1-OCTEN-3-OL

Chemical properties

1-OCTEN-3-OL is a colorless liquid. B.P. 175° C. Sp.Gr. 0.84. Very powerful, sweet-earthy, almost buttery and fungus- or fermentation-like odor with a strong herbaceous note, -suggestive of Lavender-Lavandin-Rose and Hay. Somewhat acridchemical undertone which is hardly perceptible at proper (high) dilution. Almost insoluble in water, soluble in alcohol and oils. Sweet-herbaceous, haylike-earthy taste.

Occurrence

Originally reported to be found in the mushroom Armillaria matsutake, a parasite growing on the radical hairs of Pinus densiflora in the forests of Japan. It has been isolated also from the essential oils of Mentha pulegium L., lavender and M. timjia.

The Uses of 1-OCTEN-3-OL

1-OCTEN-3-OL has been identified in Lavandin and many other important essential oils, it has become extremely popular in the art and science of preparing artificial or "reconstituted" essential oils. This is where the alcohol finds its main outlet. It also used in flavors (and in artificial Spearmint), such as Spice, Fruit, etc. usuall> in very low concentration: 0.2 to 6 ppm in the finished consumer product.

Preparation

By a vinyl Grignard reaction on hexaldehyde or from amyl magnesium bromide and acrolein.

Metabolism

In the animal body secondary alcohols can undergo either conjugation with glucuronic acid or oxidation to a ketone, which may be excreted in the urine or expired air or further oxidized or reduced back to the alcohol. Studies of secondary alcohols containing more than seven carbon atoms have been limited to octan-2-ol. The conjugation of this alcohol in rabbits is low and much of the alcohol may be excreted unchanged . A dilute solution of synthetic (dl)-locten-3-ol fed directly into the rumen of a cow produced after 2-4 hr a maximum concentration in the milk of 20 μg octenol/litre. This concentration did not give the milk an off-flavour, and was not reported to have any other effects.