| Name: | (1R,4aS,8aS)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde |
| CAS Number: | 6754-20-7 |  3D/inchi
|
| FDA UNII: | 5FAF7T66M7 |
| MDL: | MFCD00238664 |
| XlogP3-AA: | 3.20 (est) |
| Molecular Weight: | 234.33874000 |
| Formula: | C15 H22 O2 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 330.00 to 331.00 °C. @ 760.00 mm Hg (est)
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| Vapor Pressure: | 0.000163 mmHg @ 25.00 °C. (est) |
| Flash Point: | 255.00 °F. TCC ( 124.00 °C. ) (est)
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| logP (o/w): | 3.522 (est) |
| Soluble in: |
| | alcohol | | | water, 44.52 mg/L @ 25 °C (est) |
| Insoluble in: |
| | water |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for (-)-polygodial usage levels up to: | | | not for fragrance use.
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| |
| Recommendation for (-)-polygodial flavor usage levels up to: |
| | not for flavor use.
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Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :72503 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (1R,4aS,8aS)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde |
| Chemidplus:0000469670 |
| RTECS:QJ2850000 for cas# 6754-20-7 |
References:
| | (1R,4aS,8aS)-5,5,8a-trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 72503 |
| Pubchem (sid): | 135214272 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | drim-7-ene-11,12-dial | | 7-11,12- | drimene dial | | 1alpha,4,4aalpha,5,6,7,8,8a- | octahydro-5,5,8abata-trimethyl-1,2-naphthalene dicarboxaldehyde | | | polygodial | | (-)- | tadeonal | | (1R,4aS,8aS)-5,5,8a- | trimethyl-1,4,4a,6,7,8-hexahydronaphthalene-1,2-dicarbaldehyde |
Articles:
| PubMed:Comparison of the chemical composition of three species of smartweed (genus Persicaria) with a focus on drimane sesquiterpenoids. |
| PubMed:Study on the Cytotoxic Activity of Drimane Sesquiterpenes and Nordrimane Compounds against Cancer Cell Lines. |
| PubMed:Polygodial: a contact active antifouling biocide. |
| PubMed:Antioxidant and α-amylase inhibitory activities of extract and isolates from Zygogynum pancheri subsp. arrhantum. |
| PubMed:Anethole induces apoptotic cell death accompanied by reactive oxygen species production and DNA fragmentation in Aspergillus fumigatus and Saccharomyces cerevisiae. |
| PubMed:The pungent substances piperine, capsaicin, 6-gingerol and polygodial inhibit the human two-pore domain potassium channels TASK-1, TASK-3 and TRESK. |
| PubMed:Prophylactic strategies in recurrent vulvovaginal candidiasis: a 2-year study testing a phytonutrient vs itraconazole. |
| PubMed:Medicinal plants of Chile: evaluation of their anti-Trypanosoma cruzi activity. |
| PubMed:Laboratory assessment of the antifouling potential of a soluble-matrix paint laced with the natural compound polygodial. |
| PubMed:Comparative antifeedant activities of polygodial and pyrethrins against whiteflies (Bemisia tabaci) and aphids (Myzus persicae). |
| PubMed:Screening for antioxidant and detoxification responses in Perna canaliculus Gmelin exposed to an antifouling bioactive intended for use in aquaculture. |
| PubMed:Comparative study on the larvicidal activity of drimane sesquiterpenes and nordrimane compounds against Drosophila melanogaster til-til. |
| PubMed:Drimanes from Drimys brasiliensis with leishmanicidal and antimalarial activity. |
| PubMed:Chemical constituents derived from Drimys brasiliensis Miers (Winteraceae). |
| PubMed:Drimendiol, a drimane sesquiterpene with quorum sensing inhibition activity. |
| PubMed:Structural requirements for the antifungal activities of natural drimane sesquiterpenes and analogues, supported by conformational and electronic studies. |
| PubMed:Screening for negative effects of candidate ascidian antifoulant compounds on a target aquaculture species, Perna canaliculus Gmelin. |
| PubMed:Distribution of drimane sesquiterpenoids and tocopherols in liverworts, ferns and higher plants: Polygonaceae, Canellaceae and Winteraceae species. |
| PubMed:Red leaf margins indicate increased polygodial content and function as visual signals to reduce herbivory in Pseudowintera colorata. |
| PubMed:Preventing ascidian fouling in aquaculture: screening selected allelochemicals for anti-metamorphic properties in ascidian larvae. |
| PubMed:Protective effect of an oral natural phytonutrient in recurrent vulvovaginal candidiasis: a 12-month study. |
| PubMed:Exploring natural products for new taste sensations. |
