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Caproic acid

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(Redirected from Hexanoic acid)
Caproic acid
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
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 Edit this at Wikidata
EC Number
  • 205-550-7
185066
KEGG
UNII
  • InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) checkY
    Key: FUZZWVXGSFPDMH-UHFFFAOYSA-N checkY
  • InChI=1/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
    Key: FUZZWVXGSFPDMH-UHFFFAOYAY
  • CCCCCC(=O)O
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 in ethanol, ether
Acidity (pKa) 4.88
−78.55·10−6 cm3/mol
1.4170
Viscosity 3.1 mP
Hazards
GHS labelling:
GHS05: Corrosive
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
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):
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).
checkY verify (what is checkYX markN ?)

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]

References

[edit]
  1. 1 2 3 4 5 6 The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.). Merck. 1989. ISBN 091191028X.
  2. 1 2 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ↑ "Ginkgo.html". Archived from the original on 2008-12-26. Retrieved 2007-03-08.
  4. ↑ "What is Caproic Acid? Cosmetic usage, alternatives, and regulatory insights". Slate. Retrieved 2026-01-07.
  5. ↑ PubChem. "Hexanoic Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-07.
  6. ↑ "Hexanoic acid | 142-62-1". amp.chemicalbook.com. Retrieved 2026-01-07.
  7. ↑ "Industrial Applications of Hexanoic Acid (CAS 142-62-1)". www.nbinno.com. Retrieved 2026-01-07.
  8. ↑ 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
  9. ↑ 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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