Caproleic acid: structure, properties, and food sources

Caproleic acid, a carboxylic acid with a 10 carbon chain10, is an uncommon monounsaturated fatty acid that contains a single cis double bond at position 9 with respect to the carboxyl end, whereas, with respect to the methyl end, it is located at carbon 1. In shorthand it is named 10:1n-1.
It is a member of the sub-group called medium chain fatty acids or MCFA, fatty acids containg from 6 to 12 carbon atoms in their aliphatic chain.

PROPERTIES
Molecular weight: 170.24872 g/mol
Molecular formula: C10H18O2
IUPAC name: dec-9-enoic acid
CAS registry number: 14436-32-9
PubChem: 61743

Skeletal formula of caproleic acid, an unsaturated fatty acid
Caproleic Acid

In purified form it is a colorless clear liquid insoluble in water with boiling point at 269-271 °C (516.2-519.8 °F; 542.15-544.15 K) at 760 mm Hg.

OTHER NAMES
9-decenoic acid
delta(9)-decenoic acid
10:1

Food sources of caproleic acid

It occurs as glycerol ester in animal fats like these present in milk, butter and Parmigiano.
In nature it is produced by mushrooms of the Xerula longipes and Xerula pudens species.

References

  1. Akoh C.C. and Min D.B. “Food lipids: chemistry, nutrition, and biotechnology” 3th ed. 2008
  2. Chow Ching K. “Fatty acids in foods and their health implication” 3th ed. 2008

Biochemistry, metabolism and nutrition