| PubMed:Morphological changes of the filamentous fungus Mucor mucedo and inhibition of chitin synthase activity induced by anethole. |
| PubMed:Evidence for involvement of TRPA1 in the detection of vibrations by hair bundle mechanoreceptors in sea anemones. |
| PubMed:Anti-leishmanial and anti-trypanosomal potential of polygodial isolated from stem barks of Drimys brasiliensis Miers (Winteraceae). |
| PubMed:Drug-induced permeabilization of S. cerevisiae. |
| PubMed:Chemotaxonomy of Pseudowintera: sesquiterpene dialdehyde variants are species markers. |
| PubMed:Ugandenial A, a new drimane-type sesquiterpenoid from Warburgia ugandensis. |
| PubMed:Influence of plant part, season of collection and content of the main active constituent, on the antifungal properties of Polygonum acuminatum Kunth. |
| PubMed:Sesquiterpene dialdehydes inhibit MSU crystal-induced superoxide production by infiltrating neutrophils in an in vivo model of gouty inflammation. |
| PubMed:Miogadial and miogatrial with alpha,beta-unsaturated 1,4-dialdehyde moieties--novel and potent TRPA1 agonists. |
| PubMed:Cytotoxic sesquiterpenoids from Winteraceae of Caledonian rainforest. |
| PubMed:Mioganal, a novel pungent principle in myoga (Zingiber mioga Roscoe) and a quantitative evaluation of its pungency. |
| PubMed:TRPA1 mediates the noxious effects of natural sesquiterpene deterrents. |
| PubMed:Antifeedant activity of some polygodial derivatives. |
| PubMed:Secondary metabolites of Cinnamosma madagascariensis and their alpha-glucosidase inhibitory properties. |
| PubMed:From labdanes to drimanes. Degradation of the side chain of dihydrozamoranic acid. |
| PubMed:Enantioselective synthesis and vanilloid activity evaluation of 1-beta-(p-methoxycinnamoyl)polygodial, an antinociceptive compound from Drymis winteri barks. |
| PubMed:Naturally occurring compounds affect glutamatergic neurotransmission in rat brain. |
| PubMed:Effect of a novel phyto-compound on mucosal candidiasis: further evidence from an ex vivo study. |
| PubMed:Drimanes and other terpenoids from the fern Thelypteris hispidula (Decne.) Reed. |
| PubMed:Anethole, a potential antimicrobial synergist, converts a fungistatic dodecanol to a fungicidal agent. |
| PubMed:A novel labdane-type trialdehyde from myoga (Zingiber mioga Roscoe) that potently inhibits human platelet aggregation and human 5-lipoxygenase. |
| PubMed:Native Kenyan plants as possible alternatives to methyl bromide in soil fumigation. |
| PubMed:Phytochemistry and antifungal properties of the newly discovered tree Pleodendron costaricense. |
| PubMed:The sesquiterpenes polygodial and drimanial in vitro affect glutamatergic transport in rat brain. |
| PubMed:Comparison of volatile constituents of Persicaria odorata(Lour.) Soják (Polygonum odoratum Lour.) and Persicaria hydropiper L. Spach (Polygonum hydropiper L.). |
| PubMed:Subchronic toxicity study of water pepper extract in F344 rats. |
| PubMed:Pharmacological characterisation of the plant sesquiterpenes polygodial and drimanial as vanilloid receptor agonists. |
| PubMed:Preventive strategy for Candida gut translocation during ischemia-reperfusion injury supervening on protein-calorie malnutrition. |
| PubMed:Antibacterial activity of polygodial. |
| PubMed:Depletion of glutathione as a cause of the promotive effects of polygodial, a sesquiterpene on the production of reactive oxygen species in Saccharomyces cerevisiae. |
| PubMed:Antifungal activity of drimane sesquiterpenes from Drimys brasiliensis using bioassay-guided fractionation. |
| PubMed:Multifunctional action of antifungal polygodial against Saccharomyces cerevisiae: involvement of pyrrole formation on cell surface in antifungal action. |
| PubMed:Naturally occurring antifungal agents against Zygosaccharomyces bailii and their synergism. |
| PubMed:In view of an optimal gut antifungal therapeutic strategy: an in vitro susceptibility and toxicity study testing a novel phyto-compound. |
| PubMed:Inhibition of the mitochondrial ATP synthesis by polygodial, a naturally occurring dialdehyde unsaturated sesquiterpene. |
| PubMed:Effect of EDTA alone and in combination with polygodial on the growth of Saccharomyces cerevisiae. |
| PubMed:A complete 1H and 13C NMR data assignment for four drimane sesquiterpenoids isolated from Drimys winterii. |
| PubMed:Screening for microtubule-disrupting antifungal agents by using a mitotic-arrest mutant of Aspergillus nidulans and novel action of phenylalanine derivatives accompanying tubulin loss. |
| PubMed:Evidence for the involvement of vanilloid receptor in the antinociception produced by the dialdeydes unsaturated sesquiterpenes polygodial and drimanial in rats. |
