Pentadecylic acid, also known as pentadecanoic acid or C15:0 is an odd-chain
saturated fatty acid
A saturated fat is a type of fat in which the fatty acid chains have all single bonds. A fat known as a glyceride is made of two kinds of smaller molecules: a short glycerol backbone and fatty acids that each contain a long linear or branched ch ...
. It is a colorless solid.
A laboratory preparation involves
permanganate
A permanganate () is a chemical compound containing the manganate(VII) ion, , the conjugate base of permanganic acid. Because the manganese atom is in the +7 oxidation state, the permanganate(VII) ion is a strong oxidizing agent. The ion is a tra ...
oxidation of
1-hexadecene
1-Hexadecene, also known as 1-cetene, is a long-chain hydrocarbon and an alkene with the molecular formula CH2=CH(CH2)13CH3. It is one of many isomers of hexadecene. Classified as an alpha-olefin, 1-hexadecene is a colorless liquid.
1-Hexadec ...
(CH
3(CH
2)
13CH=CH
2).
Pentadecylic acid is found primarily in dairy fat, as well as in ruminant meat and some types of fish and plants.
Its molecular formula is CH
3(CH
2)
13CO
2H. It is one of the most common
odd-chain fatty acids, although it is rare in nature, comprising 1.2% of milk fat from cows. The
butterfat in cows
milk
Milk is a white liquid food produced by the mammary glands of mammals. It is the primary source of nutrition for young mammals (including breastfed human infants) before they are able to digestion, digest solid food. Immune factors and immune ...
is its major dietary source
and it is used as a marker for butterfat consumption. Pentadecylic acid also occurs in hydrogenated mutton fat. Higher circulating concentrations of C15:0 have been associated with a lower risk of developing type 2 diabetes and cardiovascular disease.
Higher C15:0 concentrations have also been linked to a lower risk of chronic inflammation, adiposity, metabolic syndrome, nonalcoholic steatohepatitis, chronic obstructive pulmonary disease, Alzheimer's disease, and cancer.
C15:0 has been shown to repair mitochondrial function and activate peroxisome proliferator-activated receptors alpha and delta.
In human cell systems and animal models, C15:0 has also been shown to decrease inflammation, and decrease the severity of anemia, dyslipidemia, and fibrosis.
C15:0 has been proposed as an essential fatty acid due to the following: 1) C15:0 is not readily made endogenously, 2) lower C15:0 dietary intake and blood concentrations are associated with higher mortality and a poorer physiological state, and 3) C15:0 has demonstrated activities and efficacy that parallel associated health benefits in humans.
See also
*
List of saturated fatty acids
*
List of carboxylic acids
*
Margaric acid
Margaric acid, or heptadecanoic acid, is a saturated fatty acid. Its molecular formula is CH3(CH2)15CO2H. Classified as an odd-chain fatty acid, it occurs as a trace component of the fat and milkfat of ruminants. Salts and esters of margaric acid ...
References
External links
Safety data
{{Fatty acids
Fatty acids
Alkanoic acids