4701-54-6

Basic information

• Product Name: 16-O-deacetylfusidic acid lactone
• Synonyms: 16-O-deacetylfusidic acid lactone
• CAS NO: 4701-54-6
• Molecular Formula: C₂₉H₄₄O₄
• Molecular Weight: 456.67
• Mol File: 4701-54-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 602.2°Cat760mmHg
• Flash Point: 193.2°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 5.17E-17mmHg at 25°C
• Refractive Index: 1.564
• PKA: 14.69±0.70(Predicted)
• CAS DataBase Reference: 16-O-deacetylfusidic acid lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 16-O-deacetylfusidic acid lactone(4701-54-6)
• EPA Substance Registry System: 16-O-deacetylfusidic acid lactone(4701-54-6)

Safety Data

• Hazardous Substances Data: 4701-54-6(Hazardous Substances Data)

Usage

Uses

16-Deacetylfusidic Acid γ-Lactone is a metabolite of the drug Fusidic Acid (F865500). Fusidic acid is a bacteriostatic antibiotic. Fusidic Acid suppresses nitric oxide lysis of pancreatic islet cells. Inhibits protein synthesis in prokaryotes by inhibiting the ribosome-dependent activity of G factor and translocation of peptidyl-tRNA.

InChI:InChI=1/C29H44O4/c1-15(2)8-7-9-18-24-17(4)26(33-27(18)32)29(6)20-11-10-19-16(3)22(30)12-13-28(19,5)25(20)23(31)14-21(24)29/h8,16-17,19-23,25-26,30-31H,7,9-14H2,1-6H3/t16-,17?,19?,20-,21-,22+,23+,25-,26?,28-,29+/m0/s1

Upstream product

• 3482-49-3 fusidine 

Downstream Products

• 4701-60-4 17S,20R-dihydrofusidic acid lactone 
• 368859-51-2 3-O-TBDMS-21-O-diphenylmethylsilyl-16β-acetoxy-17S,20R-dihydrofusidin-3,11,16,21-tetrol 
• 335106-46-2 3-O-TBDMS-21-O-diphenylmethylsilyl-16β-acetoxy-17S,20S-dihydrofusidin-3,11,16,21-tetrol 
• 368859-50-1 3-O-TBDMS-21-O-diphenylmethylsilyl-17S,20R-dihydrofusidin-3,11,16,21-tetrol 
• 335106-44-0 3-O-TBDMS-21-O-diphenylmethylsilyl-17S,20S-dihydrofusidin-3,11,16,21-tetrol 
• 335106-26-8 17S,20S-dihydrofusidic acid lactone 
• 457889-92-8 C₅₁H₇₈O₅Si₂ 
• 457889-95-1 C₄₉H₇₆O₄Si₂ 

Relevant articles and documents

Synthesis and Biological Activity of Cyanoethyl Derivatives of Fusidic Acid

3,11-Dihydroxy and 3,11-dioxo triterpenoids of the fusidane series reacted with acrylonitrile in 1,4-dioxane in the presence of alkali and phase-transfer catalyst to give mono- and bis(2-cyanoethoxy) and 2-cyanoethyl derivatives. The reaction with 3,11-dioxo analog afforded 2,2-disubstituted derivative as a result of addition of two cyanoethyl groups to the α-position with respect to the C3=O carbonyl group. The isolated compounds were screened for antibacterial and antifungal activities.

17S,20S-Methanofusidic acid, a new potent semi-synthetic fusidane antibiotic.

A novel fusidic acid type antibiotic having the side chain linked to the tetracyclic ring system via a spiro-cyclopropane system is described. 17S,20S-Methanofusidic acid is obtained by an efficient synthetic route including cyclopropanation of the Delta17(20) bond with attack solely from the least hindered alpha-face. The spiro-cyclopropane system orients the side chain into a bioactive conformational space. The new 17S,20S-methanofusidic acid exerts antibacterial activity against several Gram-positive species with potency essentially equal to natural fusidic acid.