alpha-Spinasterol

Title: a-Spinasterol
CAS Registry Number: 481-18-5
CAS Name: (3b,5a,22E)-Stigmasta-7,22-dien-3-ol
Additional Names: a-spinasterin; bessisterol; hitodesterol
Molecular Formula: C29H48O
Molecular Weight: 412.69
Percent Composition: C 84.40%, H 11.72%, O 3.88%
Literature 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.
Properties: Crystals from alcohol + light petr, mp 168-169°. [a]D25 -3.6° (c = 2.8 in chloroform).
Melting point: mp 168-169°
Optical Rotation: [a]D25 -3.6° (c = 2.8 in chloroform)
Derivative Type: Benzoate
Molecular Formula: C36H52O2
Molecular Weight: 516.80
Percent Composition: C 83.67%, H 10.14%, O 6.19%
Properties: Plates from ethyl acetate, mp 200°. [a]D25 +1.8° (c = 1.7 in chloroform).
Melting point: mp 200°
Optical Rotation: [a]D25 +1.8° (c = 1.7 in chloroform)
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