2872. Dehydroergosterol

Nomenclature

CAS number: 516-85-8
(3β,22E)-Ergosta-5,7,9(11),22-tetraen-3-ol.
C28H42O; mol wt 394.63.
C 85.22%, H 10.73%, O 4.05%.

Description and references

Prepd from ergosterol: Windhaus, Linsert, Ann. 465, 148 (1928); Callow, Rosenheim, J. Chem. Soc. 1933, 387. From isopyrocalciferol: Windhaus, Dimroth, Ber. 70, 376 (1937).

Chemical structure

Properties

Solvated plates from alcohol, needles from ether. When dry, mp 146°. bp0.5 230°. [α]D15 +149.2° (c = 1.9 in chloroform). Absorption spectrum: Morton, de Gouveia, J. Chem. Soc. 1934, 916. One gram dissolves in 800 ml methanol. Freely sol in ether, chloroform, benzene.

Derivative

Acetate.
C30H44O2; mol wt 436.67.
C 82.52%, H 10.16%, O 7.33%.

Properties

mp 146°. [α]D16 +204° (c = 1.1 in chloroform).

Derivative

Methyl ether.
C29H44O; mol wt 408.66.
C 85.23%, H 10.85%, O 3.92%.

Properties

mp 106°. [α]D20 +166° (c = 2 in chloroform).