6754-20-7

Basic information

• Product Name: POLYGODIAL
• Synonyms: POLYGODIAL;(-)-Tadeonal;1,2-Naphthalenedicarboxaldehyde, 1,4,4A,5,6,7,8,8A-octahydro-5,5,8A-trimethyl-, (1R-(1alpha,4abeta,8aalpha))-;1,2-Naphthalenedicarboxaldehyde, 1,4,4A,5,6,7,8,8A-octahydro-5,5,8A-trimethyl-, (2R,4as,8as)-;1,2-Naphthalenedicarboxaldehyde, 1alpha,4,4aalpha,5,6,7,8,8A-octahydro-5,5,8abata-trimethyl-;1,4,4A,5,6,7,8,8A-Octahydro-5,5,8A-trimethyl-1,2-naphthalenedicarboxaldehyde;Drim-7-ene-11,12-dial;Poligodial
• CAS NO: 6754-20-7
• Molecular Formula: C₁₅H₂₂O₂
• Molecular Weight: 234.33
• Product Categories: Miscellaneous Natural Products
• Mol File: 6754-20-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 57° (Barnes, Loder)
• Boiling Point: 330.7°Cat760mmHg
• Flash Point: 124°C
• Appearance: white to beige/
• Density: 1.084g/cm³
• Vapor Pressure: 0.000163mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: Store at -20°C
• Solubility: DMSO: soluble20mg/mL, clear
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: POLYGODIAL(CAS DataBase Reference)
• NIST Chemistry Reference: POLYGODIAL(6754-20-7)
• EPA Substance Registry System: POLYGODIAL(6754-20-7)

Safety Data

• Statements: 52/53
• Safety Statements: 61
• WGK Germany: 3
• RTECS: QJ2850000
• Hazardous Substances Data: 6754-20-7(Hazardous Substances Data)

Usage

Description

Polygodial (6754-20-7) is a TRPA1 activator (EC50=400 nM).1?A naturally occurring drimane sesquiterpene dialdehyde found in a variety of plant species including water pepper (Polygonum hydropiper). Polygodial has been used in folk medicine for a variety of indications. Displays analgesic activity via desensitization of sensory neurons.2

Uses

Polygodial is a naturally occurring antifungal and antinociceptive.

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.

References

1) Escalera et al. (2008), TRPA1 mediates the noxious effects of natural sesquiterpene deterrents; J. Biol. Chem., 283 24136 2) Andre et al. (2004), Evidence for the involvement of vanilloid receptor in the antinociception produced by the dialdehydes unsaturated sesquiterpenes polygodial and drimanial in rats; Neuropharmacology, 46 590

InChI: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

Upstream product

• 71557-96-5 dimethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 34437-62-2 drimendiol 
• 106540-41-4 dimethyl (1R,6S,8aR)-1,5,6,7,8,8a-hexahydro-6-hydroxy-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 106540-38-9 dimethyl (6S,8aS)-3,5,6,7,8,8a-hexahydro-6-hydroxy-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 106540-42-5 dimethyl (1R,4aR,6S,8aS)-1,4,4a,5,6,7,8,8a-octahydro-6-hydroxy-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 106622-48-4 dimethyl (1R,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 106540-36-7 dimethyl (6S)-6-t-butyldimethylsilyloxy-3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 106540-43-6 dimethyl (1R,4aS,8aS)-1,4,4a,5,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 106540-33-4 (3S)-3-t-butyldimethylsilyloxy-1-ethynyl-2,2,6-trimethylcyclohexanone 
• 106540-34-5 (S)-4-t-butyldimethylsilyloxy-2-ethynyl-1,3,3-trimethylcyclohexene 
• 106540-35-6 (S)-4-t-butyldimethylsilyloxy-2-vinyl-1,3,3-trimethylcyclohexene 
• 106540-32-3 (3S)-3-t-butyldimethylsilyloxy-2,2,6-trimethylcyclohexanone 
• 106540-40-3 (S)-3-ethenyl-2,2,4-trimethyl-3-cyclohexenol 
• 87655-21-8 (S)-3-hydroxy-2,2-dimethylcyclohexanone 

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 
• 28400-16-0 cinnamolide 
• 644469-20-5 C₃₀H₄₀O₂Si 
• 644469-19-2 C₃₁H₄₄O₂Si 
• 72581-69-2 (-)-(1R,5aS,9aS,9bR)-6,6,9a-trimethyl-1,3,5,5a,6,7,8,9,9a,9b-decahydronaphto[2,1c]furan-1-ol 
• 143813-21-2 (1R,3S,5aS,9aS,9bS)-1,3-Dimethoxy-6,6,9a-trimethyl-9-phenylselanyl-3,5,5a,6,9a,9b-hexahydro-1H-naphtho[1,2-c]furan-7-one 
• 143813-20-1 (1R,3S,5aR,8R,9aS,9bR)-1,3-Dimethoxy-6,6,9a-trimethyl-8-phenylselanyl-3,5,5a,6,8,9,9a,9b-octahydro-1H-naphtho[1,2-c]furan-7-one 
• 16892-20-9 (4aS,8aR)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-2(1H)-naphthalenone 
• 106622-48-4 dimethyl (1R,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate 
• 5956-39-8 Isopolygodial 

Relevant articles and documents

Synthesis of biologically active drimanes and homodrimanes from (-)-sclareol

Three drimanes, polygodial (2), albicanyl acetate (3) and 7-oxo-8,12-drimen-11-al (5), and two homodrimanes, 13,14,15,16-tetranorlabd-7-en-12,17-dial (6) and 7-oxo-13,14,15,16-tetranorlabd-8(17)-en -12-al (7), were synthesized from (-)-sclareol (1), and their antifeedant, antitumor and antimicrobial properties tested. In most cases, 6 and 7 were found to be more active than 2.

Sesquiterpenoid Constituents of Eight Porostome Nudibranchs

Sesquiterpenes of the drimane series were isolated from eight porostome nudibranchs.A mixture of polygodial (1) and olepupuane (3), a new sesquiterpene diacetate, was obtained from Dendrodoris nigra, Dendrodoris tuberculosa, and Dendrodoris krebsii.Olepupuane (3) and the sesquiterpene esters 5 were found in Doriopsilla albopunctata, Doriopsilla janaina, and an undescribed yellow porostome, although one collection of Doriopsilla albopunctata contained only olepupuane (3) while a second collection contained a related methoxy acetal 4.Two undescribed porostomes contained only the sesquiterpene esters 5 found previously in Dendrodoris limbata.The structures of olepupuane (3) and the methoxy acetal 4 are based on interpretation of spectral data.

Diastereoselective ring - Opening of 12-acetoxy-9α and 9β(11)-epoxy-7-drimene: Homochiral semisynthesis of poligodial and warburganal

Starting from a zamoranic acid derivative (Methyl 15-tetrahydropiranyloxy-7-labden-17-oate) poligodial and warburganal have been synthesized in several steps with a 55% overall yield and 27% overall yield, respectively.