Basic information
- Standard SMILES
O=C(O)[C@H](O)[C@@H](O)C(=O)O- InChIKey
FEWJPZIEWOKRBE-JCYAYHJZSA-N- Molecular formula
- C4H6O6
- Average molar mass
- 150.09 g/mol
- Monoisotopic mass
- 150.01643791
Names & identifiers
- Preferred name
- L-Tartaric acid
- IUPAC
- (2R,3R)-2,3-dihydroxybutanedioic acid
- English name
- DL-Tartaric acid
- Molecular formula
- C4H6O6
- Molecular weight
- 150.09
Names & synonyms
L-tartaric acid87-69-4L-(+)-Tartaric acidtartaric acid(2R,3R)-2,3-dihydroxysuccinic acid(2R,3R)-2,3-dihydroxybutanedioic acid(+)-Tartaric acid(+)-L-Tartaric acid(R,R)-Tartaric acidThrearic acidDextrotartaric acidL-threaric acid
Show more names
RACEMIC ACIDdl-Tartaric acid anhydrousDL-TARTRATEDL-TartaricClopidogrel Impurity 45DL-Tartaric acid concentrateButanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel-DL-Tartaric acid 133-37-9 pure 99% food additives Paratartaric acid kf-wang(at)kf-chem.comUvic acid
Natural tartaric acidAcidum tartaricum(+)-(R,R)-Tartaric acid(2R,3R)-Tartaric acidRechtsweinsaeureKyselina vinna(R,R)-(+)-Tartaric acidWeinsaeure
Database identifiers
- CAS
133-37-9、868-14-4、87-69-4- PubChem CID
- 444305
- DTXSID
DTXSID8023632- ChEMBL
CHEMBL1236315- ChEBI
CHEBI:15671- UNII
- 4J4Z8788N8、W4888I119H
- EC Number
- 201-766-0、205-105-7
- Nikkaji
- J31.839F
Properties
Computed structural properties
- XLogP
- -1.9
- Topological polar surface area
- 115 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 134
Physicochemical properties
- Melting point
- 210 · 210-212 °C(lit.)
- Boiling point
- 191.59 °C · 191.59°C (rough estimate)
- alpha
- 20 · [α]D20 -0.2～+0.2° (c=20, H2O)
- Density
- 1.788 · 1.788
- vapor pressure
- 0.1 hPa · <0.1 hPa (20 °C)
- FEMA
- 3044 · 3044 | TARTARIC ACID (D-, L-, DL-, MESO-)
- refractive index
- 1.586 · 1.5860 (estimate)
- FLAVIS Number
- 8.018 · 08.018 | Tartaric acid
- Flash point
- 210 °C · 210 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 2 O: · H2O: 0.1 g/mL, clear
- form
- Liquid
- pka
- 3.03 · 3.03, 4.37(at 25℃)
- color
- White
- PH
- 3.19 · 3.19(1 mM solution);2.58(10 mM solution);2.03(100 mM solution);
- Odor
- 100 % · at 100.00 %. very mild caramellic
- Odor Type
- odorless
- biological source
- synthetic
- Water Solubility
- soluble
- Merck
- 14 · 14,9069
- JECFA Number
- 621 · 621
- BRN
- 1725148 · 1725148
- Dielectric constant
- 35.9 · 35.9(-10℃)
- Stability
- Stable. Incompatible with bases, oxidizing agents, reducing agents, silver.
- Major Application
- 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
- -1.43 · -1.43
- CAS DataBase Reference
- 133 · 133-37-9(CAS DataBase Reference)
- FDA UNII
- 4 J4Z8788N8 · 4J4Z8788N8
- NIST Chemistry Reference
- Tartaric acid(133-37-9)
- EPA Substance Registry System
- 2 · Butanedioic acid, 2,3-dihydroxy-, (2R,3R)-rel- (133-37-9)
- UNSPSC Code
- 41116105 · 41116105
- NACRES
- 21 · NB.21
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 318 · H318
- Precautionary statements
- 280 · P280-P305+P351+P338+P310
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-41
- Safety Statements
- 26 · 26-37/39-36
- WGK Germany
- 3 · 3
- Autoignition Temperature
- 425 °C · 425 °C
- TSCA
- TSCA listed
- HS Code
- 29181200 · 29181200
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 1 · Eye Dam. 1
- REACH Registrations
- Active
Safety & regulation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29181200
- risk_code
- 36/37/38-41
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- safety_code
- 26-37/39-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H318
- REACH Registrations
- Active
- Hazard Classifications
- Eye Dam. 1
- Autoignition Temperature
- 425 °C
- Precautionary statements
- P280-P305+P351+P338+P310
Chemistry & industry
Applications
Occurrenced-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.
UsesDL-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 methods
PreparationThe 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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: DL-Tartaric acid is a tetraric acid that is butanedioic acid substituted by hydroxy groups at positions 2 and 3. It has a role as a human xenobiotic metabolite and a plant metabolite. It is a conjugate acid of a 3-carboxy-2,3-dihydroxypropanoate.
Related reactions
305 records
Linked notes
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