Chemistry:Cetoleic acid
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| Names | |
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| IUPAC name
(Z)-docos-11-enoic acid
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C22H42O2 | |
| Molar mass | 338.576 g·mol−1 |
| Density | 0.891 g/cm3 |
| Melting point | 32–33 °C (90–91 °F; 305–306 K) |
| Boiling point | 453.3 °C (847.9 °F; 726.5 K)[1] |
| Hazards | |
| Flash point | 349.9 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Cetoleic acid is a linear very long-chain fatty acid with 22 carbon atoms and one double bond, in the position 11=12 with cis-configuration.[2] The acid belongs to the Omega-11 group.[3][4]
Cetoleic acid is a positional isomer of erucic acid. There is also an isomer with a Δ11 double bond in the trans-configuration, also present in nature, called cetoelaidic acid.
Natural occurrence
The acid is present in the wax esters of jojoba oil at 15–20% and in avellana oil from the Chilean hazelnut (Gevuina avellana) at about 9–10%.[5] It is also present in the glycerol esters of some fish oils, with the concentration in cod liver oil reaching up to 12%. Cetoleic acid is toxic; its toxic effects are similar to those of erucic acid.[6]
Uses
Cetoleic acid may be used in cardiovascular disease research.[7]
Biologcal activity
Cetoleic acid can promote the synthesis of ALA in human HepG2 cells and EPA in vitro in salmon liver cells, affecting cholesterol levels in rodents[8][9].
References
- ↑ "Cetoleic acid Safety Data Sheets". echemi.com. https://www.echemi.com/sds/e-docos-11-enoicacid-pid_Seven5255.html.
- ↑ McClance, R.; Food, Great Britain Ministry of Agriculture, Fisheries and (1998) (in en). Fatty Acids: Seventh Supplement to the Fifth Edition of McCance and Widdowson's The Composition of Foods. Royal Society of Chemistry. p. 174. ISBN 978-0-85404-819-9. https://books.google.com/books?id=b1_NUfXS-JIC&dq=Cetoleic+acid&pg=PA174. Retrieved 14 April 2025.
- ↑ Tobin, D.; Midtbø, L. K.; Mildenberger, J.; Svensen, H.; Stoknes, I. (1 February 2024). "The effect of fish oil rich in cetoleic acid on the omega-3 index and skin quality". Prostaglandins, Leukotrienes and Essential Fatty Acids 201. doi:10.1016/j.plefa.2024.102616. ISSN 0952-3278. PMID 38788345.
- ↑ Østbye, Tone-Kari Knutsdatter; Berge, Gerd Marit; Nilsson, Astrid; Romarheim, Odd Helge; Bou, Marta; Ruyter, Bente (October 2019). "The long-chain monounsaturated cetoleic acid improves the efficiency of the n-3 fatty acid metabolic pathway in Atlantic salmon and human HepG2 cells" (in en). British Journal of Nutrition 122 (7): 755–768. doi:10.1017/S0007114519001478. ISSN 0007-1145. PMID 31288871. https://www.cambridge.org/core/journals/british-journal-of-nutrition/article/longchain-monounsaturated-cetoleic-acid-improves-the-efficiency-of-the-n3-fatty-acid-metabolic-pathway-in-atlantic-salmon-and-human-hepg2-cells/1DAD2BDFE82B86BB58397A3F0EA2CB22. Retrieved 14 April 2025.
- ↑ Peters, Ralf (2015). Brennstoffzellensysteme in der Luftfahrt. Berlin, Heidelberg: Springer Berlin Heidelberg. p. 26. doi:10.1007/978-3-662-46798-5. ISBN 978-3-662-46797-8. https://link.springer.com/book/10.1007/978-3-662-46798-5. Retrieved 14 April 2025.
- ↑ Vries, John De (8 October 2021) (in en). Food Safety and Toxicity. CRC Press. p. 78. ISBN 978-1-4398-2195-4. https://books.google.com/books?id=ag4z1Pp9cLAC&dq=Cetoleic+acid&pg=PA77. Retrieved 14 April 2025.
- ↑ "Cetoleic acid | Long-chain Monounsaturated Fatty Acids | MedChemExpress". MedchemExpress.com. https://www.medchemexpress.com/Cetoleic_acid.html?srsltid=AfmBOoozrrD__hV59OlPHxcdRa5D0dpaWOp3Wc2TgvLCNuJ4aEHDOZa4.
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