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Key Documents

SML0049

Sigma-Aldrich

Polygodial

≥97% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C15H22O2
CAS Number:
6754-20-7
Molecular Weight:
234.33
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°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

InChI key

AZJUJOFIHHNCSV-KCQAQPDRSA-N

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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