(S)-2-O-Acetylmalic anhydride

CAS: 59025-03-5

Ref. 3D-FA17128

Product Information

• Name: (S)-2-O-Acetylmalic anhydride
• Synonyms: (3S)-3-(Acetyloxy)dihydro-2,5-furandione(-)-Acetoxysuccinic anhydride(S)-(-)-2-Acetoxysuccinic anhydride, 2,5-Dioxotetrahydrofuran-3-Yl Acetate, (3S)-2,5-dioxotetrahydrofuran-3-yl acetate
• CAS: 59025-03-5

Description

(S)-2-O-Acetylmalic anhydride is a lactam that is synthesized from deoxyvasicinone. It is synthesized by the dehydrative acetylation of anthranilic acid with acetic anhydride and pyridine in a one-pot reaction. The reaction mixture is heated to reflux for about 12 hours, followed by quenching with ice water. After the organic layer is separated, (S)-2-O-acetylmalic anhydride can be purified by crystallization. This compound has been shown to inhibit the growth of subincanadine A and B, which are intermediates in the biosynthesis of enediyne antitumor agents. (S)-2-O-Acetylmalic anhydride also inhibits chiral epoxide hydrolase, which converts epoxides into their corresponding diols.

• Brand: Biosynth

Chemical properties

• Molecular weight: 158.11 g/mol
• Formula: C₆H₆O₅
• Purity: Min. 95%
• InChI: InChI=1S/C6H6O5/c1-3(7)10-4-2-5(8)11-6(4)9/h4H,2H2,1H3/t4-/m0/s1
• InChI key: InChIKey=SSWJHSASZZAIAU-BYPYZUCNSA-N
• SMILES: CC(=O)O[C@H]1CC(=O)OC1=O