L-Tartaric acid
TARTARIC ACID · RACEMIC ACID · dl-Tartaric acid anhydrous · DL-TARTRATE · DL-Tartaric · Clopidogrel Impurity 45 · DL-Tartaric acid concentrate · Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-
Identifiers & Physical Properties
| CAS No. | 133-37-9 |
|---|---|
| Molecular formula | C4H6O6 |
| Average molar mass | 150.09 g/mol |
| Monoisotopic mass | 150.01643791 g/mol |
| SMILES | O=C(O)[C@H](O)[C@@H](O)C(=O)O |
| InChIKey | FEWJPZIEWOKRBE-JCYAYHJZSA-N |
| PubChem CID | 444305 |
| ChEMBL | CHEMBL1236315 |
| ChEBI | CHEBI:15671 |
| EC No. | 201-766-0 |
| DTXSID | DTXSID8023632 |
Chemical & Physical Properties
| XLogP | -1.9 |
|---|---|
| Topological polar surface area | 115 |
| Hydrogen bond donors | 4 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 3 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 134 |
| Melting point | 210-212 °C(lit.) |
| Boiling point | 191.59°C (rough estimate) |
| alpha | [α]D20 -0.2～+0.2° (c=20, H2O) |
| Density | 1.788 |
| Vapor pressure | <0.1 hPa (20 °C) |
| FEMA | 3044 | TARTARIC ACID (D-, L-, DL-, MESO-) |
| Refractive index | 1.5860 (estimate) |
| FLAVIS Number | 08.018 | Tartaric acid |
| Flash point | 210 °C |
| Storage conditions | Store below +30°C. |
| Solubility | H2O: 0.1 g/mL, clearsoluble |
| Physical state | Liquid |
| pKa (acidity coefficient) | 3.03, 4.37(at 25℃) |
| Color | White |
| pH | 3.19(1 mM solution)2.58(10 mM solution)2.03(100 mM solution) |
| Odor | at 100.00 %. very mild caramellic |
| Odor type | odorless |
| Biological source | synthetic |
| Merck | 14,9069 |
| JECFA Number | 621 |
| BRN | 1725148 |
| Dielectric constant | 35.9(-10℃) |
| Stability | Stable. Incompatible with bases, oxidizing agents, reducing agents, silver. |
| Major applications | flavors and fragrances |
| Cosmetics Ingredients Functions | BUFFERINGFRAGRANCE |
| 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-/m0/s1 |
| InChIKey | FEWJPZIEWOKRBE-UHFFFAOYSA-N |
| SMILES | O[C@@H]([C@H](O)C(O)=O)C(O)=O |
| LogP (partition coefficient) | -1.43 |
| CAS DataBase Reference | 133-37-9(CAS DataBase Reference) |
| FDA UNII | 4J4Z8788N8 |
| NIST Chemistry Reference | Tartaric acid(133-37-9) |
| EPA Substance Registry System | Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel- (133-37-9) |
| UNSPSC Code | 41116105 |
| NACRES | NB.21 |
| GHS pictogram | GHS05 |
| Signal word | Danger |
| GHS hazard statements | H318 |
| GHS precautionary statements | P280-P305+P351+P338+P310 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38-41 |
| Safety statements (S) | 26-37/39-36 |
| Water hazard class (WGK) | 3 |
| Autoignition temperature | 425 °C |
| TSCA inventory status | TSCA listed |
| Customs code | 29181200 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Dam. 1 |
| REACH registrations | Active |
Safety & Regulations
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29181200 |
| Risk statements (R) | 36/37/38-41 |
| Signal word | Danger |
| GHS pictogram | GHS05 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-37/39-36 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H318 |
| REACH registrations | Active |
| Hazard class | Eye Dam. 1 |
| Autoignition temperature | 425 °C |
| GHS precautionary statements | P280-P305+P351+P338+P310 |
Applications & Uses
Occurrence
d-Tartaric acid occurs in many fruits or other parts of the plant, free or combined with potassium, calcium or magnesium. It is also reported found in raw, lean fish, white wine, red wine and port wine.
Uses
DL-Tartaric acid is used as a synergist for antioxidants, emulsifier, sequestrant and flavoring agent. It is also added with citric acid to prepare effervescent salts, thereby enhancing the taste of oral medications. It is also utilized in pigments, processing aids, ink, toner and colorant products. It acts as a chelating agent in metal and farming industries. Further, it is used as lubricant and grease. It is mixed with sodium bicarbonate and used as a leavening agent in food preparation. In the pharmaceutical industry, it is utilized in the preparation of tartar emetic, which is used in cough syrup as an expectorant.
Preparation & Synthesis
Preparation
The tartrates used in commerce are obtained as a by-product of wine manufacture and have the L(+) configuration. Produced from argols or wine lees, which are formed in the manufacture of wine by extracting the potassium acid tartrate, transforming this into the calcium salt and then acidifying with dilute sulfuric acid; also by oxidation of d-glucose with nitric acid. The dl-tartaric acid is obtained by boiling the d-tartaric acid with an aqueous solution of NaOH or by oxidation of fumaric acid. The l- and the meso-tartaric acid are also known, but are less important.