| PubMed:Synergism of polygodial and trans-cinnamic acid on inhibition of root elongation in lettuce seedling growth bioassays. |
| PubMed:Synthesis and in vitro trypanocide activity of several polycyclic drimane-quinone derivatives. |
| PubMed:Protective effects of polygodial on gastric mucosal lesions induced by necrotizing agents in rats and the possible mechanisms of action. |
| PubMed:Role of nitric oxide and K+ channels in relaxation induced by polygodial in rabbit corpus cavernosum in vitro. |
| PubMed:Protective effects of polygodial and related compounds on ethanol-induced gastric mucosal lesions in rats: structural requirements and mode of action. |
| PubMed:Additional evidence for the anti-inflammatory and anti-allergic properties of the sesquiterpene polygodial. |
| PubMed:Naturally occurring anti-Salmonella agents. |
| PubMed:Occurrence of polygodial and 1-(2,4,6-trimethoxyphenyl)-but-2-en-1-one from some ferns and liverworts: role of pungent components in bryophytes and pteridophytes evolution. |
| PubMed:Polygodial, the fungitoxic component from the Brazilian medicinal plant Polygonum punctatum. |
| PubMed:A sesquiterpene drimane with antinociceptive activity from Drimys winteri bark. |
| PubMed:Antifungal mechanism of polygodial. |
| PubMed:Synthesis of (+)-cyclozonarone and the absolute configuration of naturally occurring (-)-cyclozonarone. |
| PubMed:Polygodial, a potent attachment-inhibiting substance for the blue mussel, Mytilus edulis galloprovincialis from Tasmannia lanceolata. |
| PubMed:Effect of polygodial on the mitochondrial ATPase of Saccharomyces cerevisiae. |
| PubMed:Action of polygodial on agonist-induced contractions of the rat portal vein in vitro. |
| PubMed:Mechanisms underlying the relaxation caused by the sesquiterpene polygodial in vessels from rabbit and guinea-pig. |
| PubMed:Assessment of mechanisms involved in antinociception caused by sesquiterpene polygodial. |
| PubMed:In vitro antifungal susceptibilities of Candida albicans and other fungal pathogens to polygodial, a sesquiterpene dialdehyde. |
| PubMed:Isolation and identification of active compounds from Drimys winteri barks. |
| PubMed:Polygodial Inhibits Carbachol-induced Muscarinic Acetylcholine Receptor Signal Transduction. |
| PubMed:Anti-hyperalgesic properties of the extract and of the main sesquiterpene polygodial isolated from the barks of Drymis winteri (Winteraceae). |
| PubMed:Action of polygodial, a sesquiterpene isolated from Drymis winteri, in the guinea-pig ileum and trachea 'in vitro'. |
| PubMed:Polygodial-induced noradrenaline release in human neuroblastoma SH-SY5Y cells. |
| PubMed:Polygodial induces inositol phosphate turnover in human neuroblastoma SH-SY5Y cells. |
| PubMed:Sesquiterpenoid unsaturated dialdehydes increase the concentration of intracellular free Ca2+ in human neuroblastoma SH-SY5Y cells. |
| PubMed:Potentiation of antifungal activity of sesquiterpene dialdehydes against Candida albicans and two other fungi. |
| PubMed:The effect of six sesquiterpenoid unsaturated dialdehydes on cell membrane permeability in human neuroblastoma SH-SY5Y cells. |
| PubMed:Antimicrobial agents from Licaria puchuri-major and their synergistic effect with polygodial. |
| PubMed:Comparison of the antimicrobial and cytotoxic activities of twenty unsaturated sesquiterpene dialdehydes from plants and mushrooms. |
| PubMed:The cytotoxicity of 22 sesquiterpenoid unsaturated dialdehydes, as determined by the neutral red absorption assay and by protein determination. |
| PubMed:Synthesis of antifeedants for insects: novel behaviour-modifying chemicals from plants. |
| PubMed:Activity of drimane antifeedants and related compounds against aphids, and comparative biological effects and chemical reactivity of (-)- and (+)-polygodial. |
| PubMed:Occurrence of olepupuane in two mediterranean nudibranchs: a protected form of polygodial. |
| PubMed:Polygodial, an antifungal potentiator. |
| PubMed:Insect antifeedant activity and hot taste for humans of selected natural and synthetic 1,4-dialdehydes. |
| PubMed:Dorid nudibranch elaborates its own chemical defense. |
| PubMed:Antibiotic substances from New Zealand plants. II. Polygodial, an anti-Candida agent from Pseudowintera colorata. |
| PubMed:Stereospecificity of allergic contact dermatitis (ACD) to enantiomers. Part III. experimentally induced ACD to a natural sesquiterpene dialdehyde, polygodial in guinea pigs. |
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