Caproic Acid - Wikipedia
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| Names | |
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| IUPAC name Hexanoic acid | |
| Preferred IUPAC name Hexanoic acid | |
| Other names Hexoic acidHexylic acidButylacetic acidPentylformic acid1-Pentanecarboxylic acidC6:0 (Lipid numbers) | |
| Identifiers | |
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| 3D model (JSmol) |
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| Beilstein Reference | 773837 |
| ChEBI |
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| ChEMBL |
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| ECHA InfoCard | 100.005.046  |
| EC Number |
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| Gmelin Reference | 185066 |
| KEGG |
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| CompTox Dashboard (EPA) |
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InChI
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| Properties | |
| Chemical formula | 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] |
| Solubility in water | 1.082 g/100 mL[1] |
| Solubility | soluble in ethanol, ether |
| Acidity (pKa) | 4.88 |
| Magnetic susceptibility (χ) | −78.55·10−6 cm3/mol |
| Refractive index (nD) | 1.4170 |
| Viscosity | 3.1 mP |
| Hazards | |
| GHS labelling: | |
| Pictograms |  |
| Signal word | Danger |
| Hazard statements | H314 |
| Precautionary statements | 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] |
| Autoignitiontemperature | 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 their standard state (at 25 °C [77 °F], 100 kPa).  verify (what is  ?) Infobox references | |
Caproic acid, also known as hexanoic acid, is the carboxylic acid derived from hexane with the chemical formula CH3(CH2)4COOH. It is a colorless oily liquid with a fatty, cheesy, waxy odor resembling that of goats[1] or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor.[3] It is also one of the components of vanilla and cheese. Salts and esters of caproic acid are known as caproates or hexanoates.
Two other acids are named after goats: caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15% of the fat in goat'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.
Properties
[edit]Caproic acid is a 6-Carbon saturated 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 synthesize Medium-chain triglycerides.
Uses
[edit]The primary use of caproic acid is in the manufacture of its esters for use as artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols.[1] Several progestin medications are caproate esters, such as hydroxyprogesterone caproate and gestonorone 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 the 5-alpha-reductase enzyme.[8][9]
See also
[edit]- List of carboxylic acids
- List of saturated fatty acids
- Caproate fermentation
References
[edit]- ^ a b c d e f The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.). Merck. 1989. ISBN 091191028X.
- ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ "Ginkgo.html". Archived from the original on 2008-12-26. Retrieved 2007-03-08.
- ^ "What is Caproic Acid? Cosmetic usage, alternatives, and regulatory insights". Slate. Retrieved 2026-01-07.
- ^ PubChem. "Hexanoic Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-07.
- ^ "Hexanoic acid | 142-62-1". amp.chemicalbook.com. Retrieved 2026-01-07.
- ^ "Industrial Applications of Hexanoic Acid (CAS 142-62-1)". www.nbinno.com. Retrieved 2026-01-07.
- ^ Salvador, Jorge A.R.; Pinto, Rui M.A.; Silvestre, Samuel M. . (2013). Steroidal 5α-reductase and 17α-hydroxylase/17,20-lyase (CYP17) inhibitors useful in the treatment of prostatic diseases. The Journal of Steroid Biochemistry and Molecular Biology, 137(), 199–222. doi:10.1016/j.jsbmb.2013.04.006
- ^ Yazmín Arellano; Eugene Bratoeff; Mariana Garrido; Juan Soriano; Yvonne Heuze; Marisa Cabeza. (2011). New ester derivatives of dehydroepiandrosterone as 5α-reductase inhibitors. , 76(12), 0–1246. doi:10.1016/j.steroids.2011.05.015
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| Saturated |
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| ω−3 Unsaturated |
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| ω−5 Unsaturated |
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| ω−6 Unsaturated |
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| ω−7 Unsaturated |
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| ω−9 Unsaturated |
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| ω−10 Unsaturated |
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| ω−11 Unsaturated |
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| ω−12 Unsaturated |
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| Authority control databases |
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