Pleuromutilin
Title: Pleuromutilin
CAS Registry Number: 125-65-5
CAS Name: Hydroxyacetic acid (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester
Additional Names: glycolic acid 8-ester with octahydro-5,8-dihydroxy-4,6,9,10-tetramethyl-6-vinyl-3a,9-propano-3aH-cyclopentacycloocten-1(4H)-one; drosophilin B
Manufacturers' Codes: BC-757
Molecular Formula: C22H34O5
Molecular Weight: 378.50
Percent Composition: C 69.81%, H 9.05%, O 21.14%
Literature References: Antibiotic substance produced by the basidiomycetes Pleurotus mutilus (Fr.) Sacc. and P. passeckerianus Pilat.: Kavanagh et al., Proc. Natl. Acad. Sci. USA 37, 570 (1951); 38, 555 (1952). Isoln procedure: Anchel, J. Biol. Chem. 199, 133 (1952). Structure: D. Arigoni, Gazz. Chim. Ital. 92, 884 (1962); A. J. Birch et al., Chem. Ind. (London) 1963, 374; Tetrahedron Suppl. 8, 359 (1966). Stereochemistry: D. Arigoni, Pure Appl. Chem. 17, 331 (1968). Fermentation and biosynthetic study: F. Knauseder, E. Brandl, J. Antibiot. 29, 125 (1976). Mechanism of action: G. Hoegenauer, Antibiotics vol. 5, pt. 1, F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) p 344. Synthetic studies: E. G. Gibbons, J. Org. Chem. 45, 1540 (1980); M. Kahn, Tetrahedron Lett. 21, 4547 (1980). Total synthesis: E. G. Gibbons, J. Am. Chem. Soc. 104, 1767 (1982).
Properties: Crystals from ethyl acetate + Skellysolve B, mp 170-171°. [a]D24 +20° (c = 3 in abs ethanol). uv max (5 mg/ml in 95% ethanol): 290 nm. Soluble in methanol, ethanol, ethyl acetate, chloroform. LD50 in mice: >60 mg/kg (Kavanagh, 1952).
Melting point: mp 170-171°
Optical Rotation: [a]D24 +20° (c = 3 in abs ethanol)
Absorption maximum: uv max (5 mg/ml in 95% ethanol): 290 nm
Toxicity data: LD50 in mice: >60 mg/kg (Kavanagh, 1952)
 
Derivative Type: Diacetate
Molecular Formula: C26H38O7
Molecular Weight: 462.58
Percent Composition: C 67.51%, H 8.28%, O 24.21%
Properties: Crystals from abs ethanol, mp 145.5°.
Melting point: mp 145.5°

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