Title: Pterocarpin
CAS Registry Number: 524-97-0
CAS Name: (6aR-cis)-6a,12a-Dihydro-3-methoxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran
Molecular Formula: C17H14O5
Molecular Weight: 298.29
Percent Composition: C 68.45%, H 4.73%, O 26.82%
Literature References: From red sandalwood (Pterocarpus santalinus L.f., Leguminosae): Cazeneuve, Hugouneng, Compt. Rend. 104, 1722 (1887); 107, 737 (1888); Leonhardt, Fay, Arch. Pharm. 273, 53 (1935); McGookin et al., J. Chem. Soc. 1940, 787; from Pterocarpus spp: King et al., ibid. 1953, 3693. Structure: Bredenberg, Shoolery, Tetrahedron Lett. 1961, 285. Synthesis of the dl-form: Fukui, Nakayama, ibid. 1966, 1805; eidem, Bull. Chem. Soc. Jpn. 42, 1408 (1969); Uchiyama, Matsui, Agric. Biol. Chem. 31, 1490 (1967). Stereochemistry: Ito et al., Chem. Commun. 1965, 595; Pachler, Underwood, Tetrahedron 23, 1817 (1967).
Properties: Crystalline plates from petr ether or from ethanol, mp 164.5°. [a]D -214.5° and [a]20.55461 -207.5° (c = 0.53 in chloroform). Practically insol in water, cold alcohol or ether. Sol in hot alcohol, chloroform.
Melting point: mp 164.5°
Optical Rotation: [a]D -214.5°; [a]20.55461 -207.5° (c = 0.53 in chloroform) |