Caprylic acid


Caprylic acid
Caprylic acid
Identifiers
CAS number 124-07-2 YesY
PubChem 379
ChemSpider 370 YesY
UNII OBL58JN025 YesY
DrugBank DB04519
KEGG D05220 YesY
ChEBI CHEBI:28837 YesY
ChEMBL CHEMBL324846 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H16O2
Molar mass 144.21 g/mol
Appearance Oily colorless liquid
Density 0.910 g/cm3[1]
Melting point

16.7 °C, 290 K, 62 °F ([3])

Boiling point

239.7 °C, 513 K, 463 °F ([1])

Solubility in water 0.68 g/100 mL[1]
Acidity (pKa) 4.89[2]
Hazards
LD50 10.08 g/kg (orally in rats)[1]
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. It is found naturally in the milk of various mammals, and it is a minor constituent of coconut oil and palm kernel oil.[3] 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.

Uses

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

Caprylic acid is also used in the treatment of some bacterial infections. Due to its relatively short chain length it has no difficulty in penetrating fatty cell wall membranes, hence its effectiveness in combating certain lipid-coated bacteria, such as Staphylococcus aureus and various species of Streptococcus.[4]

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.[5]

Caprylic acid must be covalently linked to the serine residue at the 3-position of ghrelin, specifically, it must acylate the -OH group, for ghrelin to have its hunger-stimulating action on the feeding centers of the hypothalamus, though other fatty acids may have similar effects.[clarification needed]

The octanoic acid breath test is used to measure gastric emptying.

References

  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. ^ 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. http://iupac.org/publications/pac/73/4/0685/. 
  4. ^ Nair MK, Joy J, Vasudevan P, Hinckley L, Hoagland TA, Venkitanarayanan KS (Oct 2005). "Antibacterial effect of caprylic acid and monocaprylin on major bacterial mastitis pathogens". J Dairy Sci 88 (10): 3488–95. doi:10.3168/jds.S0022-0302(05)73033-2. PMID 16162522. 
  5. ^ EPA - Antimicrobials Division - www.regulations.gov - Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.

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