Pentadecylic acid

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Pentadecylic acid
Pentadecanoic acid.svg
Pentadecylic-acid-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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).

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.

Contents

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] [6] The butterfat in cow milk is its major dietary source, comprising 1.2% of cow milk fat. [3] [7]

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, [8] involving alpha oxidation. [9]

Research

Pentadecanoic acid has been compared to eicosapentaenoic acid (EPA) to evaluate the possibility that pentadecanoic acid is a previously unrecognized essential fatty acid. [10]

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. ↑ 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. doi: 10.9755/ejfa.v26i7.18187 .
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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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