasuredforoxalicacidatinitialconcnsof10and20ppm,respectively,overa
5dayincubationperiod(4).An89%BODTwasmeasuredforoxalicacid(10ppminitialconcn)inanaerobic
screeningstudyusingsewageinoculumat19.520.5degCoveranincubationperiodof5days(5).
(1)GaffneyPE,HeukelekianHSewIndustWastes30:503(1958)(2)HeukelekianH,RandMCJWaterPollutContrAssoc29:
104053(1955)(3)MadsenEL,AlexanderMApplEnvironMicrobiol50:3429(1985)(4)TakemotoetalSuishitsuOdaku
Kenkyu4:8090(1981)(5)YoungetalJWaterPollutContrFed40:35468(1968)
fromHSDB
Ultimateanaerobicbiodegradationratesweredeterminedinamarinewater/sedimentgrabsampletakenfromasalt
marshinPaloAlto,CAtobe0.41,0.92,and0.76/daywhichcorrespondtoanaerobicdegradationhalflivesof1.7,
0.75,and0.9days,respectively.Inanothermarinewater/sedimentgrabsamplefromBigSodaLake,NV,anaerobic
biodegradationratesof0.004and0.22/dayweredeterminedwhichcorrespondtohalflivesof173and3.15days,
respectively.Usingthesamemethod(14CO2evolution,GC),ultimateanaerobicbiodegradationratesof0.55,0.31,
5.45,1.73,and1.96/day(halflivesof1.26,2.23,0.13,0.4,and0.35days,respectively)weremeasuredin
freshwater/sedimentgrabsamplestakenfromSearsvilleLake,PaloAlto,CA.Inafreshwater/sedimentgrab
sampletakenfromLakeTahoe,CA,ultimateanaerobicbiodegradationratesweremeasuredtobe0.01and
0.13/daywhichcorrespondtorespectivehalflivesof69and5.3day(1).[(1)SmithRL,OremlandRSApplEnviron
Microbiol46:10613(1983)] Fulltext:PMC239274 Abstract:PubMed
fromHSDB
12.2.6 AbioticDegredation
Therateconstantforthevaporphasereactionofoxalicacidwithphotochemicallyproducedhydroxylradicalscanbe
estimatedtobe7.2X1014cucm/moleculesecat25degCwhichcorrespondstoanatmospherichalflifeofabout
223daysatanatmosphericconcnof5X10+5hydroxylradicalspercucm(1,SRC).Acidsaregenerallyresistentto
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hydrolysis(4)therefore,oxalicacidisnotexpectedtohydrolyzeinaquaticenvironments.Basedondissociation
constantvaluespKa1andpKa2of1.25and4.28(1),respectivelyoxalicacidisexpectedtoexistasanionunder
environmentalconditions(pH59).Theaquaticoxidationrateforthereactionofhydroxylradicalsinwaterwiththe
oxalateionhasbeenexperimentallydeterminedtobe7.7X10+6L/molesatpH6(1).Basedonthisrateanda
hydroxylradicalconcnof1X1017mole/Linwaterundercontinuoussunlight(3),thehalflifefortheaquatic
oxidationofoxalicacidcanbeestimatedtobe285yrs(SRC).OxalicacidmayreactslowlywithOHinwater,butit
isremovedrapidlybydirectphotolysisthedaytimepersistenceofoxalicacidisnotexpectedtoexceedafew
hours(5).
(1)BuxtonGVetalJPhysChemRefData17:517882(1988)(2)AtkinsonREnvironToxicolChem7:43542(1988)(3)MillT
etalScience2078867(1980)(4)LymanWJetalHandbookofChemicalPropertyEstimationMethods.WashingtonDC:
AmerChemSocpp.49,54,510,74,75,1515to1532(1990)(5)GrosjeanDetalMeasurementsofOrganicAcidsinthe
SouthCoastAirBasinARBR88/375PB89145411GovRepAnnounceIndex(U.S.)89(9)AbstrNo.921,946(1989)
fromHSDB
12.2.7 Bioconcentration
Basedonanaverageexperimentalwatersolubilityof220,000mg/Lat25degC(1)andaregressionderived
equation(2),theBCFforoxalicacidcanbeestimatedtobeapproximately0.6(SRC)andthereforeshouldnotbe
expectedtobioconcentrateinaquaticorganisms(SRC).
