Pentadecylic acid
Names | |
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Preferred IUPAC name Pentadecanoic acid | |
Other names n-Pentadecanoic acid; C15:0 (Lipid numbers) | |
Identifiers | |
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ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.012.448 |
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InChI
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Properties | |
Chemical formula | 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 |
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.
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
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
- ^ 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.
External links
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- Propionic (C3)
- Butyric (C4)
- Valeric (C5)
- Caproic (C6)
- Enanthic (C7)
- Caprylic (C8)
- Pelargonic (C9)
- Capric (C10)
- Undecylic (C11)
- Lauric (C12)
- Tridecylic (C13)
- Myristic (C14)
- Pentadecylic (C15)
- Palmitic (C16)
- Margaric (C17)
- Stearic (C18)
- Nonadecylic (C19)
- Arachidic (C20)
- Heneicosylic (C21)
- Behenic (C22)
- Tricosylic (C23)
- Lignoceric (C24)
- Pentacosylic (C25)
- Cerotic (C26)
- Carboceric (C27)
- Montanic (C28)
- Nonacosylic (C29)
- Melissic (C30)
- Hentriacontylic (C31)
- Lacceroic (C32)
- Psyllic (C33)
- Geddic (C34)
- Ceroplastic (C35)
- Hexatriacontylic (C36)
- Heptatriacontanoic (C37)
- Octatriacontanoic (C38)
- Nonatriacontanoic (C39)
- Tetracontanoic (C40)
- Octenoic (8:1)
- Decenoic (10:1)
- Decadienoic (10:2)
- Lauroleic (12:1)
- Laurolinoleic (12:2)
- Myristovaccenic (14:1)
- Myristolinoleic (14:2)
- Myristolinolenic (14:3)
- Palmitolinolenic (16:3)
- Palmitidonic (16:4)
- α-Linolenic (18:3)
- Stearidonic (18:4)
- α-Parinaric (18:4)
- Dihomo-α-linolenic (20:3)
- Eicosatetraenoic (20:4)
- Eicosapentaenoic (20:5)
- Clupanodonic (22:5)
- Docosahexaenoic (22:6)
- 9,12,15,18,21-Tetracosapentaenoic (24:5)
- 6,9,12,15,18,21-Tetracosahexaenoic (24:6)
- Myristoleic (14:1)
- Palmitovaccenic (16:1)
- α-Eleostearic (18:3)
- β-Eleostearic (trans-18:3)
- Punicic (18:3)
- 7,10,13-Octadecatrienoic (18:3)
- 9,12,15-Eicosatrienoic (20:3)
- β-Eicosatetraenoic (20:4)
- 8-Tetradecenoic (14:1)
- 12-Octadecenoic (18:1)
- Linoleic (18:2)
- Linolelaidic (trans-18:2)
- γ-Linolenic (18:3)
- Calendic (18:3)
- Pinolenic (18:3)
- Dihomo-linoleic (20:2)
- Dihomo-γ-linolenic (20:3)
- Sciadonic (20:3)
- Arachidonic (20:4)
- Adrenic (22:4)
- Osbond (22:5)
- Palmitoleic (16:1)
- Vaccenic (18:1)
- Rumenic (18:2)
- Paullinic (20:1)
- 7,10,13-Eicosatrienoic (20:3)
- Sapienic (16:1)
- Gadoleic (20:1)
- 4-Hexadecenoic (16:1)
- Petroselinic (18:1)
- 8-Eicosenoic (20:1)