Hexanoic acid

Caproic acid, also known as hexanoic acid or C6:0, is a medium-chain fatty acid. Medium-chain fatty acids (MCFA) are fatty acids with aliphatic tails of 6 to 12 carbons, which can form medium-chain triglycerides. Caproic acid is a colourless oily liquid that smells like cheese with an overlying waxy or barnyard odor like that of goats or other barnyard animals. Its name comes from the Latin word capra, meaning "goat". Two other fatty 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 acid is a fatty acid found naturally in various animal fats and oils. While generally more abundant in animals, caproic acid is found in all organisms ranging from bacteria to plants to animals. Caproic acid is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo fruit its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. Industrially, 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. Caproic acid has been associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism. As a relatively volatile organic compound, caproic acid has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230).

ID EC Number Name
KEGG:R03620 3.5.1.39 N-methylhexanamide amidohydrolase
Rhea:RHEA:20082 3.5.1.39 N-methylhexanamide + H2O => hexanoate + methylamine
Rhea:RHEA:20083 3.5.1.39 hexanoate + methylamine => N-methylhexanamide + H2O
Rhea:RHEA:20084 3.5.1.39 N-methylhexanamide + H2O <=> hexanoate + methylamine
Rhea:RHEA:38888 N-hexanoyl-sphinganine + H2O => hexanoate + sphinganine
Rhea:RHEA:38889 hexanoate + sphinganine => N-hexanoyl-sphinganine + H2O
Rhea:RHEA:38890 N-hexanoyl-sphinganine + H2O <=> hexanoate + sphinganine
Rhea:RHEA:40116 hexanoyl-CoA + H2O => hexanoate + CoA + H+
Rhea:RHEA:40117 hexanoate + CoA + H+ => hexanoyl-CoA + H2O
Rhea:RHEA:40118 hexanoyl-CoA + H2O <=> hexanoate + CoA + H+
Rhea:RHEA:40612 trihexanoylglycerol + H2O => 2,3-dihexanoyl-sn-glycerol + hexanoate + H+
Rhea:RHEA:40613 2,3-dihexanoyl-sn-glycerol + hexanoate + H+ => trihexanoylglycerol + H2O
Rhea:RHEA:40614 trihexanoylglycerol + H2O <=> 2,3-dihexanoyl-sn-glycerol + hexanoate + H+
Rhea:RHEA:41296 N-(hexanoyl)sphing-4-enine + H2O => hexanoate + sphing-4-enine
Rhea:RHEA:41297 hexanoate + sphing-4-enine => N-(hexanoyl)sphing-4-enine + H2O
Rhea:RHEA:41298 N-(hexanoyl)sphing-4-enine + H2O <=> hexanoate + sphing-4-enine
Rhea:RHEA:43741 hexanoate + ATP + CoA => hexanoyl-CoA + AMP + diphosphate
Rhea:RHEA:43742 hexanoyl-CoA + AMP + diphosphate => hexanoate + ATP + CoA
Rhea:RHEA:43743 hexanoate + ATP + CoA <=> hexanoyl-CoA + AMP + diphosphate
Rhea:RHEA:47353 a hexanoate ester + H2O => an aliphatic alcohol + hexanoate + H+
Rhea:RHEA:47354 an aliphatic alcohol + hexanoate + H+ => a hexanoate ester + H2O
Rhea:RHEA:47355 a hexanoate ester + H2O <=> an aliphatic alcohol + hexanoate + H+
Rhea:RHEA:53497 1-hexanoyl-2-acyl-sn-glycero-3-phosphocholine + H2O => hexanoate + a 2-acyl-sn-glycero-3-phosphocholine + H+
Rhea:RHEA:53498 hexanoate + a 2-acyl-sn-glycero-3-phosphocholine + H+ => 1-hexanoyl-2-acyl-sn-glycero-3-phosphocholine + H2O
Rhea:RHEA:53499 1-hexanoyl-2-acyl-sn-glycero-3-phosphocholine + H2O <=> hexanoate + a 2-acyl-sn-glycero-3-phosphocholine + H+
Rhea:RHEA:54465 1-octadecanoyl-2-hexanoyl-sn-glycero-3-phosphocholine + H2O => hexanoate + 1-octadecanoyl-sn-glycero-3-phosphocholine + H+
Rhea:RHEA:54466 hexanoate + 1-octadecanoyl-sn-glycero-3-phosphocholine + H+ => 1-octadecanoyl-2-hexanoyl-sn-glycero-3-phosphocholine + H2O
Rhea:RHEA:54467 1-octadecanoyl-2-hexanoyl-sn-glycero-3-phosphocholine + H2O <=> hexanoate + 1-octadecanoyl-sn-glycero-3-phosphocholine + H+
Rhea:RHEA:58965 hexanal + O2 + H2O => hexanoate + H2O2 + H+
Rhea:RHEA:58966 hexanoate + H2O2 + H+ => hexanal + O2 + H2O