Caprylic acid

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Caprylic acid
Skeletal formula
Ball-and-stick model
IUPAC name
octanoic acid
Other names
124-07-2 YesY
ChEBI CHEBI:28837 YesY
ChEMBL ChEMBL324846 YesY
ChemSpider 370 YesY
DrugBank DB04519 YesY
EC Number 204-677-5
Jmol interactive 3D Image
KEGG D05220 YesY
PubChem 379
Molar mass 144.21 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)[5]
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) 4.89[2]


297.9 J/K mol
-636 kJ/mol
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazard COR: Corrosive; strong acid or base. E.g., sulfuric acid, potassium hydroxideNFPA 704 four-colored diamond
Flash point 130 °C (266 °F; 403 K)
440 °C (824 °F; 713 K)
Lethal dose or concentration (LD, LC):
10.08 g/kg (orally in rats)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. Its compounds are found naturally in the milk of various mammals, and as a minor constituent of coconut oil and palm kernel oil.[5] It is an oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste.[1]

Two other acids are named after goats: caproic (C6) and capric (C10). Along with caprylic acid these total 15% in goat milk fat.


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

It has been observed that Malonyl-CoA inhibits palmitic acid oxidation in isolated mitochondria, but that it has little or no effect on the oxidation of octanoic acid (C8, Saturated). This observation can be explained by AMP functions serving as an energy sensor and regulator of metabolism. When ATP production does not keep up with needs, a higher portion of a cell's adenine nucleotide pool is in the form of AMP. AMP promotes catabolic pathways that lead to synthesis of ATP, while inhibiting energy-utilizing synthetic pathways. For example, AMP regulates fatty acid synthesis and catabolism by controlling availability of malonyl-CoA.

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, schools/colleges, animal care/veterinary facilities, industrial facilities, office buildings, recreational facilities, retail and wholesale establishments, livestock premises, restaurants, and hotels/motels. In addition, caprylic acid is used as an algaecide, bactericide, and fungicide in nurseries, greenhouses, garden centers, and interiorscapes on ornamentals. Products containing caprylic acid are formulated as soluble concentrate/liquids and ready-to-use liquids.[6]

For ghrelin to have a hunger-stimulating action on a hypothalamus, caprylic acid must be linked to a serine residue at the 3-position of ghrelin. To cause hunger, it must acylate an -OH group. Other fatty acids in the same position have similar effects on hunger.

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

Dietary uses[edit]

Caprylic acid is taken as a dietary supplement.

Some studies have shown that medium-chain triglycerides (MCTs) can help in the process of excess calorie burning, and thus weight loss.[7][8][9][10] MCTs are also seen as promoting fat oxidation and reduced food intake.[11] There has also been interest in MCTs from endurance athletes and the bodybuilding community.[12]

It is believed to suppress fungal infections within the gut, notably candida albicans infection.[13]


  1. ^ a b c d e Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123 
  2. ^ Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press. 
  3. ^ at 2.06–2.63 K
  4. ^ at −191 °C
  5. ^ a b 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. 
  6. ^ EPA - Antimicrobials Division. Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.
  7. ^ 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. 
  8. ^ 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. 
  9. ^ 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. PMID 11880549. 
  10. ^ 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. 
  11. ^ 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. 
  12. ^ Talbott, Shawn M. and Kerry Hughes. (2006). The Health Professional's Guide to Dietary Supplements. Lippincott Williams & Wilkins. pp. 60–63. ISBN 978-0-7817-4672-4.
  13. ^ Omura, Y; O'Young, B; Jones, M; Pallos, A; Duvvi, H; Shimotsuura, Y (2011). "Caprylic acid in the effective treatment of intractable medical problems of frequent urination, incontinence, chronic upper respiratory infection, root canalled tooth infection, ALS, etc., caused by asbestos & mixed infections of Candida albicans, Helicobacter pylori & cytomegalovirus with or without other microorganisms & mercury". Acupuncture & electro-therapeutics research 36 (1–2): 19–64. doi:10.3727/036012911803860886. PMID 21830350.