59953-93-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(E)-3-(4-(allyloxy)phenyl)acrylic acid is utilized as an intermediate in the synthesis of pharmaceuticals, given its unique chemical structure and reactivity. It plays a crucial role in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, (E)-3-(4-(allyloxy)phenyl)acrylic acid is employed as a building block for the creation of various agrochemicals. Its properties make it suitable for the development of compounds that can be used in the agricultural sector to enhance crop protection and yield.
Used in Dye Manufacturing:
(E)-3-(4-(allyloxy)phenyl)acrylic acid is also used in the production of dyes, capitalizing on its chemical structure to create a range of colors for various applications, including textiles, plastics, and printing inks.
Used in Adhesives and Coatings:
Due to its reactivity and ability to form crosslinked networks, (E)-3-(4-(allyloxy)phenyl)acrylic acid is used as a component in the formulation of adhesives and coatings. This enhances the performance characteristics of these products, such as adhesion strength, durability, and resistance to environmental factors.
Used in Polymer Materials:
(E)-3-(4-(allyloxy)phenyl)acrylic acid is also employed in the production of polymer materials, where its unique properties contribute to the development of advanced materials with specific mechanical, thermal, and chemical properties for various applications.
Used in Anticancer Research:
(E)-3-(4-(allyloxy)phenyl)acrylic acid has been studied for its potential biological activities, particularly its antiproliferative and anticancer properties. This research aims to explore the compound's ability to inhibit the growth of cancer cells and its potential use in the development of novel cancer treatments.

Upstream product

• 3943-97-3 methyl 4-hydroxycinnamate 
• 7400-08-0 p-Coumaric Acid 
• 106-95-6 allyl bromide 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 1262000-26-9 3,4,6-tri-O-allyl-1,2-di-O-[p-(O-allyl)coumaroyl]-β-D-glucopyranose 
• 145613-78-1 2-(4-hydroxyphenyl)ethyl 6-O-(E)-p-coumaroyl β-D-glucopyranoside 
• 191541-00-1 4-prop-2-enyloxycinnamoyl chloride 
• 179129-00-1 (E)-3-(4-Allyloxy-phenyl)-acrylic acid 1-allyloxycarbonyl-2-(3,4-bis-allyloxy-phenyl)-ethyl ester 

Relevant academic research and scientific papers

Prenylated trans-cinnamic esters and ethers against clinical fusarium spp.: Repositioning of natural compounds in antimicrobial discovery

Onychomycosis is a common nail infection mainly caused by species belonging to the F. oxysporum, F. solani, and F. fujikuroi species complexes. The aim of this study was to evaluate the in vitro susceptibility of six representative strains of clinically relevant Fusarium spp. toward a set of natural-occurring hydroxycinnamic acids and their derivatives with the purpose to develop naturally occurring products in order to cope with emerging resistance phenomena. By introducing a prenylated chain at one of the hydroxy groups of trans-cinnamic acids 1–3, ten prenylated derivatives (coded 4–13) were preliminarily investigated in solid Fusarium minimal medium (FMM). Minimal inhibitory concentration (MIC) and lethal dose 50 (LD50) values were then determined in liquid FMM for the most active selected antifungal p-coumaric acid 3,3′-dimethyl allyl ester 13, in comparison with the conventional fungicides terbinafine (TRB) and amphotericin B (AmB), through the quantification of the fungal growth. Significant growth inhibition was observed for prenylated derivatives 4–13, evidencing ester 13 as the most active. This compound presented MIC and LD50 values (62–250 μM and 7.8–125 μM, respectively) comparable to those determined for TRB and AmB in the majority of the tested pathogenic strains. The position and size of the prenylated chain and the presence of a free phenol OH group appear crucial for the antifungal activity. This work represents the first report on the activity of prenylated cinnamic esters and ethers against clinical Fusarium spp. and opens new avenues in the development of alternative antifungal compounds based on a drug repositioning strategy.

Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A

A convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me2SnCl2-catalyzed O-6 acylation of unprotected 2-phenylethyl-β-D-glucosides 5a–b with cinnamoyl chlorides 6a–b in excellent yields. Acylation at O-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid glycosides acylated at O-6.

Synthesis of Albicidin Derivatives: Assessing the Role of N-terminal Acylation on the Antibacterial Activity

The peptide antibiotic albicidin, which is synthesized by the plant pathogenic bacterium, Xanthomonas albilineans, represents the most prominent member of a new class of antibacterial gyrase inhibitors. It shows remarkable antibacterial activities against Gram-positive and Gram-negative microorganisms. Its unique structure potentially represents a new lead structure for the development of an antibacterial drug. Here we report the synthesis of 14 albicidin derivatives with structural variations at the N-terminus, primarily investigating the effects of variation of cinnamoyl, phenylpropanoyl, and benzoyl residues. Gyrase inhibition in vitro and determination of minimal inhibitory concentrations were assessed in parallel. Activities in a nanomolar range and the importance of N-acylation were demonstrated.

Bryophyte constituents; 7: New synthesis of (+)-rosmarinic acid and related compounds

Efficient and expeditious syntheses are described for rosmarinic acid (1) and its derivatives 2-4, making extensive use of allyl protective groups for both carboxylic acids and phenolic building blocks. (+)(R)-Rosmarinic acid was obtained by a chemoenzymatic resolution of its phenyl lactic acid precursors.

ANTIHYPERTENSIVE QUINAZOLINE DERIVATIVES

Novel quinazoline compounds and antihypertensive compositions containing said compounds are disclosed; said compounds having the formula: STR1 wherein R 1 is a hydrogen atom or an alkyl group having 1-5 carbon atoms;R 2 is a group of the formula STR2 in which Y is a hydrogen atom, an alkyl group of 1-5 carbon atoms, an alkoxy group of 1-5 carbon atoms, an alkenyloxy group, a methylenedioxy group, a nitro group, a halogen atom, a trifluoromethyl group, an acyloxy group, a hydroxy group, an unsubstituted or substituted amino group or a condensed benzene nucleus and m is an integer of 1-3 inclusive, or a group of the formula STR3 in which X is an oxygen atom, a sulfur atom or a carbon-nitrogen double bond and Z is a hydrogen atom, an alkyl group of 1-5 carbon atoms, an alkoxy group of 1-5 carbon atoms, a nitro group or a halogen atom; and n is an integer of 2-3 inclusive;provided that, when R 2 is the said group STR4 n is 2 and R 1 is a hydrogen atom or, when R 2 is the said group STR5 n is 2 or 3 and R 1 is a hydrogen atom or the said alkyl group and a pharmaceutically acceptable acid addition salt thereof.