78919-28-5

Basic information

• Product Name: 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol
• Synonyms: (2R,3S,4R,5R)-(+)-Chicanine;4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol;Chicanine;Chicanin
• CAS NO: 78919-28-5
• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.38568
• Mol File: 78919-28-5.mol

Chemical Properties

• Boiling Point: 483.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• PKA: 9.91±0.35(Predicted)
• CAS DataBase Reference: 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol(78919-28-5)
• EPA Substance Registry System: 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol(78919-28-5)

Safety Data

• Hazardous Substances Data: 78919-28-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol is used as a pharmaceutical compound for its potential therapeutic effects. The specific arrangement of its stereocenters and the presence of bioactive functional groups may contribute to its interaction with biological targets, making it a candidate for the development of new drugs.
Used in Antiviral Applications:
In the pharmaceutical industry, 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol is used as an antiviral agent. It has shown moderate inhibition of herpes simplex virus-2 and adenovirus in human hepatocellular carcinoma and African green monkey kidney cell lines, indicating its potential use in the development of antiviral medications.
Used in Drug Delivery Systems:
4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol can also be used in the development of drug delivery systems. Its unique structure and functional groups may allow for the design of targeted drug delivery systems, improving the bioavailability and therapeutic outcomes of the compound.
Used in Chemical Synthesis:
In the chemical industry, 4-[(2R,3S,4R,5R)-5-(1,3-Benzodioxol-5-yl)tetrahydro-3,4-dimethyl-2-furanyl]-2-methoxyphenol may be used as a building block or intermediate in the synthesis of more complex molecules. Its unique structure and functional groups can be exploited to create a variety of novel compounds with potential applications in various fields.

Upstream product

• 1310802-58-4 (S)-4-benzyl-3-((2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-3-hydroxy-2-methylpropanoyl)oxazolidin-2-one 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1310802-59-5 (((1S,2R)-1-(4-(benzyloxy)-3-methoxyphenyl)-2,3-dimethylbut-3-en-1-yl)oxy)(tert-butyl)dimethylsilane 
• 1310802-65-3 (3S,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-3-methylbutan-2-one 
• 1310802-64-2 C₂₅H₃₈O₄Si 
• 1310802-63-1 (2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-methylpropanal 
• 1310802-62-0 C₃₄H₄₃NO₆Si 
• 1310802-75-5 4-((2S,3R,4S,5S)-5-(benzo[d][1,3]dioxol-5-yl)-3,4-dimethyltetrahydrofuran-2-yl)-2-methoxyphenyl 4-methylbenzenesulfonate 
• 1310802-74-4 C₂₇H₂₆O₆ 
• 1310802-72-2 C₂₇H₂₈O₅ 
• 1310802-70-0 C₂₇H₂₈O₇ 
• 1310802-78-8 C₃₃H₄₂O₇Si 
• 1310802-69-7 C₂₆H₃₈O₆Si 
• 1310802-61-9 C₂₇H₃₀O₆ 

Downstream Products

• 78919-29-6 chicanine acetate 
• 54473-24-4 4-(4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutyl)benzene-1,2-diol 
• 117142-10-6 desoxydemethylenechicanine 
• 114761-92-1 Macelignan 
• 59985-35-2 desoxyenshicine 
• 78868-99-2 6,6''-dinitrochicanine ethyl ether 
• 3738-02-1 (+) galcatin 
• 78869-00-8 (7'R,8'S)-7'-(3',4'-dimethoxyphenyl)-8,8'-dimethyl-7',8'-dihydronaphtho[4,5-d][1,3]dioxole 

Relevant articles and documents

Systematic Asymmetric Synthesis of All Diastereomers of (-)-Talaumidin and Their Neurotrophic Activity

(-)-Talaumidin (1), a 2,5-biaryl-3,4-dimethyltetrahydrofuran lignan isolated from Aristolochia arcuata Masters, shows significant neurite-outgrowth promotion and neuroprotection in primary cultured rat cortical neurons and in NGF-differentiated PC12 cells

Asymmetric synthesis of (-)-chicanine using a highly regioselective intramolecular Mitsunobu reaction and revision of its absolute configuration

First asymmetric synthesis of (-)-chicanine has been accomplished in 14 steps by employing the Evans asymmetric syn-selective aldol reaction, diastereoselective hydroboration and an regioselective, intramolecular Mitsunobu etherification. The absolute configuration of (+)- and (-)-chicanine has been revised to 2R,3S,4R,5R and 2S,3R,4S,5S, respectively, through CD analysis.