Record Information
Version1.0
Creation date2010-04-08 22:04:50 UTC
Update date2018-05-29 00:31:56 UTC
Primary IDFDB001112
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTartaric acid
DescriptionTartaric acid, also known as tartrate or (2R,3R)-tartarate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Tartaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Tartaric acid exists in all living organisms, ranging from bacteria to humans. Tartaric acid has been detected, but not quantified in, several different foods, such as tamarinds, coffee and coffee products, citrus, alcoholic beverages, and common grapes. This could make tartaric acid a potential biomarker for the consumption of these foods. Tartaric acid is a potentially toxic compound.
CAS Number133-37-9
Structure
Thumb
Synonyms
SynonymSource
(+)-(R,R)-Tartaric acidChEBI
(+)-L-Tartaric acidChEBI
(+)-Tartaric acidChEBI
(+)-WeinsaeureChEBI
(2R,3R)-2,3-DihydroxybernsteinsaeureChEBI
(2R,3R)-2,3-Dihydroxysuccinic acidChEBI
(2R,3R)-Tartaric acidChEBI
(R,R)-(+)-Tartaric acidChEBI
(R,R)-Tartaric acidChEBI
L(+)-TARTARIC ACIDChEBI
L-Threaric acidChEBI
RechtsweinsaeureChEBI
WeinsteinsaeureChEBI
(R,R)-TartrateKegg
L-Tartaric acidKegg
TartrateKegg
2,3-Dihydroxybutanedioic acidKegg
(+)-(R,R)-TartarateGenerator
(+)-L-TartarateGenerator
(+)-TartarateGenerator
(2R,3R)-2,3-DihydroxysuccinateGenerator
(2R,3R)-TartarateGenerator
(R,R)-(+)-TartarateGenerator
(R,R)-TartarateGenerator
L(+)-TARTARateGenerator
L-ThrearateGenerator
(R,R)-Tartric acidGenerator
L-TartarateGenerator
Tartric acidGenerator
2,3-DihydroxybutanedioateGenerator
TartarateGenerator
Aluminum tartrateHMDB
Ammonium tartrateHMDB
Potassium tartrateHMDB
Seignette saltHMDB
Sodium ammonium tartrateHMDB
Stannous tartrateHMDB
Tartaric acid, calcium salt, (R-r*,r*)-isomerHMDB
Calcium tartrate tetrahydrateHMDB
Sodium tartrateHMDB
Tartaric acid, ((r*,r*)-(+-))-isomerHMDB
Tartaric acid, monoammonium salt, (R-(r*,r*))-isomerHMDB
(R*,r*)-(+-)-2,3-dihydroxybutanedioic acid, monoammonium monosodium saltHMDB
MN(III) tartrateHMDB
Calcium tartrateHMDB
Tartaric acid, (R-(r*,r*))-isomerHMDB
Sodium potassium tartrateHMDB
Tartaric acid, (r*,s*)-isomerHMDB
Tartaric acid, (S-(r*,r*))-isomerHMDB
Tartaric acid, ammonium sodium salt, (1:1:1) salt, (r*,r*)-(+-)-isomerHMDB
(+)-(2R,3R)-Tartaric acidHMDB
(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acidHMDB
(2R,3R)-2,3-DihydroxybutanedioateHMDB
(2R,3R)-2,3-Dihydroxybutanedioic acidHMDB
(2R,3R)-2,3-Tartaric acidHMDB
1,2-Dihydroxyethane-1,2-dicarboxylic acidHMDB
2,3-Dihydroxy-succinateHMDB
2,3-Dihydroxy-succinic acidHMDB
2,3-Dihydroxysuccinic acidHMDB
D-a,b-Dihydroxysuccinic acidHMDB
D-Tartaric acidHMDB
Dextrotartaric acidHMDB
L-(+)-Tartaric acidHMDB
Natural tartaric acidHMDB
TARHMDB
Threaric acidHMDB
TLAHMDB
WeinsaeureHMDB
(2R,3R)-(+)-Tartaric acidHMDB
Dihydroxysuccinic acidHMDB
Tartaric acidHMDB
(2R,3R)-rel-2,3-dihydroxybutanedioic acidmanual
2,3-Dihydrosuccinic acidbiospider
2,3-dihydroxy-succinatebiospider
2,3-Dihydroxybutanedioic acid, 9CIdb_source
Butanedioic acid, 2,3-dihydroxy-biospider
DL-tartaric acidmanual
Malic acid, 3-hydroxy-biospider
Succinic acid, 2,3-dihydroxy-biospider
Predicted Properties
PropertyValueSource
Water Solubility161 g/LALOGPS
logP-1.3ALOGPS
logP-1.8ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.21 m³·mol⁻¹ChemAxon
Polarizability11.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H6O6
IUPAC name(2R,3R)-2,3-dihydroxybutanedioic acid
InChI IdentifierInChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1
InChI KeyFEWJPZIEWOKRBE-JCYAYHJZSA-N
Isomeric SMILESO[C@H]([C@@H](O)C(O)=O)C(O)=O
Average Molecular Weight150.0868
Monoisotopic Molecular Weight150.016437924
Classification
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Sugar acid
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Foods

Beverages:

Fruits and vegetables:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 32.01%; H 4.03%; O 63.96%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0930000000-19235937e21066a9c484View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-000f-0961000000-559c31b016f4fb3700d2View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-0961000000-1b17d674621eb9d88c3cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0930000000-19235937e21066a9c484View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000f-0961000000-559c31b016f4fb3700d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-9200000000-df0ce9fba754b55674b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000b-7900000000-d247ec12b77f427e9a76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-05fu-9000000000-4bf01ad116d24a453817View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-4da65da10f3a34f77688View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-ecb902731b9f6eb3764dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0072-9700000000-1e8e6f410c1d71af856eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-f13ad2560d3e6818db9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-05fu-9000000000-f46a01eb933ba6fbceacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-08dec35ca6a80add253aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-ecb902731b9f6eb3764dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0072-9700000000-1e8e6f410c1d71af856eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-f13ad2560d3e6818db9cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05fu-9000000000-f46a01eb933ba6fbceacView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-08dec35ca6a80add253aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-1900000000-6a73140cfa5a0c0234e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9600000000-ca8758d1e65f5dbe35d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-9100000000-1630b812321816f95d11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05bb-7900000000-146a1c7b189a7bbacda0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9500000000-f7af07684007cf14bdceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a8f5502da9e4d13e4144View in MoNA
MSMass Spectrum (Electron Ionization)splash10-056r-9000000000-16517a02beb9427ceaffView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID26849
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBTJ82-E:BTJ82-E
EAFUS IDNot Available
Dr. Duke IDTARTARIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1060791
SuperScent IDNot Available
Wikipedia IDTartaric_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
acidifier64047 Any substance which is added to food to preserve or enhance its flavour and/or appearance.DUKE
additive64047 Any substance which is added to food to preserve or enhance its flavour and/or appearance.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
irritantDUKE
sequestrant77963 A food preservative that acts by chelating with metal cations (particularly those of copper, iron and nickel) that catalyse the oxidation of fats in food.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
very mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramellic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).