63644-71-3

Basic information

• Product Name: γ-Methoxyisoeugenol
• Synonyms: γ-Methoxyisoeugenol;2-Methoxy-4-(3-methoxy-1-propenyl)phenol;gamma-Methoxyisoeugenol
• CAS NO: 63644-71-3
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.22706
• Mol File: 63644-71-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: γ-Methoxyisoeugenol(CAS DataBase Reference)
• NIST Chemistry Reference: γ-Methoxyisoeugenol(63644-71-3)
• EPA Substance Registry System: γ-Methoxyisoeugenol(63644-71-3)

Safety Data

• Hazardous Substances Data: 63644-71-3(Hazardous Substances Data)

Usage

General Description

γ-Methoxyisoeugenol, also known as 4-Methoxy-3-propen-2-ylphenol, is a natural organic compound often used in scientific research due to its biological activity. Its molecular formula is C10H12O2 and it is soluble in water, ether, and alcohol. γ-Methoxyisoeugenol is a derivative of Phenol and is formed by removing a hydrogen atom from the aromatic ring. The compound has shown strong antimicrobial activities against certain bacteria, making it potentially useful in fields like medicine and pharmacology. However, as with all chemicals, appropriate protective measures should be taken when handling γ-Methoxyisoeugenol to avoid unnecessary exposure and risk.

Upstream product

• 97-53-0 4-allylguaiacol 
• 7382-59-4 guaiacylglycerol-β-guaiacyl ether 
• 458-35-5 coniferol 
• 67-56-1 methanol 
• 129664-76-2 2-methoxy-4-(2-propenylidene)-2,5-cyclohexadien-1-one, Z-isomer 
• 63644-62-2 (E,E)-3-(4-hydroxy-3-methoxyphenyl)allyl 3-(4-hydroxy-3-methoxyphenyl)acrylate 
• 10570-85-1 ortho-vinylquionone methide 
• 94930-69-5 Acetic acid 2-methoxy-4-(1-methoxy-allyl)-phenyl ester 

Downstream Products

• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 121-33-5 vanillin 
• 20649-42-7 coniferaldehyde 

Relevant articles and documents

Chemodivergent hydrogenolysis of eucalyptus lignin with Ni@ZIF-8 catalyst

Reductive catalytic fractionation (RCF) of lignocellulosic biomass, that is depolymerization of the native lignin component into well-defined monomeric phenols in the first step, offers an opportunity to utilize entire biomass components. Herein, we report that Ni@ZIF-8 can serve as a chemodivergent catalyst in RCF of eucalyptus sawdust, thus selectively producing phenolic compounds having either a propyl or propanol end-chain under different reaction conditions. In both cases, high yields of lignin monomers and a high degree of delignification were achieved, next to well-preserved carbohydrate pulp suitable for further processing. A mechanistic study using model compounds indicated that the dehydroxylation at the γ-position of the β-O-4 structure may be involved in the selectivity-controlling step.

Oxidative Studies on trans-(3-Phenyl-2-propenyl)phenols and 2-Methoxy-4-(2-propenyl)phenol and 2-Methoxy-4-(1-propenyl)phenol

Oxidative reaction on trans-2-(3-phenyl-2-propenyl)phenols (1-4) and para-alkenylphenols have been studied.The products formed include benzofurane (5-8) and neolignane (16-18).

Synthesis and Reactivity of Vinyl Quinone Methides

Vinyl quinone methides 4a and 4b were obtained in high yields by Ag2O oxidation of eugenol (3a) and of 2,6-dimethoxy-4-(2-propenyl)phenol (3b).Vinyl quinone methides (VQMs) reacted with alcohols, with phenols, and with acetic acid giving compounds 5 and 6.As the former rearranged to the latter in the reaction medium, the addition of the reported substrates to VQMs turned out to be wholly regioselective toward the formation of coniferyl and sinapyl derivatives 6.In contrast, addition of carbon nucleophiles (acetylacetone and EtNO2) to VQMs gave both compounds 7 and 8.By reaction of the acetates 6a and 6b (CR=CH3CO) with LiAlH4 it was possible to perform a novel synthesis of coniferyl and sinapyl alcohols (1a and 1b).Treatment of the same acetates with an aqueous solution of NaHCO3 reproduced VQMs 4, which by subsequent reduction with NaBH4, gave propenylphenols 2 and allylphenols 3.Formation of the latter compounds from coniferyl and sinapyl acetates via VQM is here proposed as a possible biosynthetic pathway.