References of (3S,5S,9R,10S,13R,14R,17R)-17-[(E,2R,
5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,
15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Title: a-Spinasterol
CAS Registry Number: 481-18-5
CAS Name: (3b,5a,22
E)-Stigmasta-7,22-dien-3-ol
Synonyms: 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)