Title: Ustilagic Acid

CAS Registry Number: 8002-36-6

Additional Names: Ustizeain B

Literature References: C37H62-66O17; mol wt about 780. A mixture of partially acylated derivatives of a di-D-glucosyldihydroxyhexadecanoic acid. Antibiotic substance produced by the corn smut fungus Ustilago zeae: Haskins, Can. J. Res. 28C, 213 (1950); Lemieux et al., Can. J. Chem. 29, 409, 415 (1951); Reed, Holder, Can. J. Med. Sci. 31, 505 (1953); Haskins, US 2698843 (1955 to National Research Council, Canada). Biosynthesis: Boothroyd et al., Can. J. Biochem. Physiol. 33, 289 (1955). Production by submerged culture: Lemieux, CA 600121 (1960 to National Research Council, Canada).

Properties: Long crystals from ether, mp 146-147°. [a]D23 +7° (pyridine). Freely sol in methanol, pyridine, 2,3-butanediol, 1,2-propanediol. Sparingly sol in ethanol, butanol, acetone. Insol in water, glycerol, ethyl acetate, ether, benzene, petr ether. Shows in vitro activity against Cryptococcus neoformans, Candida albicans, and some saprophytic fungi. Practically ineffective in rabbits and mice suffering from fungus diseases.

Melting point: mp 146-147°

Optical Rotation: [a]D23 +7° (pyridine)