Capric acid explained

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 acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.[1]

Occurrence

Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils.[2] 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.[3]

Production

Capric acid can be prepared from oxidation of the primary alcohol decanol by using chromium trioxide oxidant under acidic conditions.[4]

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 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.[5]

Pharmaceuticals

Caprate ester prodrugs 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 fatty 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),[6] fluphenazine (as fluphenazine decanoate),[7] bromperidol (as bromperidol decanoate),[8] 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 antiseizure effects.[9] This direct inhibition of excitatory neurotransmission by capric acid in the brain contributes to the anticonvulsant effect of the MCT ketogenic diet.[9] 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.[9]

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.[10] [11] Complex I activity of the electron transport chain is substantially elevated by decanoic acid treatment.

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.[12] Whether the ketones, β-hydroxybutyrate and acetone have direct antiseizure activity is unclear.[9] [13] [14] [15]

See also

Notes and References

  1. Web site: capri-, capr- +. 2012-09-28. 2017-12-23. https://web.archive.org/web/20171223161349/http://wordinfo.info/unit/371. live.
  2. 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.
  3. Hilditch . T. P. . Jasperson . H. . The component acids of milk fats of the goat, ewe and mare . Biochemical Journal . 1944 . 38 . 5 . 443–447 . 10.1042/bj0380443 . 16747831 . 1258125 .
  4. Book: McMurry, John . Organic Chemistry . 7th . Thompson - Brooks/Cole . 2008 . 624 . John E. McMurry.
  5. Web site: CAPRIC ACID . AroKor Holdings . chemicalland21.com . 2014-06-15 . 2018-10-19 . https://web.archive.org/web/20181019110735/http://chemicalland21.com/industrialchem/organic/CAPRIC . live .
  6. Web site: ROLON 250mg/ml Solution for Injection - Summary of Product Characteristics (SmPC) - (emc) . https://web.archive.org/web/20200922210716/https://www.medicines.org.uk/emc/product/5374/smpc#gref . 2020-09-22 . 2020-10-09 . www.medicines.org.uk.
  7. Web site: fluphenazine decanoate . live . https://web.archive.org/web/20151208191534/http://www.drugs.com/monograph/fluphenazine-decanoate.html . 8 December 2015 . 1 December 2015 . The American Society of Health-System Pharmacists.
  8. Book: The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . 14 November 2014 . Springer . 978-1-4757-2085-3 . J. Elks . 182– . 1058412474.
  9. Chang . Pishan . Augustin . Katrin . Boddum . Kim . Williams . Sophie . Sun . Min . Terschak . John A. . Hardege . Jörg D. . Chen . Philip E. . Walker . Matthew C. . Williams . Robin S. B. . Seizure control by decanoic acid through direct AMPA receptor inhibition . Brain . February 2016 . 139 . 2 . 431–443 . 10.1093/brain/awv325 . 4805082 . 26608744 .
  10. Hughes . Sean David . Kanabus . Marta . Anderson . Glenn . Hargreaves . Iain P. . Rutherford . Tricia . Donnell . Maura O’ . Cross . J. Helen . Rahman . Shamima . Eaton . Simon . Heales . Simon J. R. . The ketogenic diet component decanoic acid increases mitochondrial citrate synthase and complex I activity in neuronal cells . Journal of Neurochemistry . May 2014 . 129 . 3 . 426–433 . 10.1111/jnc.12646 . 24383952 . 206089968 . free .
  11. Malapaka . Raghu R. V. . Khoo . SokKean . Zhang . Jifeng . Choi . Jang H. . Zhou . X. Edward . Xu . Yong . Gong . Yinhan . Li . Jun . Yong . Eu-Leong . Chalmers . Michael J. . Chang . Lin . Resau . James H. . Griffin . Patrick R. . Chen . Y. Eugene . Xu . H. Eric . Identification and Mechanism of 10-Carbon Fatty Acid as Modulating Ligand of Peroxisome Proliferator-activated Receptors . Journal of Biological Chemistry . 2 January 2012 . 287 . 1 . 183–195 . 10.1074/jbc.M111.294785 . 22039047 . 3249069 . free .
  12. Chang . Pishan . Terbach . Nicole . Plant . Nick . Chen . Philip E. . Walker . Matthew C. . Williams . Robin S.B. . Seizure control by ketogenic diet-associated medium chain fatty acids . Neuropharmacology . June 2013 . 69 . 105–114 . 10.1016/j.neuropharm.2012.11.004 . 23177536 . 3625124 .
  13. Viggiano . Andrea . Pilla . Raffaele . Arnold . Patrick . Monda . Marcellino . D׳Agostino . Dominic . Coppola . Giangennaro . Anticonvulsant properties of an oral ketone ester in a pentylenetetrazole-model of seizure . Brain Research . August 2015 . 1618 . 50–54 . 10.1016/j.brainres.2015.05.023 . 26026798 .
  14. Rho . Jong M. . Anderson . Gail D. . Donevan . Sean D. . White . H. Steve . Acetoacetate, Acetone, and Dibenzylamine (a Contaminant in l-(+)-β-Hydroxybutyrate) Exhibit Direct Anticonvulsant Actions in Vivo . Epilepsia . 22 April 2002 . 43 . 4 . 358–361 . 10.1046/j.1528-1157.2002.47901.x . 11952765 . 31196417 .
  15. Ma . Weiyuan . Berg . Jim . Yellen . Gary . Ketogenic Diet Metabolites Reduce Firing in Central Neurons by Opening KATP Channels . The Journal of Neuroscience . 4 April 2007 . 27 . 14 . 3618–3625 . 10.1523/JNEUROSCI.0132-07.2007 . 17409226 . 6672398 .

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