Pentadecylic acid

Pentadecylic acid, also known as pentadecanoic acid or C15:0 is an odd-chain saturated fatty acid. Its molecular formula is CH3(CH2)13CO2H. It is a colorless solid.

Pentadecylic acid
Names
Preferred IUPAC name
Pentadecanoic acid
Other names
n-Pentadecanoic acid;
C15:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.012.448
UNII
  • InChI=1S/C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17/h2-14H2,1H3,(H,16,17)
  • O=C(O)CCCCCCCCCCCCCC
Properties
C15H30O2
Molar mass 242.403 g·mol−1
Density 0.842 g/cm3
Melting point 51 to 53 °C (124 to 127 °F; 324 to 326 K)[1]
Boiling point 257 °C (495 °F; 530 K) (100 mmHg)[1]
Related compounds
Related compounds
 Tetradecanoic acid, Hexadecanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

A laboratory preparation involves permanganate oxidation of 1-hexadecene (CH3(CH2)13CH=CH2).[2]

Pentadecylic acid is found primarily in dairy fat, as well as in ruminant meat and some types of fish and plants.[3] 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.[4]

Because the butterfat in cow milk is its major dietary source,[5] it may be used as a biomarker for butterfat consumption.[6] Pentadecylic acid also occurs in hydrogenated mutton fat.[7]

In reviews of preliminary dietary research, higher circulating concentrations of pentadecyclic acid were associated with a lower risk of developing type 2 diabetes and cardiovascular disease.[6][8]

See also

References
  1. Pentadecanoic acid, Sigma-Aldrich
  2. Lee, Donald G.; Lamb, Shannon E.; Chang, Victor S. (1981). "Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid". Organic Syntheses. 60: 11. doi:10.15227/orgsyn.060.0011.
  3. Dąbrowski G, Konopka I (2022-01-01). "Update on food sources and biological activity of odd-chain, branched and cyclic fatty acids –– A review". Trends in Food Science & Technology. 119: 514–529. doi:10.1016/j.tifs.2021.12.019. ISSN 0924-2244. S2CID 245406266.
  4. Jost R (2007). "Milk and Dairy Products". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_589.pub3.
  5. Smedman AE, Gustafsson IB, Berglund LG, Vessby BO (January 1999). "Pentadecanoic acid in serum as a marker for intake of milk fat: relations between intake of milk fat and metabolic risk factors". The American Journal of Clinical Nutrition. 69 (1): 22–29. doi:10.1093/ajcn/69.1.22. PMID 9925119.
  6. Imamura F, Fretts A, Marklund M, Ardisson Korat AV, Yang WS, Lankinen M, et al. (October 2018). "Fatty acid biomarkers of dairy fat consumption and incidence of type 2 diabetes: A pooled analysis of prospective cohort studies". PLOS Medicine. 15 (10): e1002670. doi:10.1371/journal.pmed.1002670. PMC 6179183. PMID 30303968.
  7. Hansen RP, Shorland FB, Cooke NJ (December 1954). "The occurrence of n-pentadecanoic acid in hydrogenated mutton fat". The Biochemical Journal. 58 (4): 516–517. doi:10.1042/bj0580516. PMC 1269934. PMID 13229996.
  8. Trieu K, Bhat S, Dai Z, Leander K, Gigante B, Qian F, et al. (September 2021). "Biomarkers of dairy fat intake, incident cardiovascular disease, and all-cause mortality: A cohort study, systematic review, and meta-analysis". PLOS Medicine. 18 (9): e1003763. doi:10.1371/journal.pmed.1003763. PMC 8454979. PMID 34547017.
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