Title: Actiphenol

CAS Registry Number: 526-02-3

CAS Name: 4-[2-(2-Hydroxy-3,5-dimethylphenyl)-2-oxoethyl]-2,6-piperidinedione

Additional Names: 3-(2-hydroxy-3,5-dimethylphenacyl)glutarimide; b-(3,5-dimethyl-2-hydroxybenzoylmethyl)glutarimide

Manufacturers' Codes: C-73

Molecular Formula: C15H17NO4

Molecular Weight: 275.30

Percent Composition: C 65.44%, H 6.22%, N 5.09%, O 23.25%

Literature 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 (e 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.

Melting point: mp 200-202°

Absorption maximum: uv max: 262, 345 nm (e 10870, 4550)

 

Derivative Type: Acetate

Molecular Formula: C17H19NO5

Molecular Weight: 317.34

Percent Composition: C 64.34%, H 6.03%, N 4.41%, O 25.21%

Properties: Crystals from methylene chloride + ether, mp 155.5°.

Melting point: mp 155.5°