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

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

Uses

Used in Detergent Industry:
(-)-O-Acetyl-L-malic Anhydride is used as an intermediate for the production of detergents via O-acetylmalic acid amides. Its role in this application is due to its ability to undergo regioselective ring opening by carbon nucleophiles, which is a crucial step in the synthesis of certain detergent components.
Additionally, (S)-(-)-2-Acetoxysuccinic anhydride, a related compound, is also used as an intermediate for detergents through a similar process involving O-acetylmalic acid amides and regioselective ring opening by carbon nucleophiles. This highlights the versatility of these compounds in the detergent industry.

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 
• 636-61-3 D-Malic acid 
• 75-36-5 acetyl chloride 
• 1783-96-6 (2R)-aspartic acid 
• 56-84-8 L-Aspartic acid 

Downstream Products

• 174874-82-9 acetic acid (3S)-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl ester 
• 174874-81-8 acetic acid (3S)-1-(3,4-dimethoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl ester 
• 79778-86-2 (R)-3-acetoxy-3-benzyloxycarbonyl propionic acid 
• 906802-36-6 (3R)-1-(2-(3,4-dimethoxyphenethoxy)cyclohexyl)-2,5-dioxopyrrolidin-3-yl acetate 
• 1360728-87-5 (3R)-1-(2-(3,4-dimethoxyphenethoxy)cyclohexyl)pyrrolidin-3-ol 
• 1360817-32-8 C₂₇H₂₂FN₃O₅S 
• 1360817-33-9 C₂₇H₂₂FN₃O₅S 
• 917979-64-7 (3R)-1-((1R,2R)-2-benzyloxycyclohex-1-yl)-2,5-dioxopyrrolidin-3-yl acetate 
• 188540-85-4 (R)-2-acetoxy-4-oxo-4-phenylbutyric acid 
• 86534-23-8 1(S)-acetoxy-6(R)-(2-formyloxyprop-2-yl)-7(S)-<(benzyloxy)methyl>-7a(R)-hexahydro-3H-pyrrolizin-3-one 
• 86534-22-7 (+)-4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3-(E)-en-1-yl>-2,5-pyrrolidinedione 
• 86545-49-5 4(R)-acetoxy-1-<5-(benzyloxy)-2,2-dimethylpent-3(E)-en-1yl>-5-hydroxy-2-pyrrolidinone 
• 86534-24-9 (+)-1(S)-acetoxy-7(S)-<(benzyloxy)methyl>-6(R)-(2-hydroxyprop-2-yl)-7a(R)-hexahydro-3H-pyrrolizin-3-one 
• 636-61-3 D-Malic acid 

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Provided are indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which LRRK2 kinase is involved. Also provided are pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which LRRK2 kinase is involved.

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The present invention is directed to indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which the LRRK2 kinase is involved, such as Parkinson's Disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which LRRK-2 kinase is involved.

COMPOUNDS INHIBITING LEUCINE-RICH REPEAT KINASE ENZYME ACTIVITY

Disclosed are indazole compounds which are potent inhibitors of LRRK2 kinase and useful in the treatment or prevention of diseases in which LRRK2 kinase is involved. Also disclosed are pharmaceutical compositions in the prevention or treatment of such diseases in which LRRK2 kinase is involved.