9023. Tachysterol
Nomenclature
CAS number: 115-61-7
(3β,6E,22E)-9,10-Secoergosta-5(10),6,8,22-tetraen-3-ol. C28H44O; mol wt 396.65.
C 84.78%, H 11.18%, O 4.03%.
Description and references
From ergosterol or lumisterol by ultraviolet irradiation: Windaus et al., Ann. 492, 226 (1932); Ann. 499, 188 (1932); Dimroth, Ber. 70, 1631 (1937). From calciferol by adsorption on acid clay: Thibaudet, Compt. Rend. 220, 751 (1945). From precalciferol: Velluz, Goffinet, US 2847426 (l958 to UCLAF). Structure: Grundmann, Z. Physiol. Chem. 252, 151 (1938); Thibaudet, loc. cit. Stereochemistry of the tachysterol system: Inhoffen, Ber. 88, 1424 (1955); Verloop, Rec. Trav. Chim. 76, 689 (1957); Delaroff et al., Bull. Soc. Chim. Fr. 1963, l739.
Properties
Oil. [α]D18 70° (24.6 mg in 2 ml petr ether); [α]18546 86.3° (petr ether). uv max: 280 nm. Not pptd by digitonin. Insol in water. Sol in organic solvents, but not in methanol. Very easily oxidized by air.Derivative
4-Methyl-3,5-dinitrobenzoate.C36H48N2O6; mol wt 604.78.
C 71.49%, H 8.00%, N 4.63%, O 15.87%.