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Merck
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Principaux documents

SML0049

Sigma-Aldrich

Polygodial

≥97% (HPLC)

Synonyme(s) :

(1R,4aS,8aS)-1,4,4a,5,6,7,8,8a-Octahydro-5,5,8a-trimethyl-1,2-naphthalenedicarboxaldehyde

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About This Item

Formule empirique (notation de Hill):
C15H22O2
Numéro CAS:
6754-20-7
Poids moléculaire :
234.33
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Essai

≥97% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 20 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

O=C[C@@H]1[C@@]2([C@H](C(CCC2)(C)C)CC=C1C=O)C

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

Clé InChI

AZJUJOFIHHNCSV-KCQAQPDRSA-N

Actions biochimiques/physiologiques

Polygodial is a selective activator of Transient Receptor Potential Anykrin 1 (TRPA1) channels. Initially painful, polygodial acts as an analgesic by desensitizing sensory neuron. Polygodial also has broad antifungal properties, and is cytotoxic against bacteria and algae.
Polygodial is a sesquiterpene dialdehyde. It is obtained from the plants Polygonum hydropiper, Warburgia ugandensis, Pseudowintera colorata and Warburgia stuhlmannii. It exhibits antifeedant activity and antimicrobial activity against insects and microbes, respectively. It is responsible for the “hot taste” in peppery spices of traditional Japanese cuisine.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000216450
0000216449
116M4741V
024M4722V

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Consulter la Bibliothèque de documents

Ken-ichi Fujita et al.
Bioorganic & medicinal chemistry, 13(24), 6742-6747 (2005-08-27)
The antifungal activity of polygodial against Saccharomyces cerevisiae involves multifunctions. Polygodial first acts as a surface-active agent (surfactant) and then becomes involved in biochemical processes. The ability to form a pyrrole derivative with a primary amine group of phosphatidylethanolamine (PE)
Ken-Ichi Fujita et al.
Journal of chemical ecology, 29(10), 2253-2262 (2003-12-20)
A bicyclic sesquiterpene dialdehyde, polygodial did not inhibit root elongation up to a concentration of 12.5 microg/ml in a lettuce seedling assay: trans-Cinnamic acid inhibited the elongation by 50% at 1.2 microg/ml (8.1 microM). The inhibitory activity of trans-cinnamic acid
Juntaro Nakajima et al.
Journal of digestive diseases, 8(1), 48-51 (2007-01-31)
To isolate, identify and determine the prevalence of yeasts in the oral cavity of individuals and to test the minimum inhibitory dilution (MID) of Kolorex against the yeasts isolated. Twenty-nine individuals of both sexes aged on average 61.3 years were
Eunice Andre et al.
Neuropharmacology, 46(4), 590-597 (2004-02-21)
This study investigated whether or not the neonatal treatment of rats with the sesquiterpenes polygodial or drimanial could cause persistent antinociception similar to that induced by capsaicin. Rats were injected subcutaneously 48 h after birth with capsaicin (50 mg/kg), polygodial
Luis Moreno-Osorio et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 63(3-4), 215-220 (2008-06-07)
Polygodial (1) and its derivatives acetal 2 (propylene) and 3 (ethylene) were prepared and their antifeedant activity and toxic effects evaluated on several insect species with different feeding ecologies (Spodoptera littoralis, Leptinotarsa decemlineata, Myzus persicae and Rhopalosiphum padi) along with
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