Hexanoic acid

Hexanoic acid, also known as caproic acid, is the carboxylic acid derived from hexane with the chemical formula CH
3(CH
2)
4COOH. 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 gives 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 manufacture of its esters for artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols.[1] Salts and esters of hexanoic acid are known as hexanoates or caproates.

Hexanoic acid

Names
IUPAC name Hexanoic acid
Other names Caproic acid; n-Caproic acid; C6:0 (Lipid numbers)
Identifiers
CAS Number	142-62-1 Y
3D model (JSmol)	Interactive image
Beilstein Reference	773837
ChEBI	CHEBI:30776 Y
ChEMBL	ChEMBL14184 Y
ChemSpider	8552 Y
ECHA InfoCard	100.005.046
EC Number	205-550-7
Gmelin Reference	185066
KEGG	C01585 Y
PubChem CID	8892
UNII	1F8SN134MX Y
CompTox Dashboard (EPA)	DTXSID7021607
InChI InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) Y Key: FUZZWVXGSFPDMH-UHFFFAOYSA-N Y InChI=1/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8) Key: FUZZWVXGSFPDMH-UHFFFAOYAY
SMILES CCCCCC(=O)O
Properties
Chemical formula	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]
Solubility in water	1.082 g/100 mL[1]
Solubility	soluble in ethanol, ether
Acidity (pKa)	4.88
Magnetic susceptibility (χ)	-78.55·10−6 cm3/mol
Refractive index (nD)	1.4170
Viscosity	3.1 mP
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H311, H314, H318
GHS precautionary statements	P260, P264, P280, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P322, P361, P363, P405, P501
NFPA 704 (fire diamond)	1 3 0
Flash point	103 °C (217 °F; 376 K)[2]
Autoignition temperature	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)
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).
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Infobox references

Two other acids are named after goats: caprylic (C8) and capric (C10). Along with hexanoic 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.