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

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.

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

It is one of the most common odd-chain fatty acids, although it is rare in nature.[3] Pentadecylic acid is found primarily in dairy fat, as well as in ruminant meat and some fish and plants.[4][5] The butterfat in cow milk is its major dietary source, comprising 1.2% of cow milk fat.[6][3]

Rare genetic disorders causing unusually high concentrations of C15:0 and C17:0, including Refsum disease, Zellweger Syndrome, and propionic acidemia, confirmed endogenous synthesis of these odd-chain FAs in humans,[7] involving alpha-oxidation.[8]

See also

References

  1. 1 2 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. 1 2 Jost R (2007). "Milk and Dairy Products". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_589.pub3. ISBN 978-3527306732.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ Pfeuffer M, Jaudszus A. "Pentadecanoic and Heptadecanoic Acids: Multifaceted Odd-Chain Fatty Acids". Advances in Nutrition. 7 (4): 730–4. doi:10.3945/an.115.011387. PMC 4942867.
  8. ↑ Mori K, Naganuma T, Kihara A. "Role of 2-hydroxy acyl-CoA lyase HACL2 in odd-chain fatty acid production via α-oxidation in vivo". Mol Biol Cell. 34 (9): ar85. doi:10.1091/mbc.E23-02-0042. PMC 10398889.
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