617. α-Amyrin

Nomenclature

CAS number: 638-95-9
(3β)-Urs-12-en-3-ol; α-amyrenol; viminalol.
C30H50O; mol wt 426.72.
C 84.44%, H 11.81%, O 3.75%.

Description and references

Occurs mostly as acetate in latex of rubber trees, in latex from Ficus variegata Blume, Moraceae, also in Balanophora elongata Blume, Balanophoraceae, and in Erythroxylum coca Lam. var. novogranatense Morris, and var. spruceanum Burck, Erythroxylaceae. Isoln from Manila elemi: Vesterberg, Westerlind, Ann. 428, 247 (1922). Structural studies: Spring, Vickerstaff, J. Chem. Soc. 1937, 249; Beynon et al., ibid. 1938, 1233; Meisels et al., Helv. Chim. Acta 32, 1075 (1949), 38, 1298 (1955); Melera et al., ibid. 39, 441 (1956). Identity with viminalol: Soldin, Marais, J. Pharm. Soc. 55, 452 (1966). Formation from ursolic acid: Goodson, J. Chem. Soc. 1938, 999; from boswellic acid: Ruzicka, Wirz, Helv. Chim. Acta 22, 948 (1939). Partial synthesis from glycyrrhetic acid and stereochemistry: Corey, Cantrall, J. Am. Chem. Soc. 81, 1745 (1959). Review: J. Simonsen, W. C. J. Ross, The Terpenes vol. IV (University Press, Cambridge, 1957) pp 116-148.

Chemical structure

Properties

Needles from alcohol, mp 186°. bp0.7 243°. [α]D17 +91.6° (c = 1.3 in benzene). Sol in 22 parts 98% alc. Sol in ether, benzene, chloroform, glacial acetic acid. Slightly sol in petr ether.

Derivative

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

Properties

Leaflets from petr ether, mp 227°. [α]D20 +76.35° (c = 0.572 in CHCl3).

Derivative

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

Properties

Prisms from benzene + acetone, mp 195-196°. [α]D10 +94.6° (c = 1.9 in CHCl3).