Caprylic acid
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 | |
ECHA InfoCard
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100.004.253 |
EC Number |
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IUPHAR/BPS |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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 (ΔfH⦵298)formation |
−636 kJ/mol |
Hazards | |
GHS labelling: | |
[4] | |
Danger | |
H314 | |
P264, P280, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, 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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nonanoic acid
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Caprylic acid (from
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
See also
References
- ^ ISBN 0911910123
- ^ Lide, D.R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
- ^ S2CID 84492006.
- ^ Sigma-Aldrich Co., Octanoic acid. Retrieved on 2022-08-11.
- ISBN 978-3527306732.
- ^ EPA - Antimicrobials Division. Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.
- ISBN 978-0-471-23896-6.
- ^ PubChem. "Octanoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-05-15.
- PMC 2020023.
- PMID 18296368.
- PMID 11880549.
- PMID 9570335.
- ^ S2CID 6128370.
- PMID 22566308.
- ^ PMID 26927672.
- PMID 30585335.
External links
- Caprylic Acid Benefits – Caprylic Acid: Benefits & Side Effects