9806. Tuberin
Nomenclature
CAS number: 53643-53-1
N-[2-(4-Methoxyphenyl)ethenyl]formamide; N-trans-(p-methoxystyryl)formamide; N-formyl trans-p-methoxystyrylamine. C10H11NO2; mol wt 177.20.
C 67.78%, H 6.26%, N 7.90%, O 18.06%.
Description and references
Antitubercular antibiotic isolated from the broth filtrate of Streptomyces amakusaensis: Ohkuma et al., J. Antibiot. 15A, 115 (1962); Sumiki et al., JP 64 7399 (1964 to Inst. Phys. & Chem. Res.), C.A. 62, 8355g (1965). Structure and synthesis: Anzai et al., J. Antibiot. 15A, 110, 117, 123 (1962). Alternate synthesis: I. J. Massey, I. T. Harrison, Chem. Ind. (London) 1977, 920. Biosynthetic studies: K. M. Cable et al., J. Chem. Soc. Perkin Trans. 1 1987, 1593.
Properties
Prisms from benzene, mp 132-133°. Stable in weakly acidic or weakly alkaline solns. uv max (methanol): 219, 285 nm (E1%1cm 870, 1710). Sol in the lower alcohols, ethyl acetate, acetone; moderately sol in carbon tetrachloride, chloroform; sparingly sol in water, benzene. Practically insol in petr ether.Derivative
Dihydrotuberin.C10H13NO2; mol wt 179.22.
C 67.02%, H 7.31%, N 7.82%, O 17.85%.