Enanthic acid, also called heptanoic acid, is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
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 Substituent, R-group. The general formula of a carboxylic acid is often written as or , sometimes as with R referring to an organyl ...
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
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
and ether. Salts
In chemistry, a salt or ionic compound is a chemical compound consisting of an assembly of positively charged ions ( cations) and negatively charged ions (anions), which results in a compound with no net electric charge (electrically neutral). ...
and ester
In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s of enanthic acid are called enanthates or heptanoates.
Its name derives from the Latin
Latin ( or ) is a classical language belonging to the Italic languages, Italic branch of the Indo-European languages. Latin was originally spoken by the Latins (Italic tribe), Latins in Latium (now known as Lazio), the lower Tiber area aroun ...
'' oenanthe'' which is in turn derived from the Ancient Greek
Ancient Greek (, ; ) includes the forms of the Greek language used in ancient Greece and the classical antiquity, ancient world from around 1500 BC to 300 BC. It is often roughly divided into the following periods: Mycenaean Greek (), Greek ...
''oinos'' "wine" and ''anthos'' "blossom."
Production
The methyl ester of ricinoleic acid
Ricinoleic acid, formally called 12-hydroxy-9-''cis''-octadecenoic acid, is a fatty acid. It is an Unsaturated fatty acid, unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from the seeds of casto ...
, obtained from castor bean oil
Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant ''Ricinus communis''. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its de ...
, is the main commercial precursor to enanthic acid. It is pyrolyzed to the methyl ester of 10-undecenoic acid 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 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 ...
and 1-octene.
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 (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an ...
, 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 is used in the treatment of low testosterone levels in men. It is also used in hormone therapy for women and transgender men. It is given by injection into muscle or subcutaneously usually once every one to four weeks. ...
, 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 ...
, 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 ...
(Primobolan).
The triglyceride
A triglyceride (from '' tri-'' and '' glyceride''; also TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids.
Triglycerides are the main constituents of body fat in humans and other vertebrates ...
ester of enanthic acid is the triheptanoin
Triheptanoin, sold under the brand name Dojolvi, is a medication for the treatment of children and adults with molecularly confirmed long-chain fatty acid oxidation disorders (LC-FAOD).
The most common adverse reactions include abdominal pain, ...
, which is used in certain medical conditions as a nutritional supplement.
Safety
Enanthic acid is corrosive.[
]
See also
* List of saturated fatty acids
Saturated fatty acids are fatty acids that make up saturated fats.
Straight-chain
Saturated straight-chain fatty acids:
Branched-chain
Saturated branched-chain fatty acids:
See also
*List of unsaturated fatty acids
*Carboxylic acid
...
* List of carboxylic acids
Carboxylic acids are organic acids characterized by a carboxyl (-COOH) functional group. The naming of these compounds is governed by IUPAC nomenclature, which ensures systematic and consistent naming of chemicals. Numerous organic compounds have ...
References
{{Fatty acids
Alkanoic acids
Fatty acids