Ceryl Alcohol from the Grass,Agrostis

Abstract

Bondzynski and Humnicki 1 isolated from horse dung an unsaponifiable substance which they named hippocoprosterol. It was assumed to be a reduced sterol, analogous to coprosterol, but representing a greater degree of reduction. It was later obtained, impure, by Wilenko. 2 Dorée and Gardner 3 observed that hippocoprosterol from the horse, cow, sheep, and rabbit is not a product of sterol metabolism, but is merely an unaltered constituent of the grass ingested by these herbivora. Considering its origin, they renamed it chortosterol.

Collison and MacLean 4 observed recently that the alcoholic constituent of spinach leaves is identical with the ceryl alcohol of Chinese insect wax. Similarity in physical properties and percentage composition suggested to us that all these products are essentially one and the same substance. Experiments were begun with the grass known as bent, but they were discontinued after we saw the comprehensive report by Pollard, Chibnall and Piper. 5 These workers indicated that hippocoprosterol is ceryl alcohol, the latter being defined as a fatty alcohol mixture having a mean carbon content of about C₂₇ and a melting point of about 80°. In cocksfoot and perennial ryegrass they found the ceryl alcohol to consist predominantly of n-hexacosanol.

Our limited experiments with a third species of grass confirm this work. The bent, Agrostis (Sp.), was obtained as clippings from a putting green almost free of other vegetation. Air-dried, it was extracted with hexane, and the crude wax was boiled with alcoholic KOH. The solution was treated with alcoholic CaCl₂, filtered hot, and cooled to 20°. The crude ceryl alcohol was treated with charcoal in hexane, and again in benzene. The yield, after losses, was about 1% of the dry grass.