Title: Pterocarpin
CAS Registry Number: 524-97-0
CAS Name: (6a
R-cis)-6a,12a-Dihydro-3-methoxy-6
H-[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)