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Octanoic acid

Caprylic acid
Skeletal formula
Ball-and-stick model
Names
IUPAC name
octanoic acid
Other names
Identifiers
124-07-2 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:28837 YesY
ChEMBL ChEMBL324846 YesY
ChemSpider 370 YesY
DrugBank DB04519 YesY
ECHA InfoCard 100.004.253
EC Number 204-677-5
4585
KEGG D05220 YesY
PubChem 379
UNII OBL58JN025 YesY
Properties
C8H16O2
Molar mass 144.21 g·mol−1
Appearance Oily colorless liquid
Odor faint, fruity-acid; irritating
Density 0.910 g/cm3
Melting point 16.7 °C (62.1 °F; 289.8 K)
Boiling point 239.7 °C (463.5 °F; 512.8 K)
0.068 g/100 mL
Solubility soluble in alcohol, chloroform, ether, CS2, petroleum ether, acetonitrile
log P 3.05
Vapor pressure 0.25 Pa
Acidity (pKa) 4.89

1.055
1.53

-101.60·10−6 cm3/mol
1.4285
Thermochemistry
297.9 J/K mol
-636 kJ/mol
Hazards
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):
LD50 (median dose)
10.08 g/kg (orally in rats)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

1.055
1.53

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. It is an oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste.

Two other acids are named after goats via the Latin word : caproic acid (C6) and capric acid (C10). Along with caprylic acid (C8) 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.

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.

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.

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; however, a systematic review of the evidence concluded that the overall results are inconclusive. There has also been interest in MCTs from endurance athletes and the bodybuilding community, but MCTs are not beneficial to improved exercise performance.


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