Pentadecylic acid
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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).
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Pentadecylic acid, also known as pentadecanoic acid or C15:0 is an odd-chain saturated fatty acid. It is a colorless solid.
A laboratory preparation involves permanganate oxidation of 1-hexadecene (CH3(CH2)13CH=CH2).[2]
Pentadecylic acid is found primarily in dairy fat, as well as in ruminant meat and some types of fish and plants.[3] Its molecular formula is CH3(CH2)13CO2H. It is one of the most common odd-chain fatty acids, although it is rare in nature, comprising 1.2% of milk fat from cows.[4] The butterfat in cows milk is its major dietary source[5] and it is used as a marker for butterfat consumption. Pentadecylic acid also occurs in hydrogenated mutton fat.[6] Higher circulating concentrations of C15:0 have been associated with a lower risk of developing type 2 diabetes and cardiovascular disease.[7][8][9] Higher C15:0 concentrations have also been linked to a lower risk of chronic inflammation, adiposity, metabolic syndrome, nonalcoholic steatohepatitis, chronic obstructive pulmonary disease, Alzheimer's disease, and cancer.[10] C15:0 has been shown to repair mitochondrial function and activate peroxisome proliferator-activated receptors alpha and delta.[10][3] In human cell systems and animal models, C15:0 has also been shown to decrease inflammation, and decrease the severity of anemia, dyslipidemia, and fibrosis.[3] C15:0 has been proposed as an essential fatty acid due to the following: 1) C15:0 is not readily made endogenously, 2) lower C15:0 dietary intake and blood concentrations are associated with higher mortality and a poorer physiological state, and 3) C15:0 has demonstrated activities and efficacy that parallel associated health benefits in humans.[3]
See also
References
- ^ a b Pentadecanoic acid, Sigma-Aldrich
- ^ Donald G. Lee, Shannon E. Lamb, Victor S. Chang (1981). "Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid". Organic Syntheses. 60: 11. doi:10.15227/orgsyn.060.0011.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ a b c d 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.
- ^ Jost R (2007). "Milk and Dairy Products". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_589.pub3.
- ^ 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.
- ^ 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.
- ^ Imamura F, Fretts A, Marklund M, Ardisson Korat AV, Yang WS, Lankinen M, et al. (October 2018). "Fatty acid biomarkers of dairy fat consumption and incidence of type 2 diabetes: A pooled analysis of prospective cohort studies". PLOS Medicine. 15 (10): e1002670. doi:10.1371/journal.pmed.1002670. PMC 6179183. PMID 30303968.
- ^ Huang L, Lin JS, Aris IM, Yang G, Chen WQ, Li LJ (May 2019). "Circulating Saturated Fatty Acids and Incident Type 2 Diabetes: A Systematic Review and Meta-Analysis". Nutrients. 11 (5): 998. doi:10.3390/nu11050998. PMC 6566227. PMID 31052447.
- ^ Trieu K, Bhat S, Dai Z, Leander K, Gigante B, Qian F, et al. (September 2021). "Biomarkers of dairy fat intake, incident cardiovascular disease, and all-cause mortality: A cohort study, systematic review, and meta-analysis". PLOS Medicine. 18 (9): e1003763. doi:10.1371/journal.pmed.1003763. PMC 8454979. PMID 34547017.
- ^ a b Abdoul-Aziz SK, Zhang Y, Wang J (November 2021). "Milk Odd and Branched Chain Fatty Acids in Dairy Cows: A Review on Dietary Factors and Its Consequences on Human Health". Animals. 11 (11): 3210. doi:10.3390/ani11113210. PMC 8614267. PMID 34827941.