7504-66-7

Usage

InChI:InChI=1/C13H16O3/c1-4-6-10-7-8-11(12(9-10)15-3)16-13(14)5-2/h4,7-9H,1,5-6H2,2-3H3

Upstream product

• 97-53-0 4-allylguaiacol 
• 123-62-6 propionic acid anhydride 
• 79-03-8 propionyl chloride 

Downstream Products

• 92666-22-3 (E)-2-methoxy-4-(1-propen-1-yl)phenyl propionate 

Relevant academic research and scientific papers

Synthesis of eugenol derivatives and its anti-inflammatory activity against skin inflammation

Eugenol is a phytochemical present in aromatic plants has generated considerable interest in the pharmaceutical industries mainly in cosmetics. A series of eugenol esters (ST1-ST7) and chloro eugenol (ST8) have been synthesized. The structures of newly synthesized compounds were confirmed by 1H and 13C NMR and mass spectrometry. In an effort to evaluate the pharmacological activity of eugenol derivatives, we explored its anti-inflammatory potential against skin inflammation using in-vitro and in-vivo bioassay. Synthesized derivatives significantly inhibited the production of pro-inflammatory cytokines against LPS-induced inflammation in macrophages. Among all derivatives, ST8 [Chloroeugenol (6-chloro, 2-methoxy-4-(prop-2-en-1-yl)-phenol)] exhibited most potent anti-inflammatory activity without any cytotoxic effect. We have further evaluated the efficacy and safety in in-vivo condition. ST8 exhibited significant anti-inflammatory activity against TPA-induced skin inflammation without any skin irritation effect on experimental animals. These findings suggested that ST8 may be a useful therapeutic candidate for the treatment of skin inflammation.

Eugenol ester analogue and preparation method thereof as well as insecticide

The invention relates to a eugenol ester analogue and application thereof and in particular relates to the eugenol ester analogue and a preparation method thereof as well as insecticide. The preparation method of the eugenol ester analogue comprises the following steps: (1) carrying out acylating chlorination on substituted carboxylic acid to obtain an intermediate product; (2