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Caprylic acid

Fatty acid (CH3–(CH2)6–COOH)

Summary

Fatty acid (CH3–(CH2)6–COOH)

Octylic acid Octoic acid C8:0 (lipid numbers) |4.89 |1.055 (2.06–2.63 K) |1.53 (−191 °C) |NFPA-H = 3 | NFPA-F = 0 | NFPA-R = 1 | NFPA-S = COR

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 a slightly unpleasant rancid-like smell and taste. It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde. Its compounds are found naturally in the milk of various mammals and as a minor constituent of coconut oil and palm kernel oil.

Two other acids are named after goats via the Latin word capra: caproic acid (C6) and capric acid (C10). Together, these three fatty acids comprise 15% of the fatty acids in goat milk fat.

Metabolism

Octanoyl-mtACP ===

One of the products of the mitochondrial fatty acid synthesis (mtFAS) pathway is octanoic acid bound to the mitochondrial acyl carrier protein (mtACP), also referred to as octanoyl-mtACP. In the absence of a mitochondrial acyl-mtACP thioesterase—none has been identified in any animal species—octanoic acid remains attached to mtACP rather than being released as a free fatty acid. Octanoyl-mtACP serves as the precursor for the biosynthesis of lipoic acid, a vital cofactor required by several key mitochondrial enzymes complexes, including the pyruvate dehydrogenase complex (PDC), the α‑ketoglutarate dehydrogenase complex (OGDC), the 2-oxoadipate dehydrogenase complex (OADHC), the branched‑chain α‑ketoacid dehydrogenase complex (BCKDC), and the glycine cleavage system (GCS).

Octanoyl-CoA

Main article: Octanoyl-CoA

Caprylic acid plays an important role in the body's regulation of energy input and output, a function which is performed by the hormone ghrelin. The sensation of hunger is a signal that the body requires an input of energy in the form of food consumption. Ghrelin stimulates hunger by triggering receptors in the hypothalamus. In order to activate these receptors, ghrelin must undergo a process called acylation in which it acquires an acyl group, and caprylic acid provides this by linking at a specific serine site on ghrelin molecules. Other fatty acids in the same position have similar effects on hunger.

Uses

Industrial and commercial use

Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes.

The acyl chloride of caprylic acid is used in the synthesis of perfluorooctanoic acid.

Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer in commercial food handling establishments on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities and public places. Caprylic acid is used as an algicide, bactericide, fungicide, and herbicide in nurseries, greenhouses, garden centers, and interiors, and on ornamentation. Products containing caprylic acid are formulated as soluble concentrate/liquids and ready-to-use liquids.

Dietary uses

Caprylic acid is taken as a dietary supplement. In the body, caprylic acid would be found as octanoate, or unprotonated caprylic acid.

Some studies have shown that medium-chain triglycerides (MCTs) can help in the process of excess calorie burning, and thus weight loss;{{Cite journal | doi-access = free

Medical uses

Caprylic acid has been studied as part of a ketogenic diet to treat children with intractable epilepsy. Caprylic acid is being researched as a treatment for essential tremor.

References

References

  1. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry.
  2. {{Merck12th
  3. Lide, D.R. (Ed.). (1990). "CRC Handbook of Chemistry and Physics (70th Edn.)". Boca Raton (FL):CRC Press.
  4. {{Sigma-Aldrich
  5. (23 November 2010). "CHEBI:25650 - octanoyl group". Chemical Entities of Biological Interest (ChEBI).
  6. (2002). "Carboxylic Acids, Aliphatic".
  7. (October 2018). "Impact of Mitochondrial Fatty Acid Synthesis on Mitochondrial Biogenesis". Current Biology.
  8. (2024-01-02). "Mitochondrial fatty acid synthesis is an emergent central regulator of mammalian oxidative metabolism". Cell Metabolism.
  9. (February 2018). "Protein lipoylation: an evolutionarily conserved metabolic regulator of health and disease". Current Opinion in Chemical Biology.
  10. (May 2018). "Lipoic acid metabolism and mitochondrial redox regulation". Journal of Biological Chemistry.
  11. {{cite encyclopedia. (2000)
  12. EPA - Antimicrobials Division. [http://www.regulations.gov/#!docketDetail;D=EPA-HQ-OPP-2008-0477 Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid].
  13. PubChem. "Octanoic acid".
  14. (2006). "Medium-chain triglycerides". International Dairy Journal.
  15. (2012). "Influence of the dietary intake of medium chain triglycerides on body composition, energy expenditure and satiety: a systematic review". Nutr Hosp.
  16. (2016-02-29). "Dose-escalation study of octanoic acid in patients with essential tremor". Journal of Clinical Investigation.
  17. (2018-12-25). "The Effect of Octanoic Acid on Essential Voice Tremor: A Double-Blind, Placebo-Controlled Study: Effect of Octanoic Acid on EVT". The Laryngoscope.
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

antifungals alkanoic-acids biologically-based-therapies fatty-acids
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