You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Toxin, Toxin Target Database.
Record Information
Version2.0
Creation Date2014-09-11 05:20:13 UTC
Update Date2014-12-24 20:26:58 UTC
Accession NumberT3D4872
Identification
Common NameTartaric acid
ClassSmall Molecule
DescriptionTartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine. It is added to other foods to give a sour taste, and is used as an antioxidant. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death. The minimum recorded fatal dose for a human is about 12 grams. In spite of that, it is included in many foods, especially sour-tasting sweets. As a food additive, tartaric acid is used as an antioxidant with E number E334, tartrates are other additives serving as antioxidants or emulsifiers. Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images. It is a useful raw material in organic chemistry for the synthesis of other chiral molecules. The naturally occurring form of the acid is L-(+)-tartaric acid or dextrotartaric acid. The mirror-image (enantiomeric) form, levotartaric acid or D-(-)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially. Tartarate is believed to play a role in inhibiting kidney stone formation. Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract -- primarily in the large instestine. Only about 15-20% of consumed tartaric acid is secreted in the urine unchanged.
Compound Type
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Industrial/Workplace Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
(+)-(2R,3R)-Tartaric acid
(+)-tartarate
(+)-tartaric acid
(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid
(2R,3R)-2,3-dihydroxybutanedioate
(2R,3R)-2,3-dihydroxybutanedioic acid
(2R,3R)-2,3-dihydroxysuccinic acid
(2R,3R)-2,3-tartaric acid
(2R,3R)-Tartarate
(2R,3R)-Tartaric acid
(R,R)-(+)-tartaric acid
(R,R)-tartarate
(R,R)-tartaric acid
(R,R)-tartrate
1,2-Dihydroxyethane-1,2-dicarboxylic acid
2,3-Dihydroxy-succinate
2,3-Dihydroxy-succinic acid
2,3-Dihydroxybutanedioate
2,3-Dihydroxybutanedioic acid
2,3-Dihydroxysuccinic acid
D-a,b-Dihydroxysuccinic acid
D-Tartaric acid
Dextrotartaric acid
L(+)-Tartaric acid
L-(+)-Tartaric acid
L-Tartarate
L-Tartaric acid
L-Threaric acid
Natural tartaric acid
Rechtsweinsaeure
TAR
Tartarate
Tartrate
Threaric acid
TLA
Weinsaeure
Chemical FormulaC4H6O6
Average Molecular Mass150.087 g/mol
Monoisotopic Mass150.016 g/mol
CAS Registry Number87-69-4
IUPAC Name(2R,3R)-2,3-dihydroxybutanedioic acid
Traditional NameL(+)-tartaric acid
SMILES[H][C@](O)(C(O)=O)[C@@]([H])(O)C(O)=O
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 KeyInChIKey=FEWJPZIEWOKRBE-JCYAYHJZSA-N
Chemical Taxonomy
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
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Sugar acid
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Fatty acid
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Platelet
  • Prostate
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point169 °C
Boiling PointNot Available
Solubility582 mg/mL at 20 °C
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility161.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.21 m3·mol-1ChemAxon
Polarizability11.33 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0930000000-19235937e21066a9c484View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-000f-0961000000-559c31b016f4fb3700d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0096-9200000000-df0ce9fba754b55674b1View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0007-0961000000-1b17d674621eb9d88c3cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0930000000-19235937e21066a9c484View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-000f-0961000000-559c31b016f4fb3700d2View 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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB00956
PubChem Compound ID444305
ChEMBL IDCHEMBL1236315
ChemSpider ID392277
KEGG IDC00898
UniProt IDNot Available
OMIM ID
ChEBI ID15671
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDTLA
ACToR IDNot Available
Wikipedia LinkTartaric acid
References
Synthesis ReferenceMilas, N. A.; Terry, Ethel M. Oxidation of fumaric and of maleic acids to tartaric acid. Journal of the American Chemical Society (1925), 47 1412-8.
MSDSLink
General References
  1. Petrarulo M, Marangella M, Bianco O, Linari F: Ion-chromatographic determination of L-tartrate in urine samples. Clin Chem. 1991 Jan;37(1):90-3. [1988215 ]
  2. Lord RS, Burdette CK, Bralley JA: Significance of urinary tartaric acid. Clin Chem. 2005 Mar;51(3):672-3. [15738524 ]
  3. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [19212411 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC503.51 uMNVS_NR_hPPARgNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]