Chemistry:Pentadecylic acid
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 Pentadecanoic acid powder in weighboat
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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 | |
PubChem CID
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| UNII | |
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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). | |
| Infobox references | |
Pentadecylic acid, also known as pentadecanoic acid or C15:0, is an odd-chain saturated fatty acid. Its molecular formula is CH
3(CH
2)
13CO
2H. It is a colorless solid.
A laboratory preparation involves permanganate oxidation of 1-hexadecene (CH
3(CH
2)
13CH=CH
2).[2]
It is one of the most common odd-chain fatty acids, which are 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
- ↑ 1.0 1.1 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.
- ↑ 3.0 3.1 "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2007. doi:10.1002/14356007.a16_589.pub3.
- ↑ "Update on food sources and biological activity of odd-chain, branched and cyclic fatty acids –– A review" (in en). Trends in Food Science & Technology 119: 514–529. 2022-01-01. doi:10.1016/j.tifs.2021.12.019. ISSN 0924-2244.
- ↑ "The occurrence of n-pentadecanoic acid in hydrogenated mutton fat". The Biochemical Journal 58 (4): 516–517. December 1954. doi:10.1042/bj0580516. 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.
- ↑ "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. doi:10.1093/ajcn/69.1.22. PMID 9925119.
- ↑ "Pentadecanoic and Heptadecanoic Acids: Multifaceted Odd-Chain Fatty Acids". Advances in Nutrition 7 (4): 730–4. 2016. doi:10.3945/an.115.011387. PMID 27422507.
- ↑ "Role of 2-hydroxy acyl-CoA lyase HACL2 in odd-chain fatty acid production via α-oxidation in vivo". Mol Biol Cell 34 (9). 2023. doi:10.1091/mbc.E23-02-0042. PMID 37285239.
- ↑ "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). 2022. doi:10.1371/journal.pone.0268778. PMID 35617322. Bibcode: 2022PLoSO..1768778V.
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