Caprylic acid

Caprylic acid (from the Latin word capra, meaning "goat"), also known under the systematic name octanoic acid, is a saturated fatty acid and carboxylic acid with the structural formula CH3(CH2)6CO2H. It is a colorless oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste.[1] Salts and esters of octanoic acid are known as octanoates or caprylates. It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde.[4] Its compounds are found naturally in the milk of various mammals and as a minor constituent of coconut oil and palm kernel oil.[3]

Caprylic acid
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Octanoic acid
Other names
1-Heptanecarboxylic acid
Octylic acid
Octoic acid
C8:0 (Lipid numbers)
Identifiers
CAS Number
  • 124-07-2 check
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28837 check
ChEMBL
  • ChEMBL324846 check
ChemSpider
  • 370 check
DrugBank
  • DB04519 check
ECHA InfoCard100.004.253 Edit this at Wikidata
EC Number
  • 204-677-5
IUPHAR/BPS
  • 4585
KEGG
  • D05220 check
PubChem CID
  • 379
UNII
  • OBL58JN025 check
CompTox Dashboard (EPA)
  • DTXSID3021645 Edit this at Wikidata
InChI
  • InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) check
    Key: WWZKQHOCKIZLMA-UHFFFAOYSA-N check
  • InChI=1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
    Key: WWZKQHOCKIZLMA-UHFFFAOYAH
SMILES
  • CCCCCCCC(=O)O
Properties
Chemical formula
C8H16O2
Molar mass144.214 g·mol−1
AppearanceOily colorless liquid
OdorFaint, fruity-acid; irritating
Density0.910 g/cm3[1]
Melting point16.7 °C (62.1 °F; 289.8 K)[3]
Boiling point239.7 °C (463.5 °F; 512.8 K)[1]
Solubility in water
0.068 g/100 mL[1]
Solubilitysoluble in alcohol, chloroform, ether, CS2, petroleum ether, acetonitrile
log P3.05
Vapor pressure0.25 Pa
Acidity (pKa)4.89[2]

1.055 (2.06–2.63 K)
1.53 (−191 °C)

Magnetic susceptibility (χ)
-101.60·10−6 cm3/mol
Refractive index (nD)
1.4285
Thermochemistry
Heat capacity (C)
297.9 J/K mol
Std enthalpy of
formation (ΔfH⦵298)
-636 kJ/mol
Hazards
NFPA 704 (fire diamond)
3
0
1
COR
Flash point130 °C (266 °F; 403 K)
Autoignition
temperature
440 °C (824 °F; 713 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
10.08 g/kg (orally in rats)[1]
Related compounds
Related compounds
Heptanoic acid, Nonanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
check verify (what is check☒ ?)
Infobox references

Two other acids are named after goats via the Latin word capra: caproic acid (C6) and capric acid (C10). Together, these three fatty acids comprise 15% of the fatty acids in goat milk fat.

UsesEdit

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 algicide, bactericide, fungicide, and herbicide in nurseries, greenhouses, garden centers, and interiors, and on ornamentation. Products containing caprylic acid are formulated as soluble concentrate/liquids and ready-to-use liquids.[5]

Caprylic acid plays an important role in the body's regulation of energy input and output, a function which is performed by the hormone ghrelin. The sensation of hunger is a signal that the body requires an input of energy in the form of food consumption. Ghrelin stimulates hunger by triggering receptors in the hypothalamus. In order to activate these receptors, ghrelin must undergo a process called acylation in which it acquires an -OH group, and caprylic acid provides this by linking at a specific site on ghrelin molecules. Other fatty acids in the same position have similar effects on hunger.[citation needed]

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

Dietary usesEdit

See also: Medium-chain triglyceride § Dietary relevance

Caprylic acid is taken as a dietary supplement. In the body, caprylic acid would be found as octanoate, or unprotonated caprylic acid.[6]

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][11] however, a systematic review of the evidence concluded that the overall results are inconclusive.[12] Also, interest in MCTs has been shown by endurance athletes and the bodybuilding community, but MCTs have not been found to be beneficial to improved exercise performance.[11]

Medical usesEdit

Caprylic acid has been studied as part of a ketogenic diet to treat children with intractable epilepsy.[13] Caprylic acid is currently being researched as a treatment for essential tremor. 


This article uses material from the Wikipedia article
 Metasyntactic variable, which is released under the 
Creative Commons
Attribution-ShareAlike 3.0 Unported License.