Pentadecylic_acid

Pentadecylic acid

Pentadecylic acid

Chemical compound

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.

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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]

Research

Pentadecanoic acid has been compared to eicosapentaenoic acid (EPA) to evaluate the possibility that pentadecanoic acid is a previously unrecognized essential fatty acid.[9]

See also

References

  1. [1]
    Pentadecanoic acid, Sigma-Aldrich
  2. [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. [3]
    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. [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. [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. [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. [7]
    Pfeuffer M, Jaudszus A (2016). "Pentadecanoic and Heptadecanoic Acids: Multifaceted Odd-Chain Fatty Acids". Advances in Nutrition. 7 (4): 730–4. doi:10.3945/an.115.011387. PMC 4942867. PMID 27422507.
  8. [8]
    Mori K, Naganuma T, Kihara A (2023). "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. PMID 37285239.
  9. [9]
    Venn-Watson SK, Butterworth CN (2022). "Broader and safer clinically-relevant activities of pentadecanoic acid compared to omega-3: Evaluation of an emerging essential fatty acid across twelve primary human cell-based disease systems". PLOS One. 17 (5): e0268778. Bibcode:2022PLoSO..1768778V. doi:10.1371/journal.pone.0268778. PMC 9135213. PMID 35617322.
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