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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-17 19:22:55 UTC
NP-MRD IDNP0000713
Secondary Accession NumbersNone
Natural Product Identification
Common NameTartaric acid
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. Tartaric acid is a biomarker for the consumption of wine and grapes (PMID: 24507823 ). Tartaric acid is also a fungal metabolite, elevated levels in the urine (especially in children) may be due to the presence of yeast (in the gut or bladder). It can be produced by Agrobacterium, Nocardia, Rhizobium, Saccharomyces as well (PMID: 7628083 ) (Https://Link.Springer.Com/article/10.1023/A:1005592104426). High levels of tartaric acid have been found in autistic children. In adults, tartaric acid may be due to the consumption of wine (https://Www.Greatplainslaboratory.Com/articles-1/2015/11/13/candida-and-overgrowth-the-problem-bacteria-by-products) (PMID: 15738524 ; PMID: 24507823 ; PMID: 7628083 ).
Structure
Thumb
Synonyms
ValueSource
(+)-(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
Chemical FormulaC4H6O6
Average Mass150.0868 Da
Monoisotopic Mass150.01644 Da
IUPAC Name(2R,3R)-2,3-dihydroxybutanedioic acid
Traditional NameL(+)-tartaric acid
CAS Registry Number87-69-4
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O
InChI Identifier
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
InChI KeyFEWJPZIEWOKRBE-JCYAYHJZSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-17View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-17View Spectrum
Species
Species of Origin
Species NameSourceReference
Allium cepaFooDB
Annona squamosaFooDB
Apium graveolensFooDB
Avena sativa L.FooDB
Averrhoa carambolaKNApSAcK Database
Capparis spinosaFooDB
Carica papaya L.FooDB
Cichorium intybusFooDB
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Cydonia oblongaFooDB
Daucus carotaFooDB
Daucus carota ssp. sativusFooDB
Ficus caricaFooDB
Foeniculum vulgareFooDB
Helianthus annuus L.FooDB
Hibiscus sabbariffaFooDB
Lactuca sativaFooDB
Mangifera indicaKNApSAcK Database
Morus indicaKNApSAcK Database
Musa x paradisiacaFooDB
Pelargonium spp.KNApSAcK Database
Persea americanaFooDB
Petroselinum crispumFooDB
Prunus armeniacaFooDB
Prunus cerasusFooDB
Prunus domesticaFooDB
Punica granatumKNApSAcK Database
Ribes rubrumFooDB
Ribes uva-crispaFooDB
Rumex acetosaFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum tuberosumFooDB
Tamarindus indicaKNApSAcK Database
Taraxacum officinaleFooDB
Theobroma cacaoFooDB
Vitis viniferaKNApSAcK Database
Vitis vinifera L.FooDB
Xiphidium caeruleumKNApSAcK Database
Zea mays L.FooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point169 °CNot Available
Boiling Point399.26 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility582 mg/mL at 20 °CNot Available
LogP-1.426 (est)The Good Scents Company Information System
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000956
DrugBank IDDB09459
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001112
KNApSAcK IDC00001206
Chemspider ID392277
KEGG Compound IDC00898
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTartaric acid
METLIN IDNot Available
PubChem Compound444305
PDB IDNot Available
ChEBI ID15671
Good Scents IDrw1034811
References
General References
  1. 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. [PubMed:19212411 ]
  2. 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 ]
  3. Lord RS, Burdette CK, Bralley JA: Significance of urinary tartaric acid. Clin Chem. 2005 Mar;51(3):672-3. [PubMed:15738524 ]
  4. Shaw W, Kassen E, Chaves E: Increased urinary excretion of analogs of Krebs cycle metabolites and arabinose in two brothers with autistic features. Clin Chem. 1995 Aug;41(8 Pt 1):1094-104. [PubMed:7628083 ]
  5. Regueiro J, Vallverdu-Queralt A, Simal-Gandara J, Estruch R, Lamuela-Raventos RM: Urinary tartaric acid as a potential biomarker for the dietary assessment of moderate wine consumption: a randomised controlled trial. Br J Nutr. 2014 May;111(9):1680-5. doi: 10.1017/S0007114513004108. Epub 2014 Feb 10. [PubMed:24507823 ]
  6. Fu B, Shen Q, Qian W, Zeng Y, Sun X, Hannig M: Interfacial interaction of tartaric acid with hydroxyapatite and enamel. J Mater Sci Mater Med. 2005 Sep;16(9):827-31. doi: 10.1007/s10856-005-3581-6. [PubMed:16167111 ]