Primocarcin
Title: Primocarcin
CAS Registry Number: 3750-26-3
CAS Name: 5-(Acetylamino)-4-oxo-5-hexenamide
Additional Names: 4-acetamido-4-penten-3-one-1-carboxamide
Molecular Formula: C8H12N2O3
Molecular Weight: 184.19
Percent Composition: C 52.17%, H 6.57%, N 15.21%, O 26.06%
Literature References: Antineoplastic antibiotic produced by the actinomycete, Nocardia fukaya. Isoln: Y. Sumiki et al., J. Antibiot. 13A, 416 (1960); Isono, Suzuki, ibid. 15A, 77 (1962). Isoln from Streptomyces diastatochromogens var. luteus: H. Abe et al., ibid. 20A, 167 (1967). Structure: Isono, ibid. 15A, 80 (1962). Synthesis: Bowman et al., J. Chem. Soc. 1965, 470.
Properties: Needles from hot methanol, mp 130-131°. Sol in water, lower alcohols, acetone, pyridine; slightly sol in most other organic solvents. Aq soln stable from pH 5-8. uv max (water): 253 nm (e 3420); in 0.1N NaOH: 215, 347 nm (e 3230, 304). LD50 in mice (mg/kg): 50-60 i.p.; 300 i.v. (Isono, Suzuki).
Melting point: mp 130-131°
Absorption maximum: uv max (water): 253 nm (e 3420); in 0.1N NaOH: 215, 347 nm (e 3230, 304)
Toxicity data: LD50 in mice (mg/kg): 50-60 i.p.; 300 i.v. (Isono, Suzuki)
 
Derivative Type: Dihydroprimocarcin
Molecular Formula: C8H14N2O3
Molecular Weight: 186.21
Percent Composition: C 51.60%, H 7.58%, N 15.04%, O 25.78%
Properties: Plates from acetone, mp 137-141°.
Melting point: mp 137-141°
 
Derivative Type: Tetrahydroprimocarcin
Molecular Formula: C8H16N2O3
Molecular Weight: 188.22
Percent Composition: C 51.05%, H 8.57%, N 14.88%, O 25.50%
Properties: Needles from methanol + acetone, mp 183°.
Melting point: mp 183°

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