7932. Pterocarpin

Nomenclature

CAS number: 524-97-0
(6aR-cis)-6a,12a-Dihydro-3-methoxy-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran.
C17H14O5; mol wt 298.29.
C 68.45%, H 4.73%, O 26.82%.

Description and 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).

Chemical structure

Properties

Crystalline plates from petr ether or from ethanol, mp 164.5°. [α]D -214.5° and [α]20.55461 -207.5° (c = 0.53 in chloroform). Practically insol in water, cold alcohol or ether. Sol in hot alcohol, chloroform.