Caprylic acid
| File:Caprylic acid.png | |
| Names | |
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| IUPAC name
octanoic acid
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.004.253 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C8H16O2 | |
| Molar mass | 144.21144 |
| Density | 0.910 g/cm3 |
| Melting point | 16-17 °C |
| Boiling point | 237 °C |
| Acidity (pKa) | 4.89[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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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 coconuts and breast milk. It is an oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell.
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, aka, octanoic 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.
References
- ^ Lide, D. R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
- ^ at 2.06–2.63 K
- ^ at −191 °C
- ^ Nair MK, Joy J, Vasudevan P, Hinckley L, Hoagland TA, Venkitanarayanan KS. Antibacterial effect of caprylic acid and monocaprylin on major bacterial mastitis pathogens. J Dairy Sci. 2005 Oct;88(10):3488-95.