Sciadonic acid

Source: Wikipedia, the free encyclopedia.
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).

Sciadonic acid, also known as eicosatrienoic acid, is a

biochemical pathways
.

Etymology

The root behind the nomenclature of sciadonic acid comes from its high abundance in the seed, leaves, and wood oils of the plant species Sciadopitys verticillata.[4]

Synthetic methods

There are a few methods reagarding the synthesis of sciadonic acid and other Δ5-fatty acids. One method is through

esterification reaction catalyzed via Lipozyme RM IM and pine nut oil. Lipase-catalyzed esterification reactions leading to the development of Δ5-fatty acids can be achieved in solvent-free conditions using water-jacketed vessel.[6]

Phylogenetic significance in gymnosperms

Sciadonic acid and several other Δ5-olefinic acids are found to be relatively abundant in gymnosperms. Setaria verticillata seeds and their fatty acid compositions allow for distinction between different Coniferophytes such as species from families such as Cupressaceae and Taxodiaceae.[7][8][9] Sciadonic acid is a distinctive fatty acid that shows presence in the oils of seeds, leaves, and woods of conifers. Indicating that plant families can be characterized by the fatty acid composition of their seed, leaves, and wood oils.

Health implications

Eicosanoids and metabolites found to be biologically active have correlated to tumor progression by several mechanisms such as interruption of cell signaling. In humans, fatty acid desaturases, FADS 1,2 and 3 are enzyme coding genes found in chromosome 11q13, in which alterations can be attributed to several types of cancers such as breast, ovarian and cervical cancer. In particular, the FADS2 enzyme, responsible for Δ6 desaturation is no longer functional.[10] In healthy tissues sciadonic acid is usually not within detectable concentrations. However, detectable concentrations have been found in human breast cancer tissues[10] and in pooled human blood plasma.[11] Due to structural similarity, Sciadonic acid has shown potential as a substitute for arachidonic acid in cellular phospholipid pools in signaling pathways.[10] In keratinocytes, sciadonic acids release from the cellular membrane phospholipid pool reduces levels of pro-inflammatory arachidonic acid and the corresponding pro-inflammatory down-stream mediator prostaglandin E2.[12] Reduction of pro-inflammatory mediator molecules also occurs in murine macrophages, regulating the activation of NF-κΒ and MAPK pathways.[12]

References

  1. ^ U.S. National Library of Medicine. (n.d.). Sciadonic acid. National Center for Biotechnology Information. PubChem Compound Database. Retrieved November 10, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/Sciadonic-acid
  2. ^ Sciadonic acid. ChemSpider. (n.d.). Retrieved November 10, 2022, from http://www.chemspider.com/Chemical-Structure.392828.html
  3. ^ U.S. National Library of Medicine. (n.d.). Sciadonic acid. National Center for Biotechnology Information. PubChem Compound Database. Retrieved November 10, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/Sciadonic-acid
  4. S2CID 94058769
    .
  5. ^
    PMID 17384161
    .
  6. PMID 30404964
    .
  7. S2CID 84666529
    .
  8. ^ Wolff, R.L., L.G. Deluc, A.M. Marpeau, and B. Comps, Chemotaxonomic Differentiation of Conifer Families and Genera Based on the Seed Oil Fatty Acid Compositions: Multivariate Analyses, Trees 12:57–65 (1997)
  9. ^ Wolff, R.L., Clarification on the Taxonomic Position of Sciadopitys verticillata Among Coniferophytes Based on the Seed Oil Fatty Acid Compositions, J. Am. Oil Chem. Soc. 75:757–758 (1998)
  10. ^
    PMID 29886893
    .
  11. PMID 37402773
    .
  12. ^
    PMID 22889893
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Sciadonic_acid&oldid=1215134859"