Caprylic acid explained

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. Salts and esters of octanoic acid are known as octanoates or caprylates. The name of the related acyl group is octanoyl, capryloyl, or caprylyl.[1] 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.

Uses

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

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. In addition, 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.[2]

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.

The acyl chloride of caprylic acid is used in the synthesis of perfluorooctanoic acid.[3]

Dietary uses

Caprylic acid is taken as a dietary supplement. In the body, caprylic acid would be found as octanoate, or unprotonated caprylic acid.[4]

Some studies have shown that medium-chain triglycerides (MCTs) can help in the process of excess calorie burning, and thus weight loss;[5] [6] [7] [8] [9] however, a systematic review of the evidence concluded that the overall results are inconclusive.[10] Also, interest in MCTs has been shown by endurance athletes and the bodybuilding community, but MCTs have not been found to be beneficial to exercise performance.[9]

Medical uses

Caprylic acid has been studied as part of a ketogenic diet to treat children with intractable epilepsy. Caprylic acid is currently being researched as a treatment for essential tremor.[11] [12]

See also

External links

Notes and References

  1. Web site: CHEBI:25650 - octanoyl group. Chemical Entities of Biological Interest (ChEBI). 23 November 2010. 4 July 2024.
  2. EPA - Antimicrobials Division. Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.
  3. Encyclopedia: 10.1002/0471238961.0612211519012221.a01 . Fluorinated Higher Carboxylic Acids . . 2000 . Savu . Patricia M. . 1 . 978-0-471-23896-6.
  4. Web site: Octanoic acid. PubChem. pubchem.ncbi.nlm.nih.gov. en. 2019-05-15.
  5. Medium-chain triglycerides. B. Martena . M. Pfeuffer . J. Schrezenmeir . International Dairy Journal . 16. 11. 2006. 1374–1382 . 10.1016/j.idairyj.2006.06.015. 2020023.
  6. Takeuchi . H . Sekine . S . Kojima . K . Aoyama . T . The application of medium-chain fatty acids: edible oil with a suppressing effect on body fat accumulation . Asia Pacific Journal of Clinical Nutrition . 17 . 320–3 . 2008 . Suppl 1 . 18296368.
  7. St-Onge . MP . Jones . PJ . Physiological effects of medium-chain triglycerides: potential agents in the prevention of obesity . The Journal of Nutrition . 132 . 3 . 329–32 . 2002 . 11880549. 10.1093/jn/132.3.329 . free .
  8. Papamandjaris . AA . MacDougall . DE . Jones . PJ . Medium chain fatty acid metabolism and energy expenditure: obesity treatment implications . Life Sciences . 62 . 14 . 1203–15 . 1998 . 9570335 . 10.1016/S0024-3205(97)01143-0.
  9. Clegg . M. E. . Medium-chain triglycerides are advantageous in promoting weight loss although not beneficial to exercise performance . International Journal of Food Sciences and Nutrition . 61 . 7 . 653–679 . 2010 . 20367215 . 10.3109/09637481003702114. 6128370 .
  10. Nutr Hosp . 2012 . 27 . 1 . 103–108 . 10.3305/nh.2012.27.1.5369 . Influence of the dietary intake of medium chain triglycerides on body composition, energy expenditure and satiety: a systematic review . Rego Costa AC, Rosado EL, Soares-Mota M . 22566308.
  11. Voller. Bernhard. Lines. Emily. McCrossin. Gayle. Tinaz. Sule. Lungu. Codrin. Grimes. George. Starling. Judith. Potti. Gopal. Buchwald. Peter. 2016-02-29. Dose-escalation study of octanoic acid in patients with essential tremor. Journal of Clinical Investigation. en. 126. 4. 1451–1457. 10.1172/JCI83621. 26927672. 0021-9738. 4811161.
  12. Lowell. Soren Y.. Kelley. Richard T.. Monahan. Marika. Hosbach-Cannon. Carly Jo. Colton. Raymond H.. Mihaila. Dragos. 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. 129. 8. 1882–1890. en. 10.1002/lary.27695. 30585335. 6592780.