On Some Ferulates

Abstract

Eicosanyl-ferulate mp 5354°C (I) and dihydro-β-sitosteryl-ferulate mp 156157°C (II) were prepared by the condensation of ferulic acid with eicosanol and dihydro-β-sitosterol, respectively. The ferulate (I) was identical to the naturally occurring ferulate isolated in our laboratory from linseed oil and rapeseed oil; and the latter (II) was also identical to that from corn (maize)-germ oil.Ethyl-, mp 4142°C and 57°C, lauryl-, mp 45°C, cholesteryl-, mp 165166°C, β-sitosteryl-, mp 123°C, stigmasterylferulate mp 147148°C and some acyl-derivatives were also prepared, and these characteristics were observed (Table-1).Chlorination_ by oxalyl chloride was mainly applied to this reaction. As a results, acylated ferulic acid chloride was obtained at high yield.The difference between molecular rotations of the above ferulates and those of the original sterols in Δ5-series, were +147+198 in the ranges, and seemed to be obviously greater than the molecular rotation differences in other series (Table-2).The difference in weight increases between those mice ((_??_), 25-days-old) breeded for 28 days by the various feeds in which ferulic acid and its derivatives were added, and the mice breeded by the non-additional standard feed for same days were not recognized (Fig. 1).But, mice ((_??_), 100-days-old), breeded by the feeds in which cholesteryl-ferulate and ferulic acid plus sodium bicarbonate respectively, increased their weight compared with those breeded by the non-additional standard feed, and the results were as follows : non-additional standard feed100g of standard feed+ 12 mg of cholesteryl-ferulate100 g of standard feed+0.08 mg of ferulic acid and 0.04 mg of sodium bicarbonate after 2 weeks 100.5% 105.1% 107.4%after 4 weeks 105.7% 110.8% feed gathered mold