Record Information
Version2.0
Creation Date2012-05-31 13:02:24 -0600
Update Date2015-09-13 12:56:09 -0600
Secondary Accession Numbers
  • ECMDB00956
Identification
Name:Tartaric acid
DescriptionTartaric acid is a white crystalline organic acid. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. 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. (Wikipedia) In E. coli K-12, tartaric acid is involved in glyoxylate and dicarboxylate metabolism. (KEGG)
Structure
Thumb
Synonyms:
  • (+)-(2R,3R)-Tartarate
  • (+)-(2R,3R)-Tartaric acid
  • (+)-tartarate
  • (+)-tartaric acid
  • (+)-tartrate
  • (+)-tartric acid
  • (1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylate
  • (1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid
  • (2R,3R)-2,3-dihydroxybutanedioate
  • (2R,3R)-2,3-dihydroxybutanedioic acid
  • (2R,3R)-2,3-dihydroxysuccinate
  • (2R,3R)-2,3-dihydroxysuccinic acid
  • (2R,3R)-2,3-tartarate
  • (2R,3R)-2,3-tartaric acid
  • (2R,3R)-Tartarate
  • (2R,3R)-Tartaric acid
  • (2R,3R)-tartrate
  • (2R,3R)-tartric acid
  • (R,R)-(+)-tartarate
  • (R,R)-(+)-tartaric acid
  • (R,R)-tartarate
  • (R,R)-tartaric acid
  • (R,R)-tartrate
  • (R,R)-tartric acid
  • 1,2-Dihydroxyethane-1,2-dicarboxylate
  • 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-Dihydroxysuccinate
  • 2,3-Dihydroxysuccinic acid
  • D-a,b-Dihydroxysuccinate
  • D-a,b-Dihydroxysuccinic acid
  • D-Tartarate
  • D-Tartaric acid
  • Dextrotartarate
  • Dextrotartaric acid
  • L(+)-Tartarate
  • L(+)-Tartaric acid
  • L-(+)-Tartarate
  • L-(+)-Tartaric acid
  • L-Tartarate
  • L-Tartaric acid
  • L-Threarate
  • L-Threaric acid
  • Natural tartarate
  • Natural tartaric acid
  • Rechtsweinsaeure
  • TAR
  • Tartarate
  • Tartaric acid
  • Tartrate
  • Tartric acid
  • Threarate
  • Threaric acid
  • TLA
  • Weinsaeure
Chemical Formula:C4H6O6
Weight:Average: 150.0868
Monoisotopic: 150.016437924
InChI Key:FEWJPZIEWOKRBE-JCYAYHJZSA-N
InChI:InChI=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
CAS number:87-69-4
IUPAC Name:(2R,3R)-2,3-dihydroxybutanedioic acid
Traditional IUPAC Name:L(+)-tartaric acid
SMILES:O[C@H]([C@@H](O)C(O)=O)C(O)=O
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
  • 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
Physical Properties
State:Solid
Charge:-2
Melting point:169 °C
Experimental Properties:
PropertyValueSource
Water Solubility:582 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
glycolate and glyoxylate degradation IIPW002021 ThumbThumb?image type=greyscaleThumb?image type=simple
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not 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
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Lord RS, Burdette CK, Bralley JA: Significance of urinary tartaric acid. Clin Chem. 2005 Mar;51(3):672-3. Pubmed: 15738524
  • 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. Pubmed: 1988215
  • 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. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Milas, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15671
HMDB IDHMDB00956
Pubchem Compound ID444305
Kegg IDC00898
ChemSpider ID392277
WikipediaTartaric acid
BioCyc IDTARTRATE
EcoCyc IDTARTRATE
Ligand ExpoTLA

Enzymes

General function:
Involved in lyase activity
Specific function:
(R,R)-tartrate = oxaloacetate + H(2)O
Gene Name:
ttdA
Uniprot ID:
P05847
Molecular weight:
32733
Reactions
(R,R)-tartrate = oxaloacetate + H(2)O.
General function:
Involved in hydro-lyase activity
Specific function:
(R,R)-tartrate = oxaloacetate + H(2)O
Gene Name:
ttdB
Uniprot ID:
P0AC35
Molecular weight:
22679
Reactions
(R,R)-tartrate = oxaloacetate + H(2)O.
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the NAD(+)-dependent oxidative decarboxylation of D-malate into pyruvate. Is essential for aerobic growth on D- malate as the sole carbon source. But is not required for anaerobic D-malate utilization, although DmlA is expressed and active in those conditions. Appears to be not able to use L- tartrate as a substrate for dehydrogenation instead of D-malate
Gene Name:
dmlA
Uniprot ID:
P76251
Molecular weight:
40315
Reactions
(R)-malate + NAD(+) = pyruvate + CO(2) + NADH.

Transporters

General function:
Involved in transporter activity
Specific function:
Catalyzes the uptake of tartrate in exchange for intracellular succinate. Essential for anaerobic L-tartrate fermentation
Gene Name:
ttdT
Uniprot ID:
P39414
Molecular weight:
52906
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368