5956-39-8

Basic information

• Product Name: EPIPOLYGODIAL
• Synonyms: EPIPOLYGODIAL;[(1S)-1,4,4aα,5,6,7,8,8a-Octahydro-5,5,8aβ-trimethylnaphthalene]-1α,2-dicarbaldehyde;Isopolygodial
• CAS NO: 5956-39-8
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33
• Mol File: 5956-39-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 330.7°C at 760 mmHg
• Flash Point: 124°C
• Appearance: /
• Density: 1.094g/cm³
• Vapor Pressure: 0.000163mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: EPIPOLYGODIAL(CAS DataBase Reference)
• NIST Chemistry Reference: EPIPOLYGODIAL(5956-39-8)
• EPA Substance Registry System: EPIPOLYGODIAL(5956-39-8)

Safety Data

• Hazardous Substances Data: 5956-39-8(Hazardous Substances Data)

Usage

Uses

Epipolygodial has been shown to be effective against drug resistant cancer cells and other proliferative diseases.

InChI:InChI=1/C15H22O2/c1-14(2)7-4-8-15(3)12(10-17)11(9-16)5-6-13(14)15/h9-10,13H,4-8H2,1-3H3/t13?,15-/m0/s1

Upstream product

• 361544-76-5 5,5,8a-Trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1,2-dicarboxylic acid dimethyl ester 
• 71558-02-6 Dimethoxy carbonyl-1,2 trimethyl-5,5,8a Octahydro-1,4,4a,5,6,7,8,8a naphtalene-(1RS, 4aSR, 8aRS) 
• 22567-27-7 ((1S,4aR,8aS)-2-Hydroxymethyl-5,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-methanol 
• 71557-96-5 dimethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 5956-39-8 (1S,4aR,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde 
• 6754-20-7 Polygodial 
• 83630-99-3 pu'ulenal 
• 79679-67-7 (S)-5,5,8a-Trimethyl-1,5,6,7,8,8a-hexahydro-naphthalene-1,2-dicarboxylic acid dimethyl ester 
• 71558-02-6 (1S,4aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarboxylic acid dimethyl ester 

Downstream Products

• 5956-39-8 (1R,4aR,8aS)-5,5,8a-Trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1,2-dicarbaldehyde 
• 16892-20-9 (4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-2(1H)-naphthalenone 

Relevant articles and documents

Structure-Pungency Relationships and TRP Channel Activation of Drimane Sesquiterpenes in Tasmanian Pepper (Tasmannia lanceolata)

Sensory-guided fractionation of extracts of Tasmanian pepper berries revealed 20 drimane sesquiterpens, among which polygodial, warburganal, and 1β-acetoxy-9-deoxy-isomuzigadial exhibited the lowest pungency threshold concentrations on the tongue surface (0.6-2.8 nmol/cm2) and elicited a dose-dependent calcium influx into mTRPA1 expressing CHO cells with the lowest EC50 values (4.5 ± 1.0 to 16.7 ± 7.5 μmol/L) and a good correlation to oral pungency thresholds (R2 = 0.986, linear regression). Calcium imaging assays demonstrated these chemosensates to induce a calcium influx into cultured trigeminal neurons prepared from wildtype (TRPA1+/+) mice, whereas no calcium influx was observed in neurons from TRPA1 knockout mice (TRPA1-/-), thus confirming the α,β-unsaturated 1,4-dialdehyde structure to be the required structural motif for a low oral puncency thresholds and activation of the Transient Receptor Potential Channel A1 (TRPA1). Time-resolved NMR experiments confirmed the pungency mediating mechanism for electrophilic drimane sesquiterpene dialdehydes to be different from that found for other electrophilic pungent agents like isothiocyanates, which have been shown to undergo a covalent binding with cysteine residues in TRPA1. Instead, the high-impact chemosensates polygodial, warburganal, and 1β-acetoxy-9-deoxy-isomuzigadial showed immediate reactivity with the ?-amino group of lysine side chains to give pyrrole-type conjugates, thus showing evidence for TRPA1 activation by covalent lysine modification.

DEFENSE ALLOMONES OF SOME MARINE MOLLUSKS

Certain marine mollusks that lack obvious physical protection have evolved various biological and chemical defense strategies.One type of chemical defense involves accumulation of small organic molecules largely from the diet, which afford protection from common predators.Our work and research by others has shown that the animals can utilize different structural types.Interestingly several of the defense allomones which have been defined are structurally related to the drimane sesquiterpenoids which have been shown to be antifeedants against terrestrial insects.

Activity of natural and synthetic polygodial derivatives against Trypanosoma cruzi amastigotes, trypomastigotes and epimastigotes

Our laboratories have been investigating biological effects of a sesquiterpenoid polygodial and its natural and synthetic analogues. Herein, we report the evaluation of these compounds against the three forms of Trypanosoma cruzi, amastigotes, trypomastigotes and epimastigotes. Although polygodial was found to be poorly active, its natural congener epipolygodial and synthetic Wittig-derived analogues showed low micromolar potency against all three forms of the parasite. Synthetic α,β-unsaturated phosphonate 9 compared favorably with clinically approved drugs benznidazole and nifurtimox, and was effective against trypomastigotes, toward which benznidazole showed no activity. (Figure presented.).

Probing the Structure-Activity Relationship of the Natural Antifouling Agent Polygodial against both Micro- and Macrofoulers by Semisynthetic Modification

The current study represents the first comprehensive investigation into the general antifouling activities of the natural drimane sesquiterpene polygodial. Previous studies have highlighted a high antifouling effect toward macrofoulers, such as ascidians, tubeworms, and mussels, but no reports about the general antifouling effect of polygodial have been communicated before. To probe the structural and chemical basis for antifouling activity, a library of 11 polygodial analogues was prepared by semisynthesis. The library was designed to yield derivatives with ranging polarities and the ability to engage in both covalent and noncovalent interactions, while still remaining within the drimane sesquiterpene scaffold. The prepared compounds were screened against 14 relevant marine micro- and macrofouling species. Several of the polygodial analogues displayed inhibitory activities at sub-microgram/mL concentrations. These antifouling effects were most pronounced against the macrofouling ascidian Ciona savignyi and the barnacle Balanus improvisus, with inhibitory activities observed for selected compounds comparable or superior to several commercial antifouling products. The inhibitory activity against the microfouling bacteria and microalgae was reversible and significantly less pronounced than for the macrofoulers. This study illustrates that the macro- and microfoulers are targeted by the compounds via different mechanisms.