Caprylic acid

Caprylic acid
IUPAC name octanoic acid
Other names C8:0 (Lipid numbers)
Identifiers
CAS number	124-07-2 Y
PubChem	379
ChemSpider	370 Y
UNII	OBL58JN025 Y
EC number	204-677-5
DrugBank	DB04519
KEGG	D05220 Y
ChEBI	CHEBI:28837 Y
ChEMBL	CHEMBL324846 Y
Jmol-3D images	Image 1
SMILES CCCCCCCC(=O)O
InChI InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) Y Key: WWZKQHOCKIZLMA-UHFFFAOYSA-N Y InChI=1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) Key: WWZKQHOCKIZLMA-UHFFFAOYAH
Properties
Molecular formula	C8H16O2
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 ([2])
Boiling point	239.7 °C; 463.5 °F; 512.8 K ([1])
Solubility in water	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[3] 1.055[4] 1.53[5]
Refractive index (nD)	1.4285
Thermochemistry
Std enthalpy of formation ΔfHo298	-636 kJ/mol
Specific heat capacity, C	297.9 J/K mol
Hazards
NFPA 704	0 3 1 COR
Flash point	130 °C; 266 °F; 403 K
Autoignition temperature	440 °C; 824 °F; 713 K
LD50	10.08 g/kg (orally in rats)[1]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.^[2] 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.^[6]

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.^[7]

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 a -OH group. Other fatty acids in the same position have similar effects on hunger.

The octanoic acid breath test is used to measure gastric emptying. Some potential benefit is possible from administration of octanoic acid for patients with essential tremor.

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

Caprylic acid is taken as a dietary supplement within alternative medicine. It is believed to suppress fungal infections within the gut, notably candida albicans infection.

References