51591-38-9

Basic information

• Product Name: (-)-DIACETYL-L-TARTARIC ACID
• Synonyms: (-)-DIACETYL-L-TARTARIC ACID;(R,R)-DIACETYLTARTARIC ACID;Diacetyltartaricacid;[R(R*,R*)]-2,3-bis(acetoxy)succinic acid;(-)-DIACETYL-L-TARTARIC ACID 98+%;(-)-2-O,3-O-Diacetyl-L-tartaric acid;(-)-Di-O-acetyl-L-tartaric acid;(+)-L-Tartaric acid 2,3-diacetate
• CAS NO: 51591-38-9
• Molecular Formula: C₈H₁₀O₈
• Molecular Weight: 234.16
• EINECS: 257-303-8
• Product Categories: Carboxylic Acids (Chiral);Chiral Building Blocks;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry
• Mol File: 51591-38-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 120°C
• Boiling Point: 398.9°Cat760mmHg
• Flash Point: 159.4°C
• Appearance: /
• Density: 1.486g/cm³
• Refractive Index: -25 ° (C=10, Acetone)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: almost transparency in Acetone
• PKA: 2.12±0.25(Predicted)
• CAS DataBase Reference: (-)-DIACETYL-L-TARTARIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-DIACETYL-L-TARTARIC ACID(51591-38-9)
• EPA Substance Registry System: (-)-DIACETYL-L-TARTARIC ACID(51591-38-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 51591-38-9(Hazardous Substances Data)

Usage

Uses

(-)-Diacetyl-L-tartaric Acid is a derivative of L-Tartaric Acid (T007630), which is a naturally occurring chemical compound found in berries, grapes and various wines, and provides antioxidant properties and contributes to the sour taste within these products. (-)-Diacetyl-L-tartaric Acid has been studied in relation to wheat, dough additives and properties as an emulsifier.

Upstream product

• 6283-74-5 (3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate 
• 87-69-4 L-Tartaric acid 
• 87-69-4 tartaric acid 
• 75-36-5 acetyl chloride 
• 7732-18-5 water 
• 122376-19-6 O²,O³-diacetyl-tartaric acid anhydride 

Downstream Products

• 64-19-7 acetic acid 
• 87-69-4 tartaric acid 
• 141-78-6 ethyl acetate 
• 117384-45-9 (4R,5R)-di-tert-butyl tartrate 

Relevant articles and documents

Hydroxycinnamoyl Glucose and Tartrate Esters and Their Role in the Formation of Ethylphenols in Wine

Synthesized p-coumaroyl and feruloyl l-tartrate esters were submitted to Brettanomyces bruxellensis strains AWRI 1499, AWRI 1608, and AWRI 1613 to assess their role as precursors to ethylphenols in wine. No evolution of ethylphenols was observed. Additionally, p-coumaroyl and feruloyl glucose were synthesized and submitted to B. bruxellensis AWRI 1499, which yielded both 4-ethylphenol and 4-ethylguaiacol. Unexpected chemical transformations of the hydroxycinnamoyl glucose esters during preparation were investigated to prevent these in subsequent synthetic attempts. Photoisomerization gave an isomeric mixture containing the trans-esters and undesired cis-esters, and acyl migration resulted in a mixture of the desired 1-O-β-ester and two additional migrated forms, the 2-O-α- and 6-O-α-esters. Theoretical studies indicated that the photoisomerization was facilitated by deprotonation of the phenol, and acyl migration is favored during acidic, nonaqueous handling. Preliminary LC-MS/MS studies observed the migrated hydroxycinnamoyl glucose esters in wine and allowed for identification of feruloyl glucose in red wine for the first time.