Basic information
- CAS
87-91-2- Standard SMILES
CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC- InChIKey
YSAVZVORKRDODB-PHDIDXHHSA-N- Molecular formula
- C8H14O6
- Average molar mass
- 206.19 g/mol
- Monoisotopic mass
- 206.07903817
Overview
diethyl tartrate is a metabolite found in or produced by Saccharomyces cerevisiae.
Names & identifiers
- Preferred name
- Diethyl tartrate
- IUPAC
- diethyl (2R,3R)-2,3-dihydroxybutanedioate
- English name
- L(+)-Diethyl L-tartrate
- Molecular formula
- C8H14O6
- Molecular weight
- 206.19
Names & synonyms
87-91-2Diethyl L-tartrateEthyl tartrateFEMA No. 2378DTXSID5052597Diethyl (+)-tartrateOQ72CPY58ZDiethyl 1,2-dihydroxy-1,2-ethanedicarboxylateTartaric acid, diethyl esterDTXCID6031170NSC-44808BUTANEDIOIC ACID, 2,3-DIHYDROXY-(R-(R*,R*))-, DIETHYL ESTER
Show more names
DETL-DETFEMA 2378Diethyl (2R,3R)-tartratediethyl tartarate(+)-Diethyl L-tartrate(2S,3S)-diethyl 2,3-dihydroxysuccinateDiethyl (2R,3R)-2,3-dihydroxybutanedioate
RefChem:133449Tartaric acid diethyl esterBUTANEDIOIC ACID, 2,3-DIHYDROXY-(2R,3R)-, DIETHYL ESTERBUTANEDIOIC ACID, 2,3-DIHYDROXY-(2R,3R)-, 1,4-DIETHYL ESTER201-783-3Diethyl 2,3-dihydroxysuccinateDiethyl tartrate(2R,3R)-Diethyl 2,3-dihydroxysuccinate
Database identifiers
- CAS
87-91-2- PubChem CID
- 6993580
- DTXSID
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 93.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 180
Experimental & physicochemical properties
FragrancesFragrance Ingredient (Diethyl tartrate) -> IFRA transparency List
LogP-0.29
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
1.203-1.210 (20 °C)
1.24 @25 °C
Flavoring AgentsEU Flavoring substances
Solubility
slightly soluble to insoluble in water; miscible in oil and alcohol
(in ethanol)
Boiling Point
280-281 °C; 153 °C (12 mm Hg)
280 °C @760 [mm Hg]
Refractive Index1.443-1.449
Physical Descriptioncolourless viscous liquid with very faint winey odour
Physicochemical properties
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 99.8% (1418 of 1421) of all reports.
Not Classified
Aggregated GHS information provided per 1421 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Butanedioic acid, 2,3-dihydroxy- [R-(R*,R*)]-, diethyl ester
Status: Active Update: 10-11-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18416
Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, diethyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesNot Classified
Safety & protection
Protective Action Criteria (PAC)
30 [mg/m3]
330 [mg/m3]
2000 [mg/m3]
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29181300
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24/25-36-26
- Storage Class
- 10 - Combustible liquids
Chemistry & industry
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENTFood Additives -> CARRIER_SOLVENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENTFood Additives -> CARRIER_SOLVENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENTFood Additives -> CARRIER_SOLVENT -> JECFA Functional Classes
General Manufacturing InformationButanedioic acid, 2,3-dihydroxy- (2R,3R)-, 1,4-diethyl ester: ACTIVE
Applications
OccurrenceThe d-isomer has not been reported found in nature; the l-isomer and the racemic form are of little importance. Reported found in sherry, white and red wine.
Uses(+)-Diethyl L-tartrate is used as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, for Sharpless-type enantioselective oxidation of sulfides to sulfoxides and as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction. It is also used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke therapy.
Uses(+)-Diethyl L-tartrate can be used in the synthesis of biologically active compounds such as (+)-altholactone, (-)-aspicilin, (+)-monomorine I and (+)-(1R,2R,3S,6S)-3,6-di-O-methyl conduritol-E.
UsesDiethyl L-(+)-Tartrate is used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke thera py.
General DescriptionMade from natural tartaric acid
Upstream & downstream products
Upstream raw materials
Related reactions
40 records
Compound notes
Loading…