Pentadecylic acid

Pentadecylic acid, also known as pentadecanoic acid or C15:0 is an odd-chain saturated fatty acid found primarily in dairy fat, as well as in ruminant meat and some types of fish and plants.[2] 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.[3] The butterfat in cows milk is its major dietary source[4] and it is used as a marker for butterfat consumption. Pentadecylic acid also occurs in hydrogenated mutton fat.[5] It also comprises 3.61% of the fats from the fruit of the durian species Durio graveolens.[6] Pentadecylic acid may decrease mother-to-child transmission of HIV through breastfeeding.[7] Higher circulating concentrations of C15:0 have been associated with a lower risk of developing type 2 diabetes and cardiovascular disease.[8][9][10] 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.[11] C15:0 has been shown to repair mitochondrial function and activate peroxisome proliferator-activated receptors alpha and delta.[11][2] 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.[2] 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.[2]

Pentadecylic acid
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
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).
Infobox references

See also

References
  1. Pentadecanoic acid, Sigma-Aldrich
  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. 119: 514–529. doi:10.1016/j.tifs.2021.12.019. ISSN 0924-2244. S2CID 245406266.
  3. Jost R (2007). "Milk and Dairy Products". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a16_589.pub3.
  4. 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.
  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. Nasaruddin MH, Noor NQ, Mamat H (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.
  7. Villamor E, Koulinska IN, Furtado J, Baylin A, Aboud S, Manji K, et al. (September 2007). "Long-chain n-6 polyunsaturated fatty acids in breast milk decrease the risk of HIV transmission through breastfeeding". The American Journal of Clinical Nutrition. 86 (3): 682–689. doi:10.1093/ajcn/86.3.682. PMID 17823433.
  8. 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.
  9. 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.
  10. 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.
  11. 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.
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