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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| Names | |
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| Preferred IUPAC name
Pentadecanoic acid | |
| Other names
n-Pentadecanoic acid;
C15:0 (Lipid numbers) | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.012.448 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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
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Tetradecanoic acid, Hexadecanoic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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][6] The butterfat in cow milk is its major dietary source, comprising 1.2% of cow milk fat.[7][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,[8] involving alpha-oxidation.[9]
Research
editPentadecanoic 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
editReferences
edit- ^ a b Pentadecanoic acid, Sigma-Aldrich
- ^ 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.
- ^ a b 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.