3934-89-2

Usage

Type of compound

Natural phenolic compound

Plant sources

Found in a variety of plant sources, including the root extract of Smilax china

Antioxidant

Capable of neutralizing harmful free radicals

Anti-inflammatory

Helps reduce inflammation in the body

Neuroprotective

Protects neurons from damage, potentially useful in treating neurodegenerative diseases

Phenolic ring

Contains two hydroxyl groups and a methoxy group

Ketone functional group

A carbonyl group (C=O) bonded to an alkyl group

Key intermediate

Used in the synthesis of natural products and pharmaceutical compounds

Potential therapeutic use

May be useful in the treatment of neurodegenerative diseases and other health conditions

Upstream product

• 103440-59-1 1-(4-hydroxy-3-iodo-5-methoxy-phenyl)ethan-1-one 
• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 

Downstream Products

• 2478-38-8 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone 

Relevant academic research and scientific papers

Enhancing the Antioxidant Activity of Technical Lignins by Combining Solvent Fractionation and Ionic-Liquid Treatment

A grass soda technical lignin (PB1000) underwent a process combining solvent fractionation and treatment with an ionic liquid (IL), and a comprehensive investigation of the structural modifications was performed by using high-performance size-exclusion ch

Detection of an O-methyltransferase synthesising acetosyringone in methyl jasmonate-treated tobacco cell-suspensions cultures

Acetosyringone (3′,5′-dimethoxy-4′-hydroxyacetophenone) is a well-known and very effective inducer of the virulence genes of Agrobacterium tumefaciens but the precise pathway of its biosynthesis in plants is still unknown. We have used two tobacco cell lines, cultured in suspension and exhibiting different patterns of accumulation of acetosyringone in their culture medium upon treatment with methyl jasmonate, to study different steps of acetosyringone biosynthesis. In the two cell lines studied, treatment with 100 μM methyl jasmonate triggered a rapid and transient increase in acetovanillone synthase activity followed by a progressive increase in S-adenosyl-L-methionine: 5-hydroxyacetovanillone 5-O-methyltransferase activity which paralleled the rise in acetosyringone concentration in the culture medium. This O-methyltransferase displayed Michaelis-Menten kinetics with an apparent Km value of 18 μM for 5-hydroxyacetovanillone and its activity was magnesium-independent. Its molecular mass was estimated by gel permeation on an FPLC column and was found to be of ca. 81 kDa. 5-Hydroxyacetovanillone was the best substrate among the different o-diphenolic compounds tested as methyl acceptors in the O-methyltransferase assay. No formation of 5- hydroxyacetovanillone could be detected in vitro from 5-hydroxyferuloyl-CoA and NAD in the extracts used to measure acetovanillone synthase activity, indicating that 5-hydroxyacetovanillone is probably formed by direct hydroxylation of acetovanillone rather than by β-oxidation of 5-hydroxyferulic acid. Taken together our results strongly support the hypothesis that acetosyringone biosynthesis in tobacco proceeds from feruloyl-CoA via acetovanillone and 5-hydroxyacetovanillone.