(1)YalkowskySHetalArizonaDataBaseofWaterSolubility(1989)(2)LymanWJetalHandbookofChemicalProperty
EstimationMethods.WashingtonDC:AmerChemSocpp.49,54,510,74,75,1515to1532(1990)
fromHSDB
12.2.8 SoilAdsorption/Mobility
Basedonanaverageexperimentalwatersolubilityof220,000mg/Lat25degC(1)andaregressionderived
equation(2),theKocforundissociatedoxalicacidcanbeestimatedtobeapproximately5.ThisKocvalueindicates
thatoxalicacidwillhaveveryhighmobilityinsoil(3)therefore,adsorptiontosoilandsedimentmaynotbean
importantfateprocess.BasedonpKa1andpKa2valuesof1.25and4.28(4)respectively,oxalicacidwillexist
primarilyastheoxalateionunderenvironmentalconditions(pH59).Noexperimentaldataareavailableto
determinewhethertheoxalateionwilladsorbtosedimentorsoilmorestronglythanitsestimatedKocvalue
indicates(SRC).
(1)YalkowskySHetalArizonaDataBaseofWaterSolubility(1989)(2)LymanWJetalHandbookofChemicalProperty
EstimationMethods.WashingtonDC:AmerChemSocpp.49,54,510,74,75,1515to1532(1990)(3)SwannRLetalRes
Rev85:1728(1983)(4)BuxtonGVetalJPhysChemRefData17:517882(1988)
fromHSDB
12.2.9 VolatilizationfromWater/Soil
BasedonanexperimentalHenry'sLawconstantof1.4X1010atmcum/moleat25degC(1),oxalicacidis
essentiallynonvolatilefromwater(2).
(1)GaffneyJSetalEnvironSciTechnol21:51924(1987)(2)LymanWJetalHandbookofChemicalPropertyEstimation
Methods.WashingtonDC:AmerChemSocpp.49,54,510,74,75,1515to1532(1990)
fromHSDB
12.2.10 WaterConcentrations
GROUNDWATER:OxalicacidwasdetectedatasiteinGermanyataconcnofabout1mg/kgingroundwater610
to640cmbelowthesurfacehowever,itwasnotdetectedingroundwater640to670cmbelowthesurface(1).
(1)CordtT,KussmaulHVomWasser74:28798(1990)
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RAIN/SNOW:OxalicacidwasdetectedintwosamplesofmistcollectedinLosAngeles,CAonJune9,1983and
June11,1983atconcnsof23.3and4uM,respectively(1).Inthesamestudy,oxalicacidwasdetectedin4fog
samplesinJuneof1983atconcnsrangingfrom17.3to18.7uMatanaverageconcnof18uM(1).Also,oxalicacid
wasdetectedin8rainsamplescollectedinLosAngeles,CAinAugustandSeptemberof1983atconcnsranging
from2.8to20.7uMatanaverageconcnof15.9uM(1).
(1)SteinbergSetalInternJEnvironAnalChem19:25160(1985)
fromHSDB
12.2.11 EffluentsConcentrations
Oxalicacidhasbeenqualitativelydetectedinpulpmilleffluents(1).Oxalicacidwasidentifiedintwoprebleaching
spentliquorsofkraftpulpmilleffluentsatconcnsof0.5and6g/tonofpulp(2).Itwasdetectedduringkraftpulp
bleachingataconcnof130g/toninaspentchlorinationliquorand590g/toninaspentalkaliextractionliquor(3).
Oxalicacidwasidentifiedintheautomobileexhaustofa1982ToyotaCorollaataconcnof182nmole/cum(4).It
wasalsoidentifiedataconcnof482nmole/cuminautomobileexhaustfroma1971MercedesBenz(4).
