Capric acid, also known as decanoic acidordecylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called capratesordecanoates. The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.[9]
Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils.[10] It is found in the milk of various mammals and to a lesser extent in other animal fats.[6]
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.[11]
Capric acid is used in the manufacture of esters 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.[8]
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 antiseizure effects.[16] This direct inhibition of excitatory neurotransmission by capric acid in the brain contributes to the anticonvulsant effect of the MCTketogenic diet.[16] 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.[16]
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.[19] Whether the ketones, β-hydroxybutyrate and acetone have direct antiseizure activity is unclear.[16][20][21][22]
^ abcn-Decanoic acid in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-06-15)
^ abcD. Bond, Andrew (2004). "On the crystal structures and melting point alternation of the n -alkyl carboxylic acids". New Journal of Chemistry. 28 (1): 104–114. doi:10.1039/B307208H.
^ abc"CAPRIC ACID". chemicalland21.com. AroKor Holdings. Archived from the original on 2018-10-19. Retrieved 2014-06-15.
^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. doi:10.1002/14356007.a10_245.pub2
^"fluphenazine decanoate". The American Society of Health-System Pharmacists. Archived from the original on 8 December 2015. Retrieved 1 December 2015.
^Viggiano, Andrea; Pilla, Raffaele; Arnold, Patrick; Monda, Marcellino; D׳Agostino, Dominic; Coppola, Giangennaro (August 2015). "Anticonvulsant properties of an oral ketone ester in a pentylenetetrazole-model of seizure". Brain Research. 1618: 50–54. doi:10.1016/j.brainres.2015.05.023. PMID26026798.
^Rho, Jong M.; Anderson, Gail D.; Donevan, Sean D.; White, H. Steve (22 April 2002). "Acetoacetate, Acetone, and Dibenzylamine (a Contaminant in l-(+)-β-Hydroxybutyrate) Exhibit Direct Anticonvulsant Actions in Vivo". Epilepsia. 43 (4): 358–361. doi:10.1046/j.1528-1157.2002.47901.x. PMID11952765. S2CID31196417.
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