5608. Lupeol

Nomenclature

CAS number: 545-47-1
(3β)-Lup-20(29)-en-3-ol; monogynol B; β-viscol; fagarasterol.
C30H50O; mol wt 426.72.
C 84.44%, H 11.81%, O 3.75%.

Description and references

Abundant plant triterpene. Occurs in the skin of lupin seeds, in chicle, in the latex of fig trees and of rubber plants. Was detected in cocoons of Bombyx mori. Isoln: Cohen, Rec. Trav. Chim. 28, 368 (1909); Ruzicka et al., Helv. Chim. Acta 20, 1567 (1937). Identity with β-viscol: Meyer, Jeger, ibid. 31, 1868 (1948). Identity with monogynol B: Chatterji et al., J. Sci. Ind. Res. 18B, 262 (1959). Structure: Ruzicka et al., Helv. Chim. Acta 28, 942 (1945); Ames et al., J. Chem. Soc. 1951, 450. Structure of hydrochloride: Halsall et al., ibid. 1952, 2862. Configuration: Barton, Holmes, ibid. 1952, 78; Djerassi et al., J. Am. Chem. Soc. 77, 5330 (1955). NMR studies: Buckley et al., Chem. Ind. (London) 1971, 298. Total synthesis: Stork et al., J. Am. Chem. Soc. 93, 4945 (1971).

Chemical structure

Properties

Needles from alcohol or acetone, mp 215°. [α]D20 +27.2° (c = 4.8 in chloroform). Freely sol in ether, benzene, petr ether, warm alcohol. Practically insol in water, dil acid and alkalies.

Derivative

Acetate.
C32H52O2; mol wt 468.75.
C 81.99%, H 11.18%, O 6.83%.

Properties

Needles from acetone, mp 218°. [α]D20 +47.3° (c = 2 in chloroform).

Derivative

Benzoate.
C37H54O2; mol wt 530.82.
C 83.72%, H 10.25%, O 6.03%.

Properties

Prisms from acetone, mp 273-274°. [α]D20 +61° (0.78 g in 25 ml chloroform).

Derivative

Hydrochloride.
C30H50O.HCl; mol wt 463.18.
C 77.79%, H 11.10%, O 3.45%, Cl 7.65%.

Properties

Needles from ethanol, mp 211-212°. [α] 31° (c = 1.1 in chloroform).