Polygodial

Source: Wikipedia, the free encyclopedia.
Polygodial
Names
IUPAC name
Drim-7-ene-11,12-dial
Systematic IUPAC name
(1R,4aS,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde
Other names
Poligodial; Tadeodal; Tadeonal
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13-,15+/m0/s1 ☒N
    Key: AZJUJOFIHHNCSV-KCQAQPDRSA-N ☒N
  • InChI=1/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h5,9-10,12-13H,4,6-8H2,1-3H3/t12-,13-,15+/m0/s1
    Key: AZJUJOFIHHNCSV-KCQAQPDRBV
  • CC1(CCC[C@]2([C@H]1CC=C([C@@H]2C=O)C=O)C)C
Properties
C15H22O2
Molar mass 234.339 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Polygodial is

water-pepper, and Dendrodoris limbata.[1][2][3][4][5]

Chemically it is a

dialdehyde
of formula C15H22O2.

It elicits a warm and pungent flavour.

The

antiallergic activities.[15][16][17]

Polygodial’s primary antifungal action is as a nonionic surfactant, disrupting the lipid-protein interface of integral proteins nonspecifically, denaturing their functional conformation. It is also likely that polygodial permeates by passive diffusion across the plasma membrane, and once inside the cells may react with a variety of intracellular compounds.[18]

It is also an insecticide with antifeedant properties, which causes insects to starve.

References

  1. ISBN 1-86341-902-0
  2. PMID 7089094
    .
  3. doi:10.1016/j.bse.2006.10.019
    .
  4. ^ Jonassohn, Mikael (1996). Sesquiterpenoid unsaturated dialdehydes: structural properties that affect reactivity and bioactivity (PDF) (PhD).
    ISBN 91-628-2215-2. Archived from the original
    (PDF) on 2011-10-03. Retrieved 2008-01-30.
  5. S2CID 8590649
    .
  6. PMID 1775575
    .
  7. PMID 10232062
    .
  8. PMID 11312903
    .
  9. PMID 9714424
    .
  10. PMID 11210140
    .
  11. PMID 3655790
    .
  12. PMID 10604944
    .
  13. PMID 11336250
    .
  14. PMID 10611463
    .
  15. S2CID 206862953
    .
  16. PMID 11787941
    .
  17. PMID 19500663
    .
  18. S2CID 30377678
    .
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