3835. Ethyl Oenanthate

Nomenclature

CAS number: 106-30-9
Heptanoic acid ethyl ester; ethyl heptanoate; ethyl n-heptoate; oenanthic ether; cognac oil, synthetic; oil of grapes; aether oenanthicus; oleum vitis viniferae.
C9H18O2; mol wt 158.24.
C 68.31%, H 11.47%, O 20.22%.

Description and references

Obtained commercially either by esterification of heptanoic acid, yielding a high-grade product; or by the direct esterification of coconut oil yielding a mixture of the ethyl esters of lauric, myristic, palmitic, and other higher fatty acids plus ethyl and isoamyl alcohol. For some flavoring applications the latter product is more desirable. Prepn: Rogers, J. Am. Pharm. Assoc. Sci. Ed. 12, 503 (1923). Toxicity: P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964).

Chemical structure

Properties

Pure ester, liquid. Fruity, wine-like odor and taste with burning aftertaste. d415 0.8723; d425 0.8630. bp760 189°; bp35 95°; bp8 68°. Viscosity at 25°: 0.0111 g/cm/sec. Insol in water. Misc with alcohol, ether, chloroform. Forms an azeotrope with water, the azeotropic mixture boils at 98.5° and contains 72% w/w of ethyl oenanthate. LD50 orally in rats: >34640 mg/kg (Jenner).

Note

Artificial Ethyl Oenanthate, also known as artificial cognac essence or oil of wine, is a mixture of amyl and ethyl caprates with ethyl and isoamyl butyrates and caprylates.

Use

In the manuf of liqueurs. Plays an important part in the formulation of raspberry, gooseberry, grape, cherry, apricot, currant, bourbon, and other artificial essences.