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Hexanoic acid

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Title: Hexanoic acid  
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Subject: Fatty acids, Elaidic acid, Lignoceric acid, Stearidonic acid, Arachidic acid
Collection: Alkanoic Acids, Carboxylic Acids, Fatty Acids
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Hexanoic acid

Hexanoic acid
Skeletal formula
Ball-and-stick model
Names
IUPAC name
Hexanoic acid
Other names
Caproic acid; n-Caproic acid; C6:0 (Lipid numbers)
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
KEGG  Y
PubChem
UNII  Y
Properties
C6H12O2
Molar mass 116.16 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; 479.0 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
1
3
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):
LD50 (Median dose)
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).
 Y  (: Y/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  
  2. ^ a b Record in the GESTIS Substance Database of the IFA
  3. ^ Ginkgo.html
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