Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2022-02-17 19:22:55 UTC |
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NP-MRD ID | NP0000713 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Tartaric acid |
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Description | Tartaric 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 ). |
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Structure | O[C@H]([C@@H](O)C(O)=O)C(O)=O 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 |
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Synonyms | Value | Source |
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(+)-(R,R)-Tartaric acid | ChEBI | (+)-L-Tartaric acid | ChEBI | (+)-Tartaric acid | ChEBI | (+)-Weinsaeure | ChEBI | (2R,3R)-2,3-Dihydroxybernsteinsaeure | ChEBI | (2R,3R)-2,3-Dihydroxysuccinic acid | ChEBI | (2R,3R)-Tartaric acid | ChEBI | (R,R)-(+)-Tartaric acid | ChEBI | (R,R)-Tartaric acid | ChEBI | L(+)-TARTARIC ACID | ChEBI | L-Threaric acid | ChEBI | Rechtsweinsaeure | ChEBI | Weinsteinsaeure | ChEBI | (R,R)-Tartrate | Kegg | L-Tartaric acid | Kegg | Tartrate | Kegg | 2,3-Dihydroxybutanedioic acid | Kegg | (+)-(R,R)-Tartarate | Generator | (+)-L-Tartarate | Generator | (+)-Tartarate | Generator | (2R,3R)-2,3-Dihydroxysuccinate | Generator | (2R,3R)-Tartarate | Generator | (R,R)-(+)-Tartarate | Generator | (R,R)-Tartarate | Generator | L(+)-TARTARate | Generator | L-Threarate | Generator | (R,R)-Tartric acid | Generator | L-Tartarate | Generator | Tartric acid | Generator | 2,3-Dihydroxybutanedioate | Generator | Tartarate | Generator | Aluminum tartrate | HMDB | Ammonium tartrate | HMDB | Potassium tartrate | HMDB | Seignette salt | HMDB | Sodium ammonium tartrate | HMDB | Stannous tartrate | HMDB | Tartaric acid, calcium salt, (R-r*,r*)-isomer | HMDB | Calcium tartrate tetrahydrate | HMDB | Sodium tartrate | HMDB | Tartaric acid, ((r*,r*)-(+-))-isomer | HMDB | Tartaric acid, monoammonium salt, (R-(r*,r*))-isomer | HMDB | (R*,r*)-(+-)-2,3-dihydroxybutanedioic acid, monoammonium monosodium salt | HMDB | MN(III) tartrate | HMDB | Calcium tartrate | HMDB | Tartaric acid, (R-(r*,r*))-isomer | HMDB | Sodium potassium tartrate | HMDB | Tartaric acid, (r*,s*)-isomer | HMDB | Tartaric acid, (S-(r*,r*))-isomer | HMDB | Tartaric acid, ammonium sodium salt, (1:1:1) salt, (r*,r*)-(+-)-isomer | HMDB | (+)-(2R,3R)-Tartaric acid | HMDB | (1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid | HMDB | (2R,3R)-2,3-Dihydroxybutanedioate | HMDB | (2R,3R)-2,3-Dihydroxybutanedioic acid | HMDB | (2R,3R)-2,3-Tartaric acid | HMDB | 1,2-Dihydroxyethane-1,2-dicarboxylic acid | HMDB | 2,3-Dihydroxy-succinate | HMDB | 2,3-Dihydroxy-succinic acid | HMDB | 2,3-Dihydroxysuccinic acid | HMDB | D-a,b-Dihydroxysuccinic acid | HMDB | D-Tartaric acid | HMDB | Dextrotartaric acid | HMDB | L-(+)-Tartaric acid | HMDB | Natural tartaric acid | HMDB | TAR | HMDB | Threaric acid | HMDB | TLA | HMDB | Weinsaeure | HMDB | (2R,3R)-(+)-Tartaric acid | HMDB | Dihydroxysuccinic acid | HMDB | Tartaric acid | HMDB |
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Chemical Formula | C4H6O6 |
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Average Mass | 150.0868 Da |
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Monoisotopic Mass | 150.01644 Da |
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IUPAC Name | (2R,3R)-2,3-dihydroxybutanedioic acid |
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Traditional Name | L(+)-tartaric acid |
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CAS Registry Number | 87-69-4 |
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SMILES | O[C@H]([C@@H](O)C(O)=O)C(O)=O |
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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 |
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InChI Key | FEWJPZIEWOKRBE-JCYAYHJZSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-02-17 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Sugar acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | |
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Predicted Properties | |
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General References | - 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 ]
- Lord RS, Burdette CK, Bralley JA: Significance of urinary tartaric acid. Clin Chem. 2005 Mar;51(3):672-3. [PubMed:15738524 ]
- 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 ]
- 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 ]
- 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 ]
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