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

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

Uses

Used in Pharmaceutical Industry:
Polygodial is used as an analgesic agent for its ability to desensitize sensory neurons, providing pain relief.
Used in Antifungal Applications:
Polygodial is used as an antifungal agent due to its natural ability to inhibit fungal growth, making it a potential candidate for treating fungal infections.
Used in Neurological Research:
Polygodial is used as a TRPA1 activator in neurological research to study the role of TRPA1 channels in pain sensation and other physiological processes.

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

• 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 
• 106540-31-2 (+)-(S)-3-(tert-butyldimethylsiloxy)-2,2-dimethylcyclohexanone 
• 50490-38-5 [(1S,4a5,8a5)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl acetate 

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 
• 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 
• 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 
• 28400-16-0 cinnamolide 

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.

SYNTHESIS OF BIOLOGICALLY ACTIVE DRIMANES FROM (-)-SCLAREOL

The enantiospecific synthesis of drimenyl acetate (8), a key intermediate in the synthesis of biologically active drimanes, and albicanyl acetate (14), potent fish antifeedant, from sclareol (1), are described.Also a short and efficient synthesis of polygodial (22), from albicanyl acetate (14), is shown.

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.

METHODS FOR TREATING CHRONIC FATIGUE SYNDROME AND MYALGIC ENCEPHALOMYELITIS

In one aspect the invention relates to a method of treatment selected from the group consisting of: (a) treating a symptom such as pain in a subject identified or diagnosed as having Myalgic Encephalomyelitis/Chronic Fatigue Syndrome (ME/CFS); (b) treating a symptom such as pain in a subject having dysfunctional TRPM3 ion channel activity; (c) restoring NK cell function in a subject having dysfunctional TRPM3 ion channel activity; and (d) restoring calcium homeostasis in a subject having dysfunctional TRPM3 ion channel activity. The method comprises the step of administering to the subject a therapeutically effective amount of at least one therapeutic compound selected from the group consisting of: (i) an opioid receptor antagonist; (ii) an opioid antagonist; and (iii) a therapeutic compound that restores TRPM3 ion channel activity. In some embodiments the therapeutic compound is naltrexone hydrochloride.

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.

Chemistry of zamoranic acid. Part V. Homochiral semisynthesis of active drimanes: Pereniporin B, polygodial and warburganal

Methyl 14,15-dinor-13-oxo-7-labden-15-oate was obtained from zamoranic acid methyl ester. The former by photochemical cleavage yielded methyl 7,9(11)-drimadien-12-oate, whose chemoselective epoxidation afforded methyl 9α,11-epoxy-7-drimen-12-oate, which is the key synthetic precursor for pereniporin B, polygodial and warburganal.

AN ALTERNATIVE PARTIAL SYNTHESIS OF (-)-POLYGODIAL

A four steps partial synthesis of (-)-polygodial (1) has been achieved, using (-)-drimenol (2) as starting material.

SYNTHESIS OF BOTH THE ENANTIOMERS OF POLYGODIAL, AN INSECT ANTIFEEDANT SESQUITERPENE

Both the natural and unnatural enantiomers of polygodial, an insect antifeedant sesquiterpene of the drimane family, were synthesized starting from (S)-3-hydroxy-2,2-dimethylcyclohexanone as a single chiral source.

Synthesis of all possible stereoisomers of polygodial

The three possible isomers of polygodial, epimers at C-9, cis and trans fused, are described.Controlled kinetic and thermodynamic epimerizations allow preparation of all stereoisomers from the same key intermediate.

Oxo Complexes of Ruthenium(VI) and (VII) as Organic Oxidants

Oxidation of a variety of saturated and unsaturated primary and secondary alcohols by tetraoxoruthenate(VI), 2-, tetraoxoruthenate(VII), -, barium trans-trioxodihydroxoruthenium(VI), trans-Ba, dioxotrichlororuthenate(VI), -, and dioxodichlorobipyridylruthenate(VI),, has been studied; 2- may be used catalytically in conjunction with 2- under basic aqueous conditions.For some of these systems, the oxidation of several aldehydes and amines were also examined.Both 2- and - oxidise primary alcohols to carboxylic acids and secondary alcohols to ketones; the reactivity of these reagents towards unsaturated alcohols was studied in particular.The new species and also cleanly oxidise a wide range of alcohols to aldehydes and ketones without attack of double bonds.Ba functions as a heterogeneous oxidant in dichloromethane, oxidising only the most reactive alcohols to aldehydes.