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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)
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]
Density 0.93 g/cm3[2]
Melting point −3.4 °C (25.9 °F; 269.8 K)
Boiling point 205 °C (401 °F; 478 K)
1.082 g/100 g[1]
Acidity (pKa) 4.88
Hazards
Flash point 103 °C (217 °F)[2]
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, cheesey, waxy and 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] 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 acid (Capric is a crystal or wax like substance while the other 2 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