59025-03-5

Basic information

• Product Name: (-)-O-ACETYL-L-MALIC ANHYDRIDE
• Synonyms: 2-O-ACETYL-(S)-MALIC ANHYDRIDE;(-)-O-ACETYL-L-MALIC ANHYDRIDE;(S)-(-)-O-ACETYLMALIC ANHYDRIDE;(S)-(-)-2-ACETOXYSUCCINIC ANHYDRIDE;(S)-2-ACETOXYSUCCINIC ANHYDRIDE;2-acetoxysuccinicanhydride;L-O-Acetylmalic Anhydride;(s)-3-acetoxy-dihydro-2,5-furandione
• CAS NO: 59025-03-5
• Molecular Formula: C₆H₆O₅
• Molecular Weight: 158.11
• Product Categories: Chiral Reagents;Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Chiral Compound;Heterocycles;Miscellaneous Reagents
• Mol File: 59025-03-5.mol
• Article Data: 28

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: 296.588°C at 760 mmHg
• Flash Point: 133.093°C
• Appearance: /Powder
• Density: 1.386g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: -25.5 ° (C=5, CHCl3)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Dichloromethane, DMF, Ethyl Acetate
• Water Solubility: Reacts in water.
• Sensitive: Moisture Sensitive
• Stability: Stable. Incompatible with strong oxidizing agents. Sensitive to moisture.
• BRN: 82504
• CAS DataBase Reference: (-)-O-ACETYL-L-MALIC ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-O-ACETYL-L-MALIC ANHYDRIDE(59025-03-5)
• EPA Substance Registry System: (-)-O-ACETYL-L-MALIC ANHYDRIDE(59025-03-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 59025-03-5(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 59025-03-5 differently. You can refer to the following data:
1. (-)-O-Acetyl-L-Malic Anhydride can be used as intermediates for detergents via O-acetylmalic acid amides. Regioselective ring opening of malic acid anhydrides by carbon nucleophiles
2. (S)-(-)-2-Acetoxysuccinic anhydride is used as intermediates for detergents via O-acetylmalic acid amides. Regioselective ring opening of malic acid anhydrides by carbon nucleophiles.

Purification Methods

Recrystallise it from Ac2O and dry it in a vacuum over KOH, or by washing it with dry Et2O due to its deliquescent nature. [Jones J Chem Soc 788 1933, Henrot et al. Synth Commun 16 183 1986, Shiuey et al. J Org Chem 52 1040 1988, RS: Cohen et al. J Am Chem Soc 88 5306 1966.]

InChI:InChI=1/C6H6O5/c1-3(7)10-4-2-5(8)11-6(4)9/h4H,2H2,1H3/t4-/m0/s1

Upstream product

• 97-67-6 (S)-Malic acid 
• 108-24-7 acetic anhydride 
• 56-84-8 L-Aspartic acid 
• 75-36-5 acetyl chloride 
• 636-61-3 D-Malic acid 
• 1783-96-6 (2R)-aspartic acid 

Downstream Products

• 86534-22-7 (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione 
• 79778-86-2 (R)-3-acetoxy-3-benzyloxycarbonyl propionic acid 
• 620608-69-7 (3S)-1-{[6-(4-ethylphenoxy)pyridin-3-yl]methyl}-2,5-dioxopyrrolidin-3-yl acetate 
• 906802-36-6 (3R)-1-(2-(3,4-dimethoxyphenethoxy)cyclohexyl)-2,5-dioxopyrrolidin-3-yl acetate 
• 917979-64-7 (3R)-1-((1R,2R)-2-benzyloxycyclohex-1-yl)-2,5-dioxopyrrolidin-3-yl acetate 
• 146912-66-5 (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid 
• 129823-21-8 (S)-4-acetoxy-1-benzyl-2,5-pyrrolidinedione 
• 1360728-87-5 (3R)-1-(2-(3,4-dimethoxyphenethoxy)cyclohexyl)pyrrolidin-3-ol 
• 1202077-85-7 C₂₇H₂₂FN₃O₅S 
• 1202077-84-6 C₂₇H₂₂FN₃O₅S 
• 1360817-32-8 C₂₇H₂₂FN₃O₅S 
• 1360817-33-9 C₂₇H₂₂FN₃O₅S 
• 1044588-24-0 (3S)-1-[6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridin-4-yl]-2,5-dioxopyrrolidin-3-yl acetate 

Relevant articles and documents

A refining method of Venacaran hydrochloride

The present invention discloses a refining method of Venacaran hydrochloride; said method comprising preparation of Vinacarlan hydrochloride crude product and halogenated hydrocarbon washing, alkalinization, extraction, salting, recrystallization step, by the method of the present application, the peak time of about 32mins of unknown impurities ImpA may be completely removed, to obtain a quality superior to the preparation of the original Manufacturer Cadioomex Pharmaceutical Company of Wienakaran hydrochloride solids. The method is simple to operate, the conditions are mild, the requirements for the equipment are low, and the purity of the obtained Vinacarlan hydrochloride can reach more than 99.9%. At the same time, the method does not use heavy metals, which is conducive to the manufacture of Vi?akalan hydrochloride into injections.

Asymmetric synthesis of (S)-dihydrokavain from l-malic acid

A practical and efficient asymmetric synthesis of (S)-dihydrokavain from known ethyl (S)-2-hydroxy-4-phenylbutanoate which is, in turn, readily available from l-malic acid as a cheap chiral pool material is described using regioselective ring-opening of the 1,2-cyclic sulfate with lithium-3,3,3-triethoxypropiolate and subsequent HgO/H2SO4-mediated lactonization as the key steps. Its opposite enantiomer (R)-dihydrokavain was also synthesized from d-malic acid using the same sequences of reactions for the purpose of optical purity determination.

Preparation method of chromanone 2-carboxylic acid or chroman 2-carboxylic acid derivatives

The present invention relates to a chromanone-2-carboxylic acid derivative and a chroman-2-carboxylic acid derivative which can be used as an intermediate for effective medicinal components currently available in the market, and to preparation methods the