(1)SuntioLRetalChemosphere17:124990(1988)(2)LindstromK,OsterbergFEnvironSciTechnol2:1338(1986)(3)
KringstadKP,LindstromKEnvironSciTechnol18:236A48A(1984)(4)KawamuraK,KaplanIREnvironSciTechnol21:105
10(1987)
fromHSDB
12.2.12 Sediment/SoilConcentrations
Oxalicacidwasdetectedatconcnsrangingfrom30to6mg/kginsoil0to540cm,respectively,belowthesurface
atasiteinGermany(1).Oxalicacidwasidentifiedin2soilsamplestakenfromtheUCLAcampus(LosAngeles,
CA)atconcnsof166and156nmol/g(2).Oxalicacidwasdetectedin2fractionsofbogsedimentfromtheLos
Angeles,CAareaatconcnsof1,410(humicacidfraction)and3,350(fulvicacidfraction)nmol/g(2).Significant
concnsofoxylate(dissolvedplusparticulate)werepresentinsedimentstakenfromadiversityofaquatic
environments,rangingfrom0.1to0.7mmol/lofsediment(3).Theseincludedpelagicandlittoralsedimentsfrom
twofreshwaterlakes(SearsvilleLake,CAandLakeTahoe,CA),ahypersaline,meromictic,alkalinelake(BigSoda
Lake,NV),andasouthSanFranciscoBaymudflatandsaltmarsh(3).
(1)CordtT,KussmaulHVomWasser74:28798(1990)(2)KawamuraK,KaplanIREnvironSciTechnol21:10510(1987)(3)
SmithRL,OremlandRSApplEnvironMicrobiol46:10613(1983)
fromHSDB
12.2.13 AtmosphericConcentrations
URBAN/SUBURBAN:OxalicacidwasthedominantspeciesofdicarboxylicacidsintherangeC2C10identifiedin
theLosAngeles,CAambientatmosphere(1).InJune,1984,oxalicacidwasdetectedinwestLosAngelesairat
concnsof6.38and2.12nmol/cum(1).OxalicacidwasdetectedinwestLosAngelesambientairin6samplesata
concnrangeof3.40to8.65nmol/cumandanaverageconcnof5.4nmol/cuminOctober,1984(1).Inthesame
studyduringOctoberof1984,itwasdetectedin2samplestakenfromdowntownLosAngelesatconcnsof6.60
and8.31nmol/cum(1).OxalicacidwasalsodetectedingreenhouseairatUCLA(LosAngeles,CA)inDecember
of1984atconcnsof1.31and2.83nmol/cum(1).OxalicacidwasdetectedinairborneaerosolsaboveTakasaki
andKaruizawa,Japanataverageconcnsof5.1and3.8ng/cum,respectively,duringJulyof1986(2).Oxalicacid
wasdetectedataconcnofapproximately3ng/cuminairborneparticulatematterinasuburbanareainJapan(3).
InSeptemberof1985,oxalicacidwasdetectedintheambientatmosphereofClaremont,CAin12of12samples
takenataconcnrangeof<0.12to0.94ug/cum(4).
(1)KawamuraK,KaplanIREnvironSciTechnol21:10510(1987)(2)SatsumabayashiH,KuritaHAtmosEnviron24A:1443
50(1990)(3)YokouchiY,AmbeYAtmosEnviron20:172734(1986)(4)GrosjeanDAtmosEnviron22:163748(1988)
fromHSDB
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12.2.14 FoodSurveyValues
occursinthesapoftheplantasthepotassiumorcalciumsalt(2).Oxalicacidwasqualitativelydetectedinraw
cassava(Manihotesculenta,Crantz)whichisoneofthemajorstaplefoodsofthetropics(1).GariandFarine
(Farinhademandioca),bothproductsofcassava,weredeterminetobe0.04%and0.2%oxalicacid,respectively(1).
(1)DouganJetalJSciFoodAgric34:87484(1983)(2)WindholzMetalTheMerckIndex10thedRahway,NJ:Merck&Co
Incp.991(1983)
fromHSDB
12.2.15 PlantConcentrations
OXALATECONTENTOFPLANTSISHIGHESTATLEAFYSTAGEOFGROWTH&PLANTSWHICHARE
NORMALLYNOTDANGEROUSTOSTOCKMAYBECOMESO@CERTAINTIMESOFYR.HALOGETON
MAYCONTAIN...34.5%OFOXALATE,MANGELSUPTO12%&SOURSOB5.9%(DRYWT)./OXALATE/
Clarke,M.L.,D.G.HarveyandD.J.Humphreys.VeterinaryToxicology.2nded.London:BailliereTindall,1981.,p.258
fromHSDB
occursintheleaves,roots,rhizomes,andsapoftheplantasthepotassiumorcalciumsalt(12).Forexample,
waterliliesandduckweedareoxylatecontainingplants(3).Furthermore,oxylatemayconstituteasmuchas50%of
thedryweightofsomeplantorgans,servingbothanexcretoryandastoragefunctionbychelatingandprecipitating
excesscalciumions(3).Oxylateconcnsrangedfrom0.1to5.0%inseveralplantspeciesthatarepotentialsources
oftheoxylatesinsedimentsofSearsvilleLake,CA,LakeTahoe,CA,BigSodaLake,NV,andasouthSan
FranciscoBaymudflatandsaltmarsh(3).
