Caproic acid

Caproic acid
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Hexanoic acid
Other names
Hexoic acid; Hexylic acid; Butylacetic acid; Pentylformic acid; 1-Pentanecarboxylic acid; C6:0 (Lipid numbers)
Identifiers
  • 142-62-1 checkY
3D model (JSmol)
  • Interactive image
773837
ChEBI
  • CHEBI:30776 checkY
ChEMBL
  • ChEMBL14184 checkY
ChemSpider
  • 8552 checkY
ECHA InfoCard100.005.046
EC Number
  • 205-550-7
185066
KEGG
  • C01585 checkY
  • 8892
UNII
  • 1F8SN134MX checkY
  • DTXSID7021607
  • 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 mass116.160 g·mol−1
AppearanceOily liquid[1]
Odorgoat-like
Density0.929 g/cm3[2]
Melting point−3.4 °C (25.9 °F; 269.8 K)[1]
Boiling point205.8 °C (402.4 °F; 478.9 K)[1]
1.082 g/100 mL[1]
Solubilitysoluble in ethanol, ether
Acidity (pKa)4.88
−78.55·10−6 cm3/mol
1.4170
Viscosity3.1 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 point103 °C (217 °F; 376 K)[2]
380 °C (716 °F; 653 K)
Explosive limits1.3-9.3%
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 checkY☒N ?)

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. 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] Salts and esters of caproic acid are known as caproates or hexanoates. Several progestin medications are caproate esters, such as hydroxyprogesterone caproate and gestonorone caproate.

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 not only used for the formation of esters, but also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.

See also

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". Archived from the original on 2008-12-26. Retrieved 2007-03-08.
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