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 . Carboxylate salt and of decanoic acid are called caprates or decanoates. The term capric acid is derived from the Latin " caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.
Occurrence
Capric acid occurs naturally in
coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils.
[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. ] It is found in the
milk of various mammals and to a lesser extent in other animal fats.
Two other acids are named after goats: caproic acid (a C6:0 fatty acid) and caprylic acid (a C8:0 fatty acid). Along with capric acid, these total 15% in goat milk fat.
Production
Capric acid can be prepared from
Redox of the primary alcohol decanol by using chromium trioxide ()
oxidizing agent under acidic conditions.
Neutralization of capric acid or saponification of its triglyceride esters with sodium hydroxide yields sodium caprate, . This salt is a component of some types of soap.
Uses
Capric acid is used in the manufacture of
Ester for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.
Pharmaceuticals
Caprate ester
of various pharmaceuticals are available. Since capric acid is a fatty acid, forming a salt or ester with a drug will increase its
lipophilicity and its affinity for
adipose tissue. Since distribution of a drug from
Adipose tissue is usually slow, one may develop a long-acting injectable form of a drug (called a
depot injection) by using its caprate form. Some examples of drugs available as a caprate ester include
nandrolone (as nandrolone decanoate),
(as fluphenazine decanoate),
(as bromperidol decanoate),
and
haloperidol (as haloperidol decanoate).
Effects
Capric acid acts as a non-competitive
AMPA receptor antagonist at therapeutically relevant concentrations, in a voltage- and subunit-dependent manner, and this is sufficient to explain its
Seizure effects.
This direct inhibition of excitatory neurotransmission by capric acid in the brain contributes to the
anticonvulsant effect of the MCT
ketogenic diet.
[ Decanoic acid and the AMPA receptor antagonist drug perampanel act at separate sites on the AMPA receptor, and so it is possible that they have a cooperative effect at the AMPA receptor, suggesting that perampanel and the ketogenic diet could be synergistic.][
]
Capric acid may be responsible for the mitochondrial proliferation associated with the ketogenic diet, and that this may occur via PPARγ receptor agonism and its target genes involved in mitochondrial biogenesis.
It should however be noted that orally ingested medium chain fatty acids would be very rapidly degraded by first-pass metabolism by being taken up in the liver via the portal vein, and are quickly metabolized via coenzyme A intermediates through β-oxidation and the citric acid cycle to produce carbon dioxide, acetate and ketone bodies.
See also
