Title: Picromycin
CAS Registry Number: 19721-56-3
Additional Names: (E)-14-Ethyl-13-hydroxy-3,5,7,9,13-pentamethyl-6-[[3,4,6-trideoxy-3-(dimethylamino)-b-D-xylo-hexopyranoside]oxy]oxacyclotetradec-11-ene-2,4,10-trione; pikromycin; albomycetin; amaromycin
Molecular Formula: C28H47NO8
Molecular Weight: 525.67
Percent Composition: C 63.98%, H 9.01%, N 2.66%, O 24.35%
Literature References: First macrolide antibiotic isolated. Isoln from Actinomyces spp by Lindenbein and Bauer, see Brockmann, Henkel, Naturwissenschaften 37, 138 (1950); Ber. 84, 284 (1951); Brockmann, Bohne, US 2693433 (1954 to Schenley). Structure: Brockmann, Oster, Ber. 90, 605 (1957); Anliker, Gubler, Helv. Chim. Acta 40, 119, 1768 (1957). Studies in stereochemistry: Djerassi, Halpern, J. Am. Chem. Soc. 79, 3926 (1957); Ogura et al., ibid. 97, 1930 (1975); eidem, Tetrahedron 37, Suppl. 1, 165 (1981). Revised structure: Rickards, Smith, Chem. Commun. 1968, 1049; Muxfeldt et al., J. Am. Chem. Soc. 90, 4748 (1968). Synthesis from narbonolide: Maezawa et al., J. Antibiot. 26, 771 (1973).
Properties: Very bitter, rectangular platelets from methanol, mp 169.5-170°. Stable to heat. [a]D24 +8.2° (c = 3.5 in ethanol); [a]D20 -33.5° (c = 2.07 in chloroform); [a]D24 -50.2° (c = 6.3 in chloroform). uv max (ethanol): 225 nm (log e 3.97). Rotary dispersion data: Djerassi, Halpern, Tetrahedron 3, 268 (1958). Very sparingly sol in water, petr ether, carbon disulfide. Soly in ethanol: 3.5 g/100 ml at 20°. Freely sol in acetone, benzene, chloroform, ethyl acetate, dioxane. Moderately sol in ether, methanol.
Melting point: mp 169.5-170°
Optical Rotation: [a]D24 +8.2° (c = 3.5 in ethanol); [a]D20 -33.5° (c = 2.07 in chloroform); [a]D24 -50.2° (c = 6.3 in chloroform)
Absorption maximum: uv max (ethanol): 225 nm (log e 3.97) |