Title: Frenolicin
CAS Registry Number: 10023-07-1
CAS Name: [1R-(1a,3b,4ab,10ab)]-3,4,5,10-Tetrahydro-9-hydroxy-5,10-dioxo-1-propyl-4a,10a-epoxy-1H-naphtho[2,3-c]pyran-3-acetic acid
Molecular Formula: C18H18O7
Molecular Weight: 346.33
Percent Composition: C 62.42%, H 5.24%, O 32.34%
Literature References: Antibiotic produced by Streptomyces fradiae: Van Meter et al., Antimicrob. Agents Annu. 1960, 77. Structure: Ellestad et al., J. Am. Chem. Soc. 88, 4109 (1966); 90, 1325 (1968). Total synthesis: A. Ichihara et al., Tetrahedron Lett. 21, 4469 (1980).
Properties: Pale yellow needles from benzene, mp 160-161°. [a]D25 -37.7° (c = 1.5 in methanol). uv max (methanol): 234, 362 nm (e 18300, 5200). Sol in methanol, ethanol, ethyl acetate, acetone, glacial acetic acid, carbon tetrachloride; slightly sol in benzene. Practically insol in water, cyclohexane, petr ether.
Melting point: mp 160-161°
Optical Rotation: [a]D25 -37.7° (c = 1.5 in methanol)
Absorption maximum: uv max (methanol): 234, 362 nm (e 18300, 5200) |