Title: Candidin
CAS Registry Number: 1405-90-9
Molecular Formula: C47H71NO17
Molecular Weight: 922.06
Percent Composition: C 61.22%, H 7.76%, N 1.52%, O 29.50%
Literature References: Main component of an antifungal antibiotic complex produced by the soil actinomycete Streptomyces viridoflavus: W. A. Taber et al., Antibiot. Chemother. 4, 455 (1954); L. C. Vining et al., Antibiot. Annu. 2, 980 (1954-1955); L. C. Vining, W. A. Taber, Can. J. Chem. 34, 1163 (1956). The two other active principles are designated as candidinin and candidoin. Prepn of pure crystalline candidin: Preud'hamme, Vuillemin, FR 1298345 (1962 to Rhone-Poulenc), C.A. 58, 420c (1963). Synthesis: M. Subramanian et al., J. Nat. Prod. 55, 1213 (1992). Structure: Borowski et al., Tetrahedron Lett. 1971, 1987; and NMR characterization: J. Pawlak et al., J. Antibiot. 46, 1598 (1993). Antifungal activity studies: Solotorovsky et al., Antibiot. Chemother. 8, 364 (1958).
Properties: Golden-yellow needles from methanol + chloroform + water. Does not melt, but darkens slowly above 180°. [a]D27 +363° (c = 0.3 in DMF); [a]D27 +205° (c = 0.3 in glacial acetic acid). uv max (methanol): 406, 383, 362, 347 nm. Practically insol in water and most organic solvents. Moderately sol in glacial acetic acid, pyridine, DMF. LD50 in mice (mg/kg): 1.5 i.v., >100 orally, 30 s.c. (Vining et al.).
Optical Rotation: [a]D27 +363° (c = 0.3 in DMF); [a]D27 +205° (c = 0.3 in glacial acetic acid)
Absorption maximum: uv max (methanol): 406, 383, 362, 347 nm
Toxicity data: LD50 in mice (mg/kg): 1.5 i.v., >100 orally, 30 s.c. (Vining et al.) |