Pentadecylic acid

{{Chembox | ImageFile = pentadecanoic acid.svg | ImageClass = skin-invert | ImageSize = 250px | ImageFile1 = Pentadecylic-acid-3D-balls.png | ImageClass1 = bg-transparent | ImageSize1 = 250px | ImageCaption2 = Pentadecanoic acid powder in weighboat | ImageFile2 = Pentadecylic or pentadecanoic acid powder in weighboat.jpg | ImageClass2 = skin-invert | ImageSize2 = 250px | PIN = Pentadecanoic acid | OtherNames = ''n''-Pentadecanoic acid;<br />C15:0 (Lipid numbers) |Section1={{Chembox Identifiers | CASNo = 1002-84-2 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = CCW02D961F | PubChem = 13849 | ChemSpiderID = 13249 | ChEBI = 42504 | SMILES = O=C(O)CCCCCCCCCCCCCC | 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) }} |Section2={{Chembox Properties | C=15 | H=30 | O=2 | Appearance = | Density = 0.842 g/cm<sup>3</sup> | MeltingPtC = 51 to 53 | MeltingPt_ref =<ref name=Sigma-Aldrich>[http://www.sigmaaldrich.com/catalog/product/fluka/91446?lang=en&region=US Pentadecanoic acid], Sigma-Aldrich</ref> | BoilingPtC = 257 | BoilingPt_notes = (100 mmHg)<ref name=Sigma-Aldrich/> | Solubility = }} |Section3={{Chembox Hazards | GHSPictograms = {{GHS07}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|315|319|335}} | PPhrases = {{P-phrases|261|264|264+265|271|280|302+352|304+340|305+351+338|319|321|332+317|337+317|362+364|403+233|405|501}} | MainHazards = | FlashPt = | AutoignitionPt = }} |Section8={{Chembox Related | OtherCompounds = Tetradecanoic acid, Hexadecanoic acid }} }}

'''Pentadecylic acid''', also known as '''pentadecanoic acid''' or C15:0, is an odd-chain saturated fatty acid. Its molecular formula is {{chem2|CH3(CH2)13CO2H}}. It is a colorless solid.

A laboratory preparation involves permanganate oxidation of 1-hexadecene ({{chem2|CH3(CH2)13CH\dCH2}}).<ref>{{cite journal |doi=10.15227/orgsyn.060.0011 |title=Carboxylic Acids from the Oxidation of Terminal Alkenes by Permanganate: Nonadecanoic Acid |journal=Organic Syntheses |year=1981 |volume=60 |page=11 |first1=Donald G. |last1=Lee |first2=Shannon E. |last2=Lamb |first3=Victor S. |last3=Chang}}</ref>

It is one of the most common odd-chain fatty acids, which are rare in nature.<ref name="ull">{{Ullmann|doi=10.1002/14356007.a16_589.pub3|isbn = 978-3527306732|title= Milk and Dairy Products|year = 2007| vauthors = Jost R }}</ref> Pentadecylic acid is found primarily in dairy fat, as well as in ruminant meat and some fish and plants.<ref name=":0">{{Cite journal| vauthors = Dąbrowski G, Konopka I |date=2022-01-01|title=Update on food sources and biological activity of odd-chain, branched and cyclic fatty acids –– A review |journal=Trends in Food Science & Technology|language=en|volume=119|pages=514–529|doi=10.1016/j.tifs.2021.12.019|s2cid=245406266|issn=0924-2244}}</ref><ref>{{cite journal | vauthors = Hansen RP, Shorland FB, Cooke NJ | title = The occurrence of n-pentadecanoic acid in hydrogenated mutton fat | journal = The Biochemical Journal | volume = 58 | issue = 4 | pages = 516–517 | date = December 1954 | pmid = 13229996 | pmc = 1269934 | doi = 10.1042/bj0580516 }}</ref><ref>{{Cite journal |last1=Villa |first1=Diana Yamile Gallego |last2=Russo |first2=Luigi |last3=Kerbab |first3=Khawla |last4=Landi |first4=Maddalena |last5=Rastrelli |first5=Luca |date=2014 |title=Chemical and nutritional characterization of Chenopodium pallidicaule (cañihua) and Chenopodium quinoa (quinoa) seeds |journal=Emirates Journal of Food and Agriculture |volume=26 |issue=7 |pages=609–615|doi=10.9755/ejfa.v26i7.18187 |doi-access=free }} </ref> The butterfat in cow milk is its major dietary source, comprising 1.2% of cow milk fat.<ref name=ull/><ref>{{cite journal | vauthors = Smedman AE, Gustafsson IB, Berglund LG, Vessby BO | title = Pentadecanoic acid in serum as a marker for intake of milk fat: relations between intake of milk fat and metabolic risk factors | journal = The American Journal of Clinical Nutrition | volume = 69 | issue = 1 | pages = 22–29 | date = January 1999 | pmid = 9925119 | doi = 10.1093/ajcn/69.1.22 | doi-access = free}}</ref>

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,<ref>{{cite journal |vauthors = Pfeuffer M, Jaudszus A |title = Pentadecanoic and Heptadecanoic Acids: Multifaceted Odd-Chain Fatty Acids |journal = Advances in Nutrition |date = 2016 |volume = 7 | issue = 4 | pages = 730–4 |doi = 10.3945/an.115.011387|pmid = 27422507 |pmc = 4942867 }}</ref> involving alpha oxidation.<ref>{{cite journal |vauthors=Mori K, Naganuma T, Kihara A |title = Role of 2-hydroxy acyl-CoA lyase HACL2 in odd-chain fatty acid production via α-oxidation in vivo |journal = Mol Biol Cell |date = 2023 |volume = 34 | issue = 9 | article-number = ar85| doi = 10.1091/mbc.E23-02-0042|pmid = 37285239 |pmc = 10398889 }}</ref>

== Research == Pentadecanoic acid has been compared to eicosapentaenoic acid (EPA) to evaluate the possibility that pentadecanoic acid is a previously unrecognized essential fatty acid.<ref name="pmid35617322">{{cite journal | vauthors = Venn-Watson SK, Butterworth CN | title=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 | journal=PLOS One | volume=17 | issue=5 | article-number=e0268778 | year=2022 | doi= 10.1371/journal.pone.0268778 | doi-access=free | pmc=9135213 | pmid=35617322| bibcode=2022PLoSO..1768778V }}</ref>

== References == {{reflist}}

== External links == *[http://msds.chem.ox.ac.uk/PE/pentadecanoic_acid.html Safety data]

Category:Fatty acids Category:Alkanoic acids