Sciadonic acid

Sciadonic acid
Names
IUPAC name
(5Z,11Z,14Z)-Icosa-5,11,14-trienoic acid
Other names
  • Eicosatrienoic acid
  • 5Z,11Z,14Z-eicosatrienoic acid
  • All-cis-5,11,14-eicosatrienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,15-16H,2-5,8,11-14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,16-15-
    Key: PRHHYVQTPBEDFE-URZBRJKDSA-N
  • CCCCC/C=C\C/C=C\CCCC/C=C\CCCC(=O)O
Properties
C20H34O2
Molar mass 306.490 g·mol−1
Density 0.9 g·cm−3
Boiling point 432 °C (810 °F; 705 K)
log P 7.59
1.489
Hazards
Flash point 329 °C (624 °F; 602 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sciadonic acid, also known as eicosatrienoic acid, is a polyunsaturated fatty acid. In regard to its structure, sciadonic acid has 3 double bonds in the 5, 11, and 14 positions all of which are in the cis configuration. It is further classified as Δ5-fatty, and an omega-6 acid due to the methylene interrupted double bond at carbon-5 and a final double bond 6 carbons away from the methylene tail of the hydrocarbon. Sciadonic acid is a naturally occurring compound and has been found to play a role as a plant metabolite, commonly found in pine nut oil. Furthermore, there have been propositions of several health applications for sciadonic acid as an anti-inflammatory agent. Sharing close structural similarity to arachidonic acid, sciadonic acid acts as a replacement phospholipid in the corresponding biochemical pathways.

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