12-09173. Sumatrol [Archived]

Nomenclature

CAS number: 82-10-0
[2R-(2α,6aα,12aα)]-1,2,12,12a-Tetrahydro-5-hydroxy-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one.
C23H22O7; mol wt 410.42.
C 67.31%, H 5.40%, O 27.29%.

Description and references

Present in resin from Derris sp., Leguminosae: Robertson, Rusby, J. Chem. Soc. 1937, 497. Isolated also from Tephrosia toxicaria Pers., Papilionaceae: Harper, ibid. 1940, 1178. Structure and stereochemistry: Harper, loc. cit.; Crombie, Peace, ibid. 1961, 5445.

Chemical structure

Properties

Needles from alcohol, mp 195-196°. Needles from acetone, mp 183°; melts again at 194° after keeping for several days. [α]D20 182° (c = 2.84 in benzene). Absorption max: 670 nm (ε 4660). Practically insol in water; sparingly sol in methanol, cold acetic acid, moderately sol in benzene, ethyl acetate; sol in chloroform.

Status

This monograph has been retired and is no longer subject to revision or update.