Decanoic acid, or capric acid, is a saturated fatty acid

Fatty acid

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid with a long unbranched aliphatic tail , which is either saturated or unsaturated. Most naturally occurring fatty acids have a chain of an even number of carbon atoms, from 4 to 28. Fatty acids are usually derived from...

.
Its formula is CH₃(CH₂)₈COOH. Salts and ester

Ester

Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...

s of decanoic acid are called decanoates. The term capric acid arises from the Latin "capric" which pertains to goats due to their olfactory similarities.

Capric acid occurs naturally in coconut oil

Coconut oil

Coconut oil is an edible oil extracted from the kernel or meat of matured coconuts harvested from the coconut palm . Throughout the tropical world, it has provided the primary source of fat in the diets of millions of people for generations. It has various applications in food, medicine, and industry...

 and palm kernel oil

Palm kernel oil

Palm kernel oil is an edible plant oil derived from the kernel of the oil palm Elaeis guineensis. It should not be confused with the other two edible oils derived from palm fruits: coconut oil, extracted from the kernel of the coconut, and palm oil, extracted from the pulp of the oil palm...

, as well as in the milk

Milk

Milk is a white liquid produced by the mammary glands of mammals. It is the primary source of nutrition for young mammals before they are able to digest other types of food. Early-lactation milk contains colostrum, which carries the mother's antibodies to the baby and can reduce the risk of many...

 of various mammals and to a lesser extent in other animal fats.

It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.

Two other acids are named after goats: caproic (C6) and caprylic

Caprylic acid

Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. It is found naturally in the milk of various mammals, and it is a minor constituent of coconut oil and palm kernel oil...

 (C8). Along with decanoic acid, these total 15% in goat milk fat.

Production

Decanoic acid can be prepared from oxidation of primary alcohol

Primary

The word Primary when used alone may refer to any of the following:* Primary , the larger of two co-orbiting bodies* Primary is used for the name of the primary mirror in a telescope.* Primary , from Australia...

 decanol, by using chromium trioxide

Chromium trioxide

Chromium trioxide is the inorganic compound with the formula CrO3. It is the acidic anhydride of chromic acid, and is sometimes marketed under the same name.This compound is a dark-red/orange brown solid, which dissolves in water concomitant with hydrolysis...

 (CrO₃) oxidant under acidic conditions in an acetone

Acetone

Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

 solvent. This will give decanoic acid in up to 93% yield.

Pharmaceuticals

Decanoate salts and esters of various drugs are available. Since decanoic acid is a fatty acid, forming a salt or ester with a drug will increase its lipophilicity and its affinity for fatty tissue. Since distribution

Distribution (pharmacology)

Distribution in pharmacology is a branch of pharmacokinetics which describes the reversible transfer of drug from one location to another within the body....

 of a drug from fatty tissue is usually slow, one may develop a long-acting injectable form of a drug (called a Depot injection) by using its decanoate form. Some examples of drugs available as a decanoate ester or salt include nandrolone

Nandrolone

Nandrolone is an anabolic steroid that may be present naturally in the human body, albeit in minute quantities of less than 0.4 ng/ml. Nandrolone is most commonly sold commercially as its decanoate ester and less commonly as a phenylpropionate ester...

, fluphenazine

Fluphenazine

Fluphenazine is a typical antipsychotic drug used for the treatment of psychoses such as schizophrenia and acute manic phases of bipolar disorder. It belongs to the piperazine class of phenothiazines....

, bromperidol

Bromperidol

Bromperidol is a drug which is a butyrophenone derivative. It is a potent and long-acting neuroleptic, used as an antipsychotic in the treatment of schizophrenia. It was discovered at Janssen Pharmaceutica in 1966.- References :...

, haloperidol

Haloperidol

Haloperidol is a typical antipsychotic. It is in the butyrophenone class of antipsychotic medications and has pharmacological effects similar to the phenothiazines....

 and vanoxerine

Vanoxerine

Vanoxerine is a piperazine derivative which is a potent and selective DRI. GBR-12909 binds to the target site on the DAT ~ 500 times more strongly than cocaine, but simultaneously inhibits the release of dopamine...

.

Use

Manufacturing of esters for artificial fruit flavors and perfumes. Also as an intermediate in chemical syntheses.