(1)WindholzMetalTheMerckIndex10thedRahway,NJ:Merck&CoIncp.991(1983)(2)BernalesCAetalKirkOthmer
EncyclChemTech.3rdNY:Wiley16:61836(1981)(3)SmithRL,OremlandRSApplEnvironMicrobiol46:10613(1983)
fromHSDB
12.2.16 AnimalConcentrations
Oxalicacidoccursinhumanandanimalurineandthecalciumsaltisamajorconstituentofkidneystones(1).
(1)BernalesCAetalKirkOthmerEncyclChemTech.3rdNY:Wiley16:61836(1981)
fromHSDB
12.2.17 OtherEnvironmentalConcentrations
OxalicacidwasidentifiedingreenhousedustanddustfromdowntownLosAngeles,CAataconcnsof2,330and
2,510nmol/g,respectively(1).
(1)KawamuraK,KaplanIREnvironSciTechnol21:10510(1987)
fromHSDB
12.2.18 ProbableRoutesofHumanExposure
Exposureofthegeneralpopulationtooxalicacidisexpectedtooccurthroughconsumptionoffoodsinwhichitis
naturallycontained,inhalationofcontaminatedairandconsumptionofcontaminatedgroundwater(17,SRC).In
occupationalsettings,exposuretooxalicacidmayoccurthroughinhalationofvaporsandthrougheyeandskin
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contact(SRC).
(1)KawamuraK,KaplanIREnvironSciTechnol21:10510(1987)(2)SatsumabayashiH,KuritaHAtmosphericEnviron24A:
144350(1990)(3)YokouchiY,AmbeYAtmosEnviron20:172734(1986)(4)GrosjeanDAtmosEnviron22:163748(1988)
(5)DouganJetalJSciFoodAgric34:87484(1983)(6)WindholzMetalTheMerckIndex10thedRahway,NJ:Merck&Co
Incp.991(1983)(7)CordtT,KussmaulHVomWasser74:28798(1990)
fromHSDB
NIOSH(NOHSSurvey19721974)hasstatisticallyestimatedthat705,215workersarepotentiallyexposedtooxalic
acidintheUSA(1).NIOSH(NOESSurvey19811983)hasstatisticallyestimatedthat130,128workersare
potentiallyexposedtooxalicacidintheUSA(2).
(1)NIOSHNationalOccupationalHazardSurvey(NOHS)(1974)(2)NIOSHNationalOccupationalExposureSurvey(NOES)
(1983)
fromHSDB
12.2.19 BodyBurdens
Oxalicacidcalciumsaltisamajorconstituentofkidneystones(1).
(1)BernalesCAetalKirkOthmerEncyclChemTech.3rdNY:Wiley16:61836(1981)
fromHSDB
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13 Literature
13.1 DepositorProvidedPubMedCitations
DepositorProvidedPubMed
Citations
3531records
fromPubChem
13.2 NLMCuratedPubMedCitations
CLICKTOLOAD...
fromPubChem
13.3 SynthesisReferences
GiuseppeMessina,GiovanniM.Sechi,LorenoLorenzoni,GiovanniChessa,"Methodofpreparationofoxalicacid
estersandamides."U.S.PatentUS4981963,issuedJuly,1971.
fromDrugBank
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14 Patents
14.1 DepositorSuppliedPatentIdentifiers
CLICKTOLOAD...
fromPubChem
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15 BiomolecularInteractionsandPathways
15.1 ProteinBound3DStructures
CLICKTOLOAD...
fromPubChem
15.2 BiosystemsandPathways
CLICKTOLOAD...
fromPubChem
15.3 DrugBankInteractions
DrugBankInteractions:1of3
Target
ProtooncogenetyrosineproteinkinaseSrc Moreinformation...
GeneralFunction
Involvedinproteinkinaseactivity
GeneName
SRC
GenBankGene
AL133293
GenBankProtein
10635153
1. OveringtonJP,AlLazikaniB,HopkinsAL:Howmanydrugtargetsare
there?NatRevDrugDiscov.2006Dec5(12):9936.Pubmed
2. ImmingP,SinningC,MeyerA:Drugs,theirtargetsandthenatureand
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References
numberofdrugtargets.NatRevDrugDiscov.2006Oct5(10):82134.
Pubmed
3. BermanHM,WestbrookJ,FengZ,GillilandG,BhatTN,WeissigH,
ShindyalovIN,BournePE:TheProteinDataBank.NucleicAcidsRes.
2000Jan128(1):23542.Pubmed
fromDrugBank
Transporter
Solutecarrierorganicaniontransporterfamilymember2B1
Action
inhibitor
GeneralFunction
Involvedinaniontransporteractivity
SpecificFunction
MediatestheNa(+)independenttransportoforganicanionssuchas
taurocholate,theprostaglandinsPGD2,PGE1,PGE2,leukotrieneC4,
thromboxaneB2andiloprost
GeneName
SLCO2B1
GenBankGene
AB026256
GenBankProtein
5006263
References
KobayashiD,NozawaT,ImaiK,NezuJ,TsujiA,TamaiI:Involvementof
humanorganicaniontransportingpolypeptideOATPB(SLC21A9)inpH
dependenttransportacrossintestinalapicalmembrane.JPharmacolExpTher.
2003Aug306(2):7038.Epub2003Apr30.Pubmed
fromDrugBank
Transporter
Solutecarrierfamily22member8
Action
substrate
GeneralFunction
Carbohydratetransportandmetabolism
SpecificFunction
Playsanimportantroleintheexcretion/detoxificationofendogenousand
exogenousorganicanions,especiallyfromthebrainandkidney.Involvedinthe
transportbasolateralofsteviol,fexofenadine.Transportsbenzylpenicillin
(PCG),estrone3sulfate(E1S),cimetidine(CMD),2,4dichloro
phenoxyacetate(2,4D),paminohippurate(PAH),acyclovir(ACV)and
ochratoxin(OTA)
GeneName
SLC22A8
GenBankGene
AF097491
GenBankProtein
4378059
References
RaceJE,GrasslSM,WilliamsWJ,HoltzmanEJ:Molecularcloningand
characterizationoftwonovelhumanrenalorganicaniontransporters(hOAT1
andhOAT3).BiochemBiophysResCommun.1999Feb16255(2):50814.
Pubmed
fromDrugBank
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16 BiologicalTestResults
16.1 BioAssayResults
CLICKTOLOAD...
fromPubChem
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17 Classification
17.1 Ontologies
17.1.1 MeSHTree
CLICKTOLOAD...
fromMeSH
17.1.2 ChEBIOntology
CLICKTOLOAD...
fromChEBI
17.1.3 GeneOntology:BiologicalProcess
CLICKTOLOAD...
fromGeneOntology
17.1.4 GeneOntology:MolecularFunction
CLICKTOLOAD...
fromGeneOntology
17.1.5 KEGG:Metabolite
CLICKTOLOAD...
fromKEGG
17.1.6 WIPOIPC
CLICKTOLOAD...
fromWIPO
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18 InformationSources
1. OXALICACIDfromHSDB1100http://toxnet.nlm.nih.gov/cgibin/sis/search/r?
dbs+hsdb:@term+@rn+@rel+144627
2. OxalicAcidfromDrugBankDB03902http://www.drugbank.ca/drugs/DB03902
3. OXALICACIDfromILOICSC0529http://www.ilo.org/dyn/icsc/showcard.display?p_card_id=0529
PeerReviewStatus:24.11.2009Validated
4. OxalicacidfromNIOSHPocketGuidenpgd0474http://www.cdc.gov/niosh/npg/npgd0474.html
5. OXALICACIDfromOSHAOccupationalChemicalDB270
http://www.osha.gov/chemicaldata/chemResult.html?RecNo=270
6. OxalicacidfromCAMEOChemicalsCBNOAA00000000008966
http://cameochemicals.noaa.gov/chemical/8966
7. EPAChemicalDataReport144627http://www.epa.gov/cdr/
8. DrugBankDB03902interaction#1http://www.drugbank.ca/drugs/DB03902#targets
9. DrugBankDB03902interaction#2http://www.drugbank.ca/drugs/DB03902#transporters
10. DrugBankDB03902interaction#3http://www.drugbank.ca/drugs/DB03902#transporters
11. oxalicacidfromNJDOHRTKHazardousSubstanceList1445
http://nj.gov/health/eoh/rtkweb/documents/fs/1445.pdf
NewJerseyDepartmentofHealth,RighttoKnowHazardousSubstanceList
12. ECHA2056343http://echa.europa.eu/
15. REGULATION(EC)No1272/20086070060081http://www.reach
compliance.eu/english/compliance/CLP/CLPInitialVersion.html
16. Wiki772http://en.wikipedia.org/wiki/Oxalic_acid
17. FDA/SPLIndexingdata9E7R5L6H31
http://www.fda.gov/ForIndustry/DataStandards/StructuredProductLabeling/ucm377913.htm
18. TheCambridgeStructuralDatabaseCCDC929767http://www.ccdc.cam.ac.uk/pages/Home.aspx
TheCambridgeStructuralDatabaseprovidesaccessto3Dstructuresofmoleculesdeterminedexperimentallyusingdiffraction
techniques.
techniques.
techniques.
techniques.
techniques.
23. OxalicacidfromNISTRIforMUBZPKHOEPUJKRUHFFFAOYSANhttp://www.nist.gov/srd/nist1a.cfm
24. OxalicacidfromNISTGCMSforMUBZPKHOEPUJKRUHFFFAOYSANhttp://www.nist.gov/srd/nist1a.cfm
25. PubChemhttp://pubchem.ncbi.nlm.nih.gov
DatadepositedinorcomputedbyPubChem
26. OxalicAcidfromMeSH68019815http://www.ncbi.nlm.nih.gov/mesh/68019815
27. MeSHTreefromMeSHDescTreehttp://www.nlm.nih.gov/mesh/meshhome.html
MeSH(MedicalSubjectHeadings)istheNLMcontrolledvocabularythesaurususedforindexingarticlesforPubMed.
28. ChEBIOntologyfromChEBIOBOhttp://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontology
TheChEBIOntologyisastructuredclassificationoftheentitiescontainedwithinChEBI.
29. MetabolitefromKEGGbr08001http://www.genome.jp/dbgetbin/www_bget?brite:br08001
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Compoundswithbiologicalroles
30. biologicalprocessfromGeneOntologyGO_ROOT_486550
http://amigo.geneontology.org/amigo/term/GO:0008150
TheGeneOntology(GO)http://www.geneontology.org/projectprovidesacontrolledvocabularyoftermsfordescribingthe
functionsofgeneproducts,andisdividedintothreedomains.Eachterminthebiologicalprocessesdomain,shownhere,
representsrecognizedseriesofevents,oracollectionofmoleculareventswithadefinedbeginningandend.Mutant
phenotypesoftenreflectdisruptionsinbiologicalprocesses.Thetermsbelowapplytothegene/proteintarget(s)testedby
theBioAssay.
31. molecularfunctionfromGeneOntologyGO_ROOT_486552
http://amigo.geneontology.org/amigo/term/GO:0003674
TheGeneOntology(GO)http://www.geneontology.org/projectprovidesacontrolledvocabularyoftermsfordescribingthe
functionsofgeneproducts,andisdividedintothreedomains.Eachterminthemolecularfunctionsdomain,shownhere,
representaprotein'sjobsorabilities.Thesemayincludetransportingthingsaround,bindingtothings,holdingthingstogether
andchangingonethingintoanother.Thisisdifferentfromthebiologicalprocessesthegeneproductisinvolvedin,which
involvemorethanoneactivity.Thetermsbelowapplytothegene/proteintarget(s)testedbytheBioAssay.
32. InternationalPatentClassification2015fromWIPOIPChttp://www.wipo.int/classifications/ipc/
TheWorldIntellectualPropertyOrganization(WIPO)InternationalPatentClassification(IPC)providesforahierarchical
systemoflanguageindependentsymbolsfortheclassificationofpatentsandutilitymodelsaccordingtothedifferentareasof
technologytowhichtheypertain.
33. ReducingAgentsfromMeSH68019163http://www.ncbi.nlm.nih.gov/mesh/68019163
34. NCBILinkOuthttp://www.ncbi.nlm.nih.gov/projects/linkout
LinkOutisaservicethatallowsonetolinkdirectlyfromNCBIdatabasestoawiderangeofinformationandservicesbeyond
NCBIsystems.
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PUBCHEM COMPOUND OXALICACID

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