8749. α-Spinasterol

Nomenclature

CAS number: 481-18-5
(3β,5α,22E)-Stigmasta-7,22-dien-3-ol; α-spinasterin; bessisterol; hitodesterol.
C29H48O; mol wt 412.69.
C 84.40%, H 11.72%, O 3.88%.

Description and references

Stereoisomeric with chondrillasterol, q.v. Extracted from spinach leaves: Hart, Heyl, J. Biol. Chem. 95, 311 (1932); from Citrullus colocynthis Schrad., Cucurbitaceae: Hamilton, Kermack, J. Chem. Soc. 1952, 5051. Structure: Fieser et al., J. Am. Chem. Soc. 71, 2226 (1949). Prepn: Kircher, Rosenstein, J. Org. Chem. 38, 2259 (1973); M. Anastasia et al., J. Chem. Soc. Perkin Trans. 1 1981, 2561.

Chemical structure

Properties

Crystals from alcohol + light petr, mp 168-169°. [α]D25 3.6° (c = 2.8 in chloroform).

Derivative

Benzoate.
C36H52O2; mol wt 516.80.
C 83.67%, H 10.14%, O 6.19%.

Properties

Plates from ethyl acetate, mp 200°. [α]D25 +1.8° (c = 1.7 in chloroform).