Title: Lupeol
CAS Registry Number: 545-47-1
CAS Name: (3b)-Lup-20(29)-en-3-ol
Additional Names: monogynol B; b-viscol; fagarasterol
Molecular Formula: C30H50O
Molecular Weight: 426.72
Percent Composition: C 84.44%, H 11.81%, O 3.75%
Literature 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 b-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).
Properties: Needles from alcohol or acetone, mp 215°. [a]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.
Melting point: mp 215°
Optical Rotation: [a]D20 +27.2° (c = 4.8 in chloroform)
Derivative Type: Acetate
Molecular Formula: C32H52O2
Molecular Weight: 468.75
Percent Composition: C 81.99%, H 11.18%, O 6.83%
Properties: Needles from acetone, mp 218°. [a]D20 +47.3° (c = 2 in chloroform).
Melting point: mp 218°
Optical Rotation: [a]D20 +47.3° (c = 2 in chloroform)
Derivative Type: Benzoate
Molecular Formula: C37H54O2
Molecular Weight: 530.82
Percent Composition: C 83.72%, H 10.25%, O 6.03%
Properties: Prisms from acetone, mp 273-274°. [a]D20 +61° (0.78 g in 25 ml chloroform).
Melting point: mp 273-274°
Optical Rotation: [a]D20 +61° (0.78 g in 25 ml chloroform)
Derivative Type: Hydrochloride
Molecular Formula: C30H50O.HCl
Molecular Weight: 463.18
Percent Composition: C 77.79%, H 11.10%, O 3.45%, Cl 7.65%
Properties: Needles from ethanol, mp 211-212°. [a] -31° (c = 1.1 in chloroform).
Melting point: mp 211-212°
Optical Rotation: [a] -31° (c = 1.1 in chloroform)
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