Caproic acid: structure, properties, and food sources

Chemical structure of caproic acid

Caproic acid (6 carbon atoms), from the Latin word caper, meaning goat, was first isolated from butter by Chevreul M.E. in 1816.
It is a saturated fatty acid (no double bond so in shorthand 6:0) member of the sub-group called short chain fatty acids (SCFA), up to 6 carbon atoms.

Properties of caproic acid

Caproic Acid
Fig. 1 – Hexanoic Acid

Molecular weight: 116.15828 g/mol
Molecular formula: C6H12O2
IUPAC name: hexanoic acid
PubChem: 8892

In purified form it is a colorless oily liquid, with melting point at -3 °C (26.6 °F; 270.15 K) and boiling point at 205.8 °C (402.44 °F; 478.95 K) at 760 mmHg.

Other names of caproic acid

  • n-caproic acid
  • capronic acid
  • hexoic acid
  • n-hexanoic acid
  • butylacetic acid
  • pentiformic acid
  • n-hexylic acid
  • n-hexoic acid
  • 6:0

Food sources of caproic acid

It occurs as glycerol ester in animal fats like those present in butter, cheddar and other cheeses and in coconut oil.
The unpleasant odor reminiscent of goats is due to its free hence also his name.

References

Akoh C.C. and Min D.B. “Food lipids: chemistry, nutrition, and biotechnology” 3th ed. 2008

Chow Ching K. “Fatty acids in foods and their health implication” 3th ed. 2008

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