86361-55-9

Basic information

• Product Name: 2-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,3-benzenediol
• Synonyms: 2-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,3-benzenediol;Gnetol;2,3',5',6-Tetrahydroxy-trans-stilbene;-2-(3,5-Dihydroxystyryl)
• CAS NO: 86361-55-9
• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24268
• EINECS: 1312995-182-4
• Mol File: 86361-55-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 271°C(lit.)
• Boiling Point: 540.8 °C at 760 mmHg
• Flash Point: 269.7 °C
• Appearance: /
• Density: 1.468 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.06±0.40(Predicted)
• CAS DataBase Reference: 2-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,3-benzenediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,3-benzenediol(86361-55-9)
• EPA Substance Registry System: 2-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,3-benzenediol(86361-55-9)

Safety Data

• Hazardous Substances Data: 86361-55-9(Hazardous Substances Data)

Usage

Uses

Gnetol (cas# 86361-55-9) is a compound useful in organic synthesis.

Upstream product

• 387-46-2 2,6-dihydroxybenzaldehyde 
• 4670-09-1 2-(3,5-dihydroxyphenyl)acetic acid 
• 3392-97-0 2,6-dimethoxybenzaldehyde 
• 86361-59-3 (E)-1-(2,6-dimethoxyphenyl)-2-(3,5-dimethoxyphenyl)ethene 

Downstream Products

• 86361-58-2 tetraacetoxygnetol 
• 86361-59-3 (E)-1-(2,6-dimethoxyphenyl)-2-(3,5-dimethoxyphenyl)ethene 
• 86361-57-1 dihydrognetol 

Relevant articles and documents

Disparate effects of stilbenoid polyphenols on hypertrophic cardiomyocytes in Vitro vs. in the spontaneously hypertensive heart failure rat

Stilbenoids are bioactive polyphenols, and resveratrol (trans-3,5,40-trihydroxystilbene) is a representative stilbenoid that reportedly exerts cardioprotective actions. As resveratrol exhibits low oral bioavailability, we turned our attention to other stilbenoid compounds with a history of medicinal use and/or improved bioavailability. We determined the effects of gnetol (trans-3,5,20,60-tetrahydroxystilbene) and pterostilbene (trans-3,5-dimethoxy-40-hydroxystilbene) on cardiac hypertrophy. In vitro, gnetol and pterostilbene prevented endothelin-1-induced indicators of cardiomyocyte hypertrophy including cell enlargement and protein synthesis. Gnetol and pterostilbene stimulated AMP-activated protein kinase (AMPK), and inhibition of AMPK, using compound C or shRNA knockdown, abolished these anti-hypertrophic effects. In contrast, resveratrol, gnetol, nor pterostilbene reduced blood pressure or hypertrophy in the spontaneously hypertensive heart failure (SHHF) rat. In fact, AMPK levels were similar between Sprague-Dawley and SHHF rats whether treated by stilbenoids or not. These data suggest that the anti-hypertrophic actions of resveratrol (and other stilbenoids?) do not extend to the SHHF rat, which models heart failure superimposed on hypertension. Notably, SHHF rat hearts exhibited prolonged isovolumic relaxation time (an indicator of diastolic dysfunction), and this was improved by stilbenoid treatment. In conclusion, stilbenoid-based treatment as a viable strategy to prevent pathological cardiac hypertrophy, a major risk factor for heart failure, may be context-dependent and requires further study.

Process for the synthesis of biologically active oxygenated compounds by dealkylation of the corresponding alkylethers

Alkoxy aromatic compounds are conveniently dealkylated to the corresponding phenolic compounds by treatment with aluminum chloride/N,N-dimethyl aniline complex. Aromatic poly O-demethylation is a unique feature of this invention. This process is applicable to the manufacture of polyphenols such as Resveratrol, Oxyresveratrol, Gnetol.