Pentadecylic acid explained

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

A laboratory preparation involves permanganate oxidation of 1-hexadecene .[1]

It is one of the most common odd-chain fatty acids, although it is rare in nature. Pentadecylic acid is found primarily in dairy fat, as well as in ruminant meat and some fish and plants.[2] [3] [4] The butterfat in cow milk is its major dietary source, comprising 1.2% of cow milk fat.[5]

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,[6] involving alpha-oxidation.[7]

Research

Pentadecanoic acid has been compared to eicosapentaenoic acid (EPA) to evaluate the possibility that pentadecanoic acid is a previously unrecognized essential fatty acid.[8]

See also

External links

Notes and References

  1. 10.15227/orgsyn.060.0011 . Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid . Organic Syntheses . 1981 . 60 . 11 . Donald G. . Lee . Shannon E. . Lamb . Victor S. . Chang.
  2. 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. en. 119. 514–529. 10.1016/j.tifs.2021.12.019. 245406266. 0924-2244.
  3. Hansen RP, Shorland FB, Cooke NJ . The occurrence of n-pentadecanoic acid in hydrogenated mutton fat . The Biochemical Journal . 58 . 4 . 516–517 . December 1954 . 13229996 . 1269934 . 10.1042/bj0580516 .
  4. Villa . Diana Yamile Gallego . Russo . Luigi . Kerbab . Khawla . Landi . Maddalena . Rastrelli . Luca . 2014 . Chemical and nutritional characterization of Chenopodium pallidicaule (cañihua) and Chenopodium quinoa (quinoa) seeds . Emirates Journal of Food and Agriculture . 26 . 7 . 609–615. 10.9755/ejfa.v26i7.18187 . free .
  5. Smedman AE, Gustafsson IB, Berglund LG, Vessby BO . 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 . January 1999 . 9925119 . 10.1093/ajcn/69.1.22 . free.
  6. Pfeuffer M, Jaudszus A . Pentadecanoic and Heptadecanoic Acids: Multifaceted Odd-Chain Fatty Acids . Advances in Nutrition . 2016 . 7 . 4 . 730–4 . 10.3945/an.115.011387. 27422507 . 4942867 .
  7. 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 . 2023 . 34 . 9 . ar85. 10.1091/mbc.E23-02-0042. 37285239 . 10398889 .
  8. Venn-Watson SK, Butterworth CN . 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 . . 17 . 5 . e0268778 . 2022 . 10.1371/journal.pone.0268778 . free . 9135213 . 35617322. 2022PLoSO..1768778V .

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