Polygodial

Polygodial
Names

IUPAC name (1R,4aS,8aS)-5,5,8a-Trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarboxaldehyde
Other names Poligodial; Tadeodal; Tadeonal; Drim-7-ene-11,12-dial
Identifiers
CAS Number	6754-20-7^Y
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL254550^N
ChemSpider	65414^N
PubChem	72503
InChI 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
SMILES CC1(CCC[C@]2([C@H]1CC=C([C@@H]2C=O)C=O)C)C
Properties
Chemical formula	C₁₅H₂₂O₂
Molar mass	234.33398
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Polygodial is an active constituent of Dorrigo Pepper, Mountain Pepper, Horopito, Canelo, Paracress and Water-pepper. Furthermore, Polygodial is synthetized by Dendrodoris limbata.

Chemically it is a drimane-type sesquiterpene dialdehyde of formula C₁₅H₂₂O₂.

It elicits a warm and pungent flavour.

The biological activity of polygodial has been reported in the scientific literature to include antifungal and antimicrobial activities, antihyperalgesia, potent attachment-inhibitory activity, insect antifeedant activity,antinociception vasorelaxation action in vessels of rabbit and guinea pig,anti-inflammatory and antiallergic activities

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.

It is also used as an insecticide for its antifeedant property, which causes insects to starve.

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Wikipedia