Pentadecylic acid

Pentadecylic acid
Names
	Preferred IUPAC name Pentadecanoic acid
	Other names n-Pentadecanoic acid; ; C15:0 (Lipid numbers)
Identifiers
CAS Number	1002-84-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:42504;
ChemSpider	13249;
ECHA InfoCard	100.012.448
PubChem CID	13849;
UNII	CCW02D961F ;
CompTox Dashboard (EPA)	DTXSID2021652 ;
	InChI 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);
	SMILES O=C(O)CCCCCCCCCCCCCC;
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)
Boiling point	257 °C (495 °F; 530 K) (100 mmHg)
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.

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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]

Pentadecanoic acid has been compared to eicosapentaenoic acid (EPA) to evaluate the possibility that pentadecanoic acid is a previously unrecognized essential fatty acid.^[10]

[1]
Pentadecanoic acid, Sigma-Aldrich
[2]
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]
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.
[4]
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.
[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]
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.
[7]
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.
[8]
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.
[9]
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.
[10]
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.

Safety data

[Sigma-Aldrich-1] [1]
Pentadecanoic acid, Sigma-Aldrich

[2] [2]
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.

[ull-3] [3]
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.

[:0-4] [4]
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.

[5] [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] [6]
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.

[7] [7]
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.

[8] [8]
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.

[9] [9]
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.

[pmid35617322-10] [10]
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.

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Pentadecylic acid

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Research

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Names


Preferred IUPAC name Pentadecanoic acid
Other names n-Pentadecanoic acid; C15:0 (Lipid numbers)
Identifiers
CAS Number	1002-84-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:42504
ChemSpider	13249
ECHA InfoCard	100.012.448
PubChem CID	13849
UNII	CCW02D961F^Y
CompTox Dashboard (EPA)	DTXSID2021652
InChI 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)
SMILES O=C(O)CCCCCCCCCCCCCC
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