Cetoleic acid
From Wikipedia, the free encyclopedia
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| Names | |
|---|---|
| IUPAC name
(Z)-docos-11-enoic acid | |
| 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).
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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.
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]