4732-13-2

Usage

Chemical Properties

Carvacryl ethyl ether has a warm spicy herbaceous aroma, similar to carrot.

Preparation

By passing vapors of ethyl alcohol and carvacrol over a catalyst (ThO2) at 400 to 500°C.

InChI:InChI=1/C12H18O/c1-5-13-12-8-11(9(2)3)7-6-10(12)4/h6-9H,5H2,1-4H3

Upstream product

• 64-17-5 ethanol 
• 499-75-2 carvacrol 
• 2437-76-5 2-bromo-p-cymene 
• 141-52-6 sodium ethanolate 
• 75-03-6 ethyl iodide 
• 64-67-5 diethyl sulfate 
• 74-96-4 ethyl bromide 

Downstream Products

• 576-55-6 tetrabromo-o-cresol 
• 74295-30-0 ethoxy-terephthalic acid 

Relevant academic research and scientific papers

Synthesis and biological evaluation of carvacrol-based derivatives as dual inhibitors of H. Pylori strains and ags cell proliferation

This study reports on the synthesis, structural assessment, microbiological screening against several strains of H. pylori and antiproliferative activity against human gastric adenocarcinoma (AGS) cells of a large series of carvacrol-based compounds. Structural analyses consisted of elemental analysis,1 H/13 C/19 F NMR spectra and crystallographic studies. The structure-activity relationships evidenced that among ether derivatives the substitution with specific electron-withdrawing groups (CF3 and NO2) especially in the para position of the benzyl ring led to an improvement of the antimicrobial activity, whereas electron-donating groups on the benzyl ring and ethereal alkyl chains were not tolerated with respect to the parent compound (MIC/MBC = 64/64 μg/mL). Ester derivatives (coumarin-carvacrol hybrids) displayed a slight enhancement of the inhibitory activity up to MIC values of 8–16 μg/mL. The most interesting compounds exhibiting the lowest MIC/MBC activity against H. pylori (among others, compounds 16 and 39 endowed with MIC/MBC values ranging between 2/2 to 32/32 μg/mL against all the evaluated strains) were also assayed for their ability to reduce AGS cell growth with respect to 5-Fluorouracil. Some derivatives can be regarded as new lead compounds able to reduce H. pylori growth and to counteract the proliferation of AGS cells, both contributing to the occurrence of gastric cancer.

Synthesis and tyrosinase inhibitory activities of 4-oxobutanoate derivatives of carvacrol and thymol

Carvacrol (1) and thymol (2) were converted to their alkyl 4-oxobutanoate derivatives (7–20) in three steps, and evaluated for tyrosinase inhibitory activity. The compounds showed structure-dependent activity, with all alkyl 4-oxobutanoates, except 7 and 20, showing better inhibitory activity than the precursor 4-oxobutanoic acids (5 and 6). In general, thymol derivatives exhibited a higher percent inhibitory activity than carvacrol derivatives at 500 μM. Derivatives containing three-carbon and four-carbon alkyl groups gave the strongest activity (carvacrol derivatives 9–12, IC50 = 128.8–244.1 μM; thymol derivatives 16–19, IC50 = 102.3–191.4 μM).

Phenylimidazole derivative, synthesis method of phenylimidazole derivative and application of phenylimidazole derivative to pesticide

The invention relates to a phenylimidazole derivative, a synthesis method of the phenylimidazole derivative and application of the phenylimidazole derivative to pesticide, particularly application tothe fungicide pesticide aspect, and belongs to the technical field of pesticide. In order to solve the technical problems, the invention provides a novel phenylimidazole derivative, a synthesis methodof the novel phenylimidazole derivative and application of the novel phenylimidazole derivative to the pesticide. The structure of the compound is shown as a formula I. The compound structure is simple and novel; the synthesis is easy; meanwhile, the fungicidal activity is realized; a better bacteriostasis or sterilization effect is achieved on important plant pathogenic fungi such as tomato early blight, tomato botrytis cinereal, cucumber fusarium oxysporum, magnaporthe grisea and rice rhizoctonia solani.

Antifungal activity of phenolic monoterpenes and structure-related compounds against plant pathogenic fungi

The aim of this work is to explore the possibility of using the phenolic monoterpenes (PMs) as leading compounds with antifungal activity against plant disease. The in vitro antifungal activities of carvacrol and thymol against seven kinds of plant pathogenic fungi were evaluated on mycelium growth rate method, and the results showed that carvacrol and thymol exhibited broad spectrum antifungal activity. Structure requirement for the antifungal activity of PMs was also investigated. The preliminary conclusion was that phenolic hydroxyl and monoterpene were basic structures for the antifungal activity of PMs, and the position of phenolic hydroxyl showed less effect. Ester derivatives of carvacrol and thymol were more effective than carvacrol and thymol against plant pathogenic fungi. We suggested that carvacrol, thymol and their ester derivatives could potentially be used as new fungicide leading compounds.

Solid-supported synthesis of bio-active carvacrol compounds using microwaves

The most abundant and potent natural products having a broad spectrum of biological activity against various pests are terpenoids, especially monoterpenoids. The chemical modification of natural monoterpenoids has been reported to result in modified biological activity. The present work emphasizes the structural modification of carvacrol, a phenolic monoterpenoid, through the synthesis of different ether and ester derivatives that are useful for structure-activity relationship studies to exploit the potent molecules. The carvacrol was reacted with alkyl halides and acid chlorides under microwaves using solid supports such as silica gel, alumina, and fly ash to give ethers and esters, respectively. The synthesis of dimeric ether and ester compounds using dihalides and acid dichlorides was conducted with novel reactions. Additional features of the methodology include very fast reactions, higher yields and purities of the products, and an ecofriendly approach. Copyright Taylor & Francis Group, LLC.

Synthesis of biologically active carvacrol compounds using different solvents and supports

Natural monoterpenoids have been documented for their acute toxicity and repellent, antifeedent, reproduction inhibitory, and insecticidal actions. The present work aims to derive a variety of ether and ester compounds using polymer-supported reactions from the polymer-supported carvacrol anion was reacted with alkyl halides and acid chlorides to afford carvacryl ethers and esters, respectively. Furthermore, a special study on the effect of different solvents and supports revealed that Amberlite IRA 400 (chloride form) was found to be the best polymer support and acetone among the solvents. Copyright Taylor & Francis Group, LLC.