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Caproic acid

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Caproic acid
Skeletal formula
Ball-and-stick model
Names
IUPAC name
Hexanoic acid
Other names
Caproic acid; n-Caproic acid; C6:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.046 Edit this at Wikidata
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
1.4170
Viscosity 3.1 mP
Hazards
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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Hexanoic acid (caproic acid) is the carboxylic acid derived from hexane with the general formula C5H11COOH. It is a colorless oily liquid with an odor that is fatty, cheesy, waxy, and like 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 give the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor.[3] It is also one of the components of vanilla. The primary use of hexanoic acid is in the manufacture of its esters for artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols.[1]

The salts and esters of this acid are known as hexanoates or caproates.

Two other acids are named after goats: caprylic (C8) and capric (C10). Along with hexanoic acid, these total 15% in goat milk fat.

Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other two are mobile liquids) are not only used for the formation of esters, but also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.

References

  1. ^ a b c d e f The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X
  2. ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. ^ Ginkgo.html
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