Caproic acid, also known as hexanoic acid, is the

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 ...

derived from

hexane Hexane () or ''n''-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C6H14. Hexane is a colorless liquid, odorless when pure, and with a boiling point of approximately . It is widely used as ...

with the chemical formula . It is a colorless oily liquid with a fatty, cheesy, waxy odor resembling that of

goat The goat or domestic goat (''Capra hircus'') is a species of Caprinae, goat-antelope that is mostly kept as livestock. It was domesticated from the wild goat (''C. aegagrus'') of Southwest Asia and Eastern Europe. The goat is a member of the ...

s or other barnyard

animal Animals are multicellular, eukaryotic organisms in the Biology, biological Kingdom (biology), kingdom Animalia (). With few exceptions, animals heterotroph, consume organic material, Cellular respiration#Aerobic respiration, breathe oxygen, ...

s. It is a

fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...

found naturally in various animal

fat In nutrition science, nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such chemical compound, compounds, most commonly those that occur in living beings or in food. The term often refers specif ...

s and

oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) and lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturate ...

s, and is one of the chemicals that gives the decomposing fleshy seed coat of the

ginkgo ''Ginkgo'' is a genus of non-flowering seed plants, assigned to the gymnosperms. The scientific name is also used as the English common name. The order to which the genus belongs, Ginkgoales, first appeared in the Permian, , and ''Ginkgo'' is n ...

its characteristic unpleasant odor. It is also one of the components of

vanilla Vanilla is a spice derived from orchids of the genus ''Vanilla (genus), Vanilla'', primarily obtained from pods of the flat-leaved vanilla (''Vanilla planifolia, V. planifolia''). ''Vanilla'' is not Autogamy, autogamous, so pollination ...

and

cheese Cheese is a type of dairy product produced in a range of flavors, textures, and forms by coagulation of the milk protein casein. It comprises proteins and fat from milk (usually the milk of cows, buffalo, goats or sheep). During prod ...

. The primary use of caproic acid is in the manufacture of its

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 for use as artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols.

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

s of caproic acid are known as caproates or hexanoates. Several

progestin A progestogen, also referred to as a progestagen, gestagen, or gestogen, is a type of medication which produces effects similar to those of the natural female sex hormone progesterone in the body. A progestin is a '' synthetic'' progestogen. ...

medications are caproate esters, such as

hydroxyprogesterone caproate Hydroxyprogesterone caproate, sold under the brand name Delalutin among others, is a medication used to reduce the risk of preterm birth in women pregnant with one baby who have a history of spontaneous preterm birth. In March 2023, the manuf ...

and

gestonorone caproate Gestonorone caproate, also known as gestronol hexanoate or norhydroxyprogesterone caproate and sold under the brand names Depostat and Primostat, is a progestin medication which is used in the treatment of benign prostatic hyperplasia, enlarged p ...

. Two other acids are named after goats:

caprylic acid Caprylic acid (), also known under the systematic name octanoic acid or C8 Acid, is a saturated fatty acid, medium-chain fatty acid (MCFA). It has the structural formula , and is a colorless oily liquid that is minimally soluble in water with ...

(C8) and

capric acid Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is . Salts and esters of decanoic acid are called caprates or decanoates. The term capric aci ...

(C10). Along with caproic acid, they account for 15% of the fat in goat's milk. Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other two are mobile liquids) are not only used for the formation of esters, but also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.

References

{{Authority control Fatty acids Alkanoic acids

See also

References