143. Actiphenol
Nomenclature
CAS number: 526-02-3
4-[2-(2-Hydroxy-3,5-dimethylphenyl)-2-oxoethyl]-2,6-piperidinedione; 3-(2-hydroxy-3,5-dimethylphenacyl)glutarimide; β-(3,5-dimethyl-2-hydroxybenzoylmethyl)glutarimide; C-73. C15H17NO4; mol wt 275.30.
C 65.44%, H 6.22%, N 5.09%, O 23.25%.
Description and references
Metabolic product found in culture filtrates of cycloheximide-producing actinomycetes (Streptomyces albulus): Highet, Prelog, Helv. Chim. Acta 42, 1523 (1959); Rao, J. Org. Chem. 25, 661 (1960). Synthesis: Johnson, ibid. 27, 3658 (1962). May be prepd from cycloheximide: Highet, Prelog, loc. cit. Structure-activity studies: Ennis, Biochem. Pharmacol. 17, 1197 (1968).
Properties
Fluffy needles from methylene chloride + methanol. mp 200-202°. Pure crystals are white or colorless. uv max: 262, 345 nm (ε 10870, 4550). Exhibits bright yellow fluorescence under u.v. Soluble in aqueous NaOH (forming bright yellow solns), in anhydr alcohol, tetrahydrofuran. Insol in aq solns of sodium bicarbonate.Derivative
Acetate.C17H19NO5; mol wt 317.34.
C 64.34%, H 6.03%, N 4.41%, O 25.21%.