Enanthic acid, also called heptanoic acid, is an organic compound composed of a seven-carbon chain terminating in a

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

functional group. It is a colorless oily liquid with an unpleasant, rancid odor. It contributes to the odor of some rancid oils. It is slightly soluble in water, but very soluble in ethanol and ether. Salts and esters of enanthic acid are called enanthates or heptanoates. Its name derives from the Latin '' oenanthe'' which is in turn derived from the Ancient Greek ''oinos'' "wine" and ''anthos'' "blossom."

Production

The methyl ester of ricinoleic acid, obtained from castor bean oil, is the main commercial precursor to enanthic acid. It is pyrolyzed to the methyl ester of

10-undecenoic acid Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the sk ...

and

heptanal Heptanal or heptanaldehyde is an alkyl aldehyde. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants. Production The formation of heptanal in the fractional distillation of cas ...

, which is then air-oxidized to the carboxylic acid. Approximately 20,000 tons were consumed in Europe and US in 1980.David J. Anneken, Sabine Both, Ralf Christoph, Georg Fieg, Udo Steinberner, Alfred Westfechtel "Fatty Acids" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. Laboratory preparations of enanthic acid include permanganate oxidation of

and

1-octene 1-Octene is an organic compound with a formula CH2CHC6H13. The alkene is classified as a higher olefin and alpha-olefin, meaning that the double bond is located at the alpha (primary) position, endowing this compound with higher reactivity and thu ...

Uses

Enanthic acid is used in the preparation of esters, such as

ethyl enanthate Ethyl heptanoate is the ester resulting from the condensation of heptanoic acid and ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chem ...

, which are used in fragrances and as artificial flavors. Enanthic acid is used to esterify steroids in the preparation of drugs such as

testosterone enanthate Testosterone enanthate, sold under the brand names Delatestryl and Xyosted among others, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of low testosterone levels in men. It is also used in hormone th ...

trenbolone enanthate Trenbolone enanthate, known by the nickname Trenabol, is a synthetic and injected anabolic–androgenic steroid (AAS) and a derivative of nandrolone which was never marketed. It is the C17β enanthate ester and a long-acting prodrug of trenbolo ...

drostanolone enanthate Drostanolone, or dromostanolone, is an anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was never marketed. An androgen ester prodrug of drostanolone, drostanolone propionate, was formerly used in the treatment o ...

, and

methenolone enanthate Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It i ...

(Primobolan). The triglyceride ester of enanthic acid is the triheptanoin, which is used in certain medical conditions as a nutritional supplement.

Safety

Enanthic acid is toxic if swallowed and corrosive.

References

{{Fatty acids Alkanoic acids Fatty acids

Production

Uses

Safety

See also

References