70677-47-3

Basic information

• Product Name: 3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol
• Synonyms: 3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol;Canniprene
• CAS NO: 70677-47-3
• Molecular Formula: C₂₁H₂₆O₄
• Molecular Weight: 342.43
• Mol File: 70677-47-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 500.3±45.0 °C(Predicted)
• Appearance: /
• Density: 1.128±0.06 g/cm3(Predicted)
• PKA: 9.63±0.10(Predicted)
• CAS DataBase Reference: 3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol(70677-47-3)
• EPA Substance Registry System: 3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol(70677-47-3)

Safety Data

• Hazardous Substances Data: 70677-47-3(Hazardous Substances Data)

Usage

General Description

3-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-6-methoxy-2-(3-methyl-2-butenyl)phenol, also known as Icariside II, is a naturally occurring chemical compound found in the herb Epimedium brevicornum. It is classified as a prenylated flavonoid and has been shown to possess various biological activities, including anti-inflammatory, anti-oxidative, and neuroprotective effects. It is also known to have potential therapeutic effects in the treatment of cardiovascular diseases, osteoporosis, and as an aphrodisiac. Its complex chemical structure and diverse pharmacological properties make it an interesting target for further research and development in the field of natural products-based drug discovery.

Upstream product

• 76735-51-8 Benzoic acid 3-{2-[3-hydroxy-4-methoxy-2-(3-methyl-but-2-enyl)-phenyl]-ethyl}-5-methoxy-phenyl ester 
• 83088-11-3 3',5-dibenzyloxy-3,4'-dimethoxy-2'-(3-methylbut-2-enyl)stilbene 
• 621-59-0 isovanillin 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 50637-28-0 (3-(benzyloxy)-5-methoxyphenyl)methanol 
• 19520-74-2 3-hydroxy-5-methoxy-benzoic acid methyl ester 
• 50637-26-8 methyl 3-(benzyloxy)-5-methoxybenzoate 
• 76735-46-1 3'-benzyloxy-5-hydroxy-3,4'-dimethoxystilbene 
• 76735-49-4 5-benzoyloxy-3'-hydroxy-3,4'-dimethoxydihydrostilbene 
• 76735-50-7 Benzoic acid 3-{2-[3-(1,1-dimethyl-allyloxy)-4-methoxy-phenyl]-ethyl}-5-methoxy-phenyl ester 
• 76735-48-3 Benzoic acid 3-{2-[3-(1,1-dimethyl-prop-2-ynyloxy)-4-methoxy-phenyl]-ethyl}-5-methoxy-phenyl ester 
• 76735-47-2 Benzoic acid 3-[(E)-2-(3-benzyloxy-4-methoxy-phenyl)-vinyl]-5-methoxy-phenyl ester 
• 91925-81-4 3-(bromomethyl)-5-methoxyphenol 
• 83088-09-9 3-hydroxy-4-methoxy-2-(3-methylbut-2-enyl)benzaldehyde 

Downstream Products

• 70677-43-9 canniprene chroman 
• 70677-42-8 dihydrocanniprene 
• 70677-45-1 Acetic acid 3-[2-(3-acetoxy-5-methoxy-phenyl)-ethyl]-6-methoxy-2-(3-methyl-but-2-enyl)-phenyl ester 
• 70677-46-2 1-[2-(3,5-Dimethoxy-phenyl)-ethyl]-3,4-dimethoxy-2-(3-methyl-but-2-enyl)-benzene 
• 70677-44-0 Acetic acid 3-methoxy-5-[2-(8-methoxy-2,2-dimethyl-chroman-5-yl)-ethyl]-phenyl ester 
• 71135-74-5 5-(3,5-dimethoxyphenylethyl)-3,4-dihydroxy-8-methoxy-2,2-dimethyl-2H-chromen 

Relevant articles and documents

Dihydrostilbenes of Cannabis. Synthesis of Canniprene

Canniprene (10) is synthesised via reaction of a phenolate-anion ylide with a benzyl-protected aldehyde.Benzoylation, followed by hydrogenation and hydrogenolysis of the resulting stilbene, leads to a half-benzoylated bibenzyl which is converted into its O-dimethylprop-2-ynyl derivative.Semi-hydrogenation, Claisen rearrangement, and debenzoylation gives canniprene.In a second synthesis the prenylated (3-methylbut-2-enylated) and benzyl-protected ring-B section is made first and converted by Wittig reaction into a dibenzyl-protected stilbene.The stilbene is reduced and the benzyl groups removed in one step, without affecting the prenyl group, by sodium in butanol: magnesium in methanol is capable of stilbene reduction without debenzylation.This practical synthesis proceeds in 19 percent overall yield from the dimethylprop-2-ynyl ether of isovanillin (14) and is applicable to isotopelabelling.The use of p-bromophenacyl (PBP) ether and methoxyethoxymethyl (MEM) ether protection as the basis for canniprene synthesis is also considered.Other bibenzyls relevant to the natural products of Cannabis are made and the methylated chroman (37) derived from canniprene is also synthesised.