Chemistry:Caprylic acid
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| Names | |
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| Preferred IUPAC name
Octanoic acid | |
| Other names
1-Heptanecarboxylic acid
Octylic acid Octoic acid C8:0 (lipid numbers) | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
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| KEGG | |
PubChem CID
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| Properties | |
| C8H16O2 | |
| Molar mass | 144.214 g/mol |
| Appearance | Oily colorless liquid |
| Odor | Faint, fruity-acid; irritating |
| Density | 0.910 g/cm3[1] |
| Melting point | 16.7 °C (62.1 °F; 289.8 K)[3] |
| Boiling point | 239.7 °C (463.5 °F; 512.8 K)[1] |
| 0.068 g/100 mL[1] | |
| Solubility | Soluble in alcohol, chloroform, ether, CS2, petroleum ether, acetonitrile |
| log P | 3.05 |
| Vapor pressure | 0.25 Pa |
| Acidity (pKa) |
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| −101.60·10−6 cm3/mol | |
Refractive index (nD)
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1.4285 |
| Thermochemistry | |
Heat capacity (C)
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297.9 J/K·mol |
Std enthalpy of
formation (ΔfH⦵298) |
−636 kJ/mol |
| Hazards | |
| GHS pictograms |  [4]
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| GHS Signal word | Danger |
| H314 | |
| P264, P280, P301+330+331, P303+361+353, P304+340+310, P305+351+338+310, P363, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 130 °C (266 °F; 403 K) |
| 440 °C (824 °F; 713 K) | |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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10.08 g/kg (orally in rats)[1] |
| Related compounds | |
Related compounds
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Heptanoic acid, nonanoic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Caprylic acid (from la capra 'goat'), 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 H
3C–(CH
2)
6–COOH, and is a colorless oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste.[1] Salts and esters of octanoic acid are known as octanoates or caprylates. It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde.[5] Its compounds are found naturally in the milk of various mammals and as a minor constituent of coconut oil and palm kernel oil.[3]
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.[citation needed]
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.[6]
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.[citation needed]
The acyl chloride of caprylic acid is used in the synthesis of perfluorooctanoic acid.[7]
Dietary uses
Caprylic acid is taken as a dietary supplement. In the body, caprylic acid would be found as octanoate, or unprotonated caprylic acid.[8]
Some studies have shown that medium-chain triglycerides (MCTs) can help in the process of excess calorie burning, and thus weight loss;[9][10][11][12][13] however, a systematic review of the evidence concluded that the overall results are inconclusive.[14] 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.[13]
Medical uses
Caprylic acid has been studied as part of a ketogenic diet to treat children with intractable epilepsy.[15] Caprylic acid is currently being researched as a treatment for essential tremor.[15][16]
See also
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Budavari, Susan, ed. (1996), An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
- ↑ Lide, D.R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
- ↑ 3.0 3.1 Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry 73 (4): 685–744. doi:10.1351/pac200173040685.
- ↑ Sigma-Aldrich Co., Octanoic acid. Retrieved on 2022-08-11.
- ↑ Riemenschneider, Wilhelm (2002). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235.
- ↑ EPA - Antimicrobials Division. Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.
- ↑ Savu, Patricia M. (2000). Kirk-Othmer Encyclopedia of Chemical Technology. p. 1. doi:10.1002/0471238961.0612211519012221.a01. ISBN 978-0-471-23896-6.
- ↑ PubChem. "Octanoic acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/379.
- ↑ B. Martena; M. Pfeuffer; J. Schrezenmeir (2006). "Medium-chain triglycerides". International Dairy Journal 16 (11): 1374–1382. doi:10.1016/j.idairyj.2006.06.015.
- ↑ Takeuchi, H; Sekine, S; Kojima, K; Aoyama, T (2008). "The application of medium-chain fatty acids: edible oil with a suppressing effect on body fat accumulation". Asia Pacific Journal of Clinical Nutrition 17 (Suppl 1): 320–3. PMID 18296368.
- ↑ St-Onge, MP; Jones, PJ (2002). "Physiological effects of medium-chain triglycerides: potential agents in the prevention of obesity". The Journal of Nutrition 132 (3): 329–32. doi:10.1093/jn/132.3.329. PMID 11880549.
- ↑ Papamandjaris, AA; MacDougall, DE; Jones, PJ (1998). "Medium chain fatty acid metabolism and energy expenditure: obesity treatment implications". Life Sciences 62 (14): 1203–15. doi:10.1016/S0024-3205(97)01143-0. PMID 9570335.
- ↑ 13.0 13.1 Clegg, M. E. (2010). "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. doi:10.3109/09637481003702114. PMID 20367215.
- ↑ "Influence of the dietary intake of medium chain triglycerides on body composition, energy expenditure and satiety: a systematic review". Nutr Hosp 27 (1): 103–108. 2012. doi:10.3305/nh.2012.27.1.5369. PMID 22566308.
- ↑ 15.0 15.1 Voller, Bernhard; Lines, Emily; McCrossin, Gayle; Tinaz, Sule; Lungu, Codrin; Grimes, George; Starling, Judith; Potti, Gopal et al. (2016-02-29). "Dose-escalation study of octanoic acid in patients with essential tremor" (in en). Journal of Clinical Investigation 126 (4): 1451–1457. doi:10.1172/JCI83621. ISSN 0021-9738. PMID 26927672.
- ↑ 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" (in en). The Laryngoscope 129 (8): 1882–1890. doi:10.1002/lary.27695. PMID 30585335.
External links
- Caprylic Acid Benefits – Caprylic Acid: Benefits & Side Effects
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