118709-62-9

Basic information

• Product Name: (3E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one
• Synonyms: (3E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one
• CAS NO: 118709-62-9
• Molecular Weight: 236.268
• Mol File: 118709-62-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (3E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one(118709-62-9)
• EPA Substance Registry System: (3E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one(118709-62-9)

Safety Data

• Hazardous Substances Data: 118709-62-9(Hazardous Substances Data)

Usage

Description

(3E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one is a phenylpropanoid compound derived from phenylalanine, which is a natural product with a yellowish liquid appearance and a strong, sweet, floral odor. It has been isolated from various plant sources and exhibits antioxidant, anti-inflammatory, and potential anticancer properties.

Uses

Used in Cosmetic Industry:
(3E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one is used as a fragrance ingredient for its strong, sweet, floral odor, contributing to the creation of pleasant scents in cosmetic products.
Used in Food Industry:
(3E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one is used as a flavoring agent to enhance the taste and aroma of food products, providing a sweet and floral note.
Used in Pharmaceutical Applications:
(3E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one is being investigated for its potential use as a pharmaceutical agent due to its antioxidant, anti-inflammatory, and anticancer properties, which may contribute to the development of new treatments for various health conditions.

Upstream product

• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 67-64-1 acetone 

Downstream Products

• 1450740-28-9 5-methyl-5-[(E)-2-(2,3,4-trimethoxyphenyl)ethenyl]-2,5-dihydrofuran-2-one 
• 1450740-54-1 ethyl (5E)-4-hydroxy-4-methyl-6-(2,3,4-trimethoxyphenyl)hex-5-en-2-ynoate 
• 1217503-49-5 (1E,4E)-1-(2,3,4-trimethoxyphenyl)-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one 
• 119101-29-0 2,3,3',4-tetramethoxy-5'-<(1-phenyl-1H-5-tetrazolyl)oxy>-1,1'-biphenyl 
• 119101-25-6 3-methoxy-5-(2,3,4-trimethoxyphenyl)-2-cyclohexen-1-one 

Relevant articles and documents

Organoselenium-catalyzed baeyer-villiger oxidation of α,β-unsaturated ketones by hydrogen peroxide to access vinyl esters

By carefully screening the organoselenium pre-catalysts and optimizing the reaction conditions, simple dibenzyl diselenide was found to be the best pre-catalyst for Baeyer-Villiger oxidation of (E)-α,β-unsaturated ketones with the green oxidant hydrogen peroxide at room temperature. The organoselenium catalyst used in this reaction could be recycled and reused several times. This new method was suitable not only for methyl unsaturated ketones, but also for alkyl and aryl unsaturated ketones. Therefore, it provided a direct, mild, practical, highly functional group-tolerant process for the chemoselective preparation of the versatile (E)-vinyl esters from the readily available (E)-α,β-unsaturated ketones. A possible mechanism was also proposed to rationalize the activity of the organoselenium catalyst in the presence of hydrogen peroxide in this Baeyer-Villiger oxidation reaction.

Design, synthesis and in vitro evaluation against human cancer cells of 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, a new series of goniothalamin analogues

The present work describes the preparation of a novel series of compounds based on the structure of goniothalamin (1), a natural styryl lactone with known cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 17 goniothalamin analogues displaying the 5-methyl-2,5-dihydrofuran-2-one motif were prepared, and their cytotoxicity evaluated. While the analogues bearing methoxy and/or hydroxy groups on the aromatic moiety usually were at least three times less potent than the lead compound (1), ortho and para-trifluoromethyl analogues 10 and 11 exhibited levels of cytotoxicity similar to goniothalamin (1) against most cancer cell lines evaluated. One could suggest that the electronic effect of the trifluoromethyl group activates the inhibitor's electrophilic site via reduction of the electron density of the α,β-unsaturated ester oxygen atom. These results provide new information on the structure activity relationship of these α,β-unsaturated styryl lactones, thereby further focusing the design of novel candidates.

Styryl ketones

Styryl ketones of the formula STR1 wherein R8 and R9 are independently hydrogen or lower alkyl or together represent an additional carbon-carbon bond and R10 is a group of the formula STR2 as well as corresponding compounds of the formula STR3 wherein R10' is a group of formula (a), (b), (d) or (e) or a group of the formula have mucosa-protective and/or gastric acid secretion-inhibiting properties, such that they can be used for the control or prevention of illnesses of the gastrointestinal tract, especially against gastric ulcers or duodenal ulcers.