Eicosadienoic acid

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Eicosadienoic acid
Eicosadienoic acid.svg
Names
IUPAC name
(11Z,14Z)-icosa-11,14-dienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9-
    Key: XSXIVVZCUAHUJO-HZJYTTRNSA-N
  • CCCCCC=CCC=CCCCCCCCCCC(=O)O
Properties
C20H36O2
Molar mass 308.506 g·mol−1
Appearancecolorless liquid [1]
Density 0.9 g/cm³
Melting point 148.9 °C (300.0 °F; 422.0 K)
Boiling point 198 °C (388 °F; 471 K) [2]
insoluble
Hazards
Flash point 297.4 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Eicosadienoic acid (EDA) is a polyunsaturated omega-6 fatty acid with the chemical formula C20H36O2. [3] [4] It is classified as a 20-carbon fatty acid with two double bonds, specifically at the 11th and 14th positions (denoted as 20:2(ω-6)). EDA is a minor fatty acid found in certain animal and plant sources and plays a role in lipid metabolism.

Contents

Properties

Like other polyunsaturated fatty acids (PUFAs) [5] , EDA is hydrophobic and insoluble in water but soluble in organic solvents. It is a precursor for longer-chain omega-6 fatty acids, such as dihomo-gamma-linolenic acid (DGLA) and arachidonic acid (AA). [6]

Isomers

Several isomers are common, all with bonds in the cis-configuration. The omega-6 isomer with bonds in the positions 11 and 14, also known as di-homo-linoleic acid, can be detected in modest concentrations, generally not exceeding 2%, in the seed oils of hundreds of plants, particularly Cruciferae , Ranunculaceae , and Pinaceae , as well as in human breast milk. [7]

The omega-9 isomer with bonds in the positions 5 and 11, also known as keteleeronic acid, can be detected in modest concentrations, generally not exceeding 2%, in the seed oils of Pinaceae and Cupressaceae .

Rarer in the plant world are the isomers with bonds in the positions 6 and 9, or 7 and 11, known as di-homotaxoleic acid.

References

  1. ↑ "SAFETY DATA SHEET" (PDF). Larodan. Retrieved 11 June 2025.
  2. ↑ "cis-11,14-Eicosadienoic acid". Sigma Aldrich . Retrieved 11 June 2025.
  3. ↑ Toldrá, Fidel; Nollet, Leo (8 March 2024). Handbook of Seafood and Seafood Products Analysis. CRC Press. p. 389. ISBN   978-1-003-82543-2 . Retrieved 10 June 2025.
  4. ↑ Riemersma, Rudolph A. (1998). Essential Fatty Acids and Eicosanoids: Invited Papers from the Fourth International Congress. American Oil Chemists' Society. p. 174. ISBN   978-0-935315-96-7 . Retrieved 10 June 2025.
  5. ↑ Manglik, Mr Rohit (12 January 2024). Bioprocess Technology. EduGorilla Publication. p. 1839. ISBN   978-93-6906-153-2 . Retrieved 10 June 2025.
  6. ↑ Sinclair, Andrew; Gibson, Robert (1992). Essential Fatty Acids and Eicosanoids: Invited Papers from the Third International Congress. The American Oil Chemists Society. p. 59. ISBN   978-0-935315-43-1 . Retrieved 10 June 2025.
  7. ↑ "Human Metabolome Database: Showing metabocard for Eicosadienoic acid (HMDB0005060)". hmdb.ca. Retrieved 10 June 2025.
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