Title: Parthenin
CAS Registry Number: 508-59-8
CAS Name: [3aS-(3aa,6b,6aa,9ab,9ba)]-3,3a,4,5,6,6a,9a,9b-Octahydro-6a-hydroxy-6,9a-dimethyl-3-methyleneazuleno[4,5-b]furan-2,9-dione
Additional Names: 1,6b-dihydroxy-4-oxo-10aH-ambrosa-2,11(13)-dien-12-oic acid g-lactone; parthenicin
Molecular Formula: C15H18O4
Molecular Weight: 262.30
Percent Composition: C 68.68%, H 6.92%, O 24.40%
Literature References: From herb of Parthenium hysterophorus L., Compositae. Parthenin is the substance largely responsible for the allergic contact dermatitis caused by P. hysterophorus. Isoln: Arny, Am. J. Pharm. 69, 169 (1897). Isoln and structure: Herz et al., Tetrahedron Lett. 1961, 82; Herz et al., J. Am. Chem. Soc. 84, 2601 (1962). Abs config: Emerson et al., Tetrahedron Lett. 1966, 6151. Total synthesis of (±)-form: P. Kok et al., Bull. Soc. Chim. Belg. 87, 615 (1978); C. H. Heathcock et al., J. Am. Chem. Soc. 104, 6081 (1982).
Properties: Crystals from water, mp 163-166°. [a]D25 +7.02° (c = 2.71 in chloroform). uv max: 215, 340 nm (e 15,100; 22). Practically insol in water. Sol in alcohol, chloroform, ether, ethyl acetate.
Melting point: mp 163-166°
Optical Rotation: [a]D25 +7.02° (c = 2.71 in chloroform)
Absorption maximum: uv max: 215, 340 nm (e 15,100; 22) |