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| Names | |
|---|---|
| IUPAC name Hexanoic acid | |
| Preferred IUPAC name Hexanoic acid | |
| Other names Hexoic acid Hexylic acid Butylacetic acid Pentylformic acid 1-Pentanecarboxylic acid C6:0 (Lipid numbers) | |
| Identifiers | |
| |
3D model (JSmol) | |
| 773837 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.005.046 |
| EC Number |
|
| 185066 | |
| KEGG |
|
| UNII | |
| |
| |
| Properties | |
| C6H12O2 | |
| Molar mass | 116.160 g·mol−1 |
| Appearance | Oily liquid[1] |
| Odor | goat-like |
| Density | 0.929 g/cm3[2] |
| Melting point | −3.4 °C (25.9 °F; 269.8 K)[1] |
| Boiling point | 205.8 °C (402.4 °F; 478.9 K)[1] |
| 1.082 g/100 mL[1] | |
| Solubility | soluble inethanol,ether |
| Acidity (pKa) | 4.88 |
| −78.55·10−6 cm3/mol | |
Refractive index (nD) | 1.4170 |
| Viscosity | 3.1 mP |
| Hazards | |
| GHS labelling: | |
 | |
| Danger | |
| H314 | |
| P260,P264,P280,P301+P330+P331,P302+P352,P303+P361+P353,P304+P340,P305+P351+P338,P310,P312,P321,P322,P361,P363,P405,P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 103 °C (217 °F; 376 K)[2] |
| 380 °C (716 °F; 653 K) | |
| Explosive limits | 1.3-9.3% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 3000 mg/kg (rat, oral) |
| Related compounds | |
Related compounds | Pentanoic acid,Heptanoic acid |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Caproic acid, also known ashexanoic acid, is thecarboxylic acid derived fromhexane with the chemical formulaCH3(CH2)4COOH. It is a colorless oily liquid with a fatty, cheesy, waxy odor resembling that ofgoats[1] or other barnyardanimals. It is afatty acid found naturally in various animalfats andoils, and is one of the chemicals that gives the decomposing fleshy seed coat of theginkgo its characteristic unpleasant odor.[3] It is also one of the components ofvanilla andcheese.Salts andesters of caproic acid are known ascaproates orhexanoates.
Two other acids are named after goats:caprylic acid (C8) andcapric acid (C10). Along with caproic acid, they account for 15% of the fat ingoat's milk.
Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other two are mobile liquids) are used for the formation of esters, and also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.
Caproic acid is a 6-Carbonsaturated fatty acid. It occurs in a white crystalline solid form or a colorless to pale yellow liquid state, accompanied by a strong and unpleasant odor. It has limited solubility in water, although it is soluble in dimethyl ether, benzene and other organic solvents.[4][5]
It may be prepared by fractionation of the volatile fatty acids of coconut oil.[6] Caproic acid belongs to the family of medium chain fatty acids (MCFAs) which can be used to synthesizeMedium-chain triglycerides.
The primary use of caproic acid is in the manufacture of itsesters for use as artificial flavors, and in the manufacture of hexylderivatives, such ashexylphenols.[1] Severalprogestin medications are caproate esters, such ashydroxyprogesterone caproate andgestonorone caproate. Its derivatives are also used in soaps, shampoos, conditioners and gels.
Caproic acid is also used as a component in varnish driers, as well as a lubricant. Its derivatives can also be incorporated to modify the elasticity, strength, and resilience of rubber products.[7]
DHEA-caproate ester (#121) has a IC50 of 0.049nM for the5-alpha-reductase enzyme.[8][9]
