Cetoleic acid

Last updated
Cetoleic acid
Cetoleic acid folded.svg
Names
IUPAC name
(Z)-docos-11-enoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h11-12H,2-10,13-21H2,1H3,(H,23,24)/b12-11-
    Key: KJDZDTDNIULJBE-QXMHVHEDSA-N
  • CCCCCCCCCC/C=C\CCCCCCCCCC(=O)O
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).

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]

Contents

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]

References

  1. ↑ "Cetoleic acid Safety Data Sheets". echemi.com. Retrieved 14 April 2025.
  2. ↑ McClance, R.; Food, Great Britain Ministry of Agriculture, Fisheries and (1998). 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 . Retrieved 14 April 2025.{{cite book}}: CS1 maint: multiple names: authors list (link)
  3. ↑ 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: 102616. doi: 10.1016/j.plefa.2024.102616 . ISSN   0952-3278. PMID   38788345 . Retrieved 14 April 2025.
  4. ↑ 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". British Journal of Nutrition . 122 (7): 755–768. doi:10.1017/S0007114519001478. hdl: 11250/2620970 . ISSN   0007-1145. PMID   31288871 . Retrieved 14 April 2025.
  5. ↑ Peters, Ralf (2015). Peters, Ralf (ed.). 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 . Retrieved 14 April 2025.
  6. ↑ Vries, John De (8 October 2021). Food Safety and Toxicity. CRC Press. p. 78. ISBN   978-1-4398-2195-4 . Retrieved 14 April 2025.
  7. ↑ "Cetoleic acid | Long-chain Monounsaturated Fatty Acids | MedChemExpress". MedchemExpress.com. Retrieved 14 April 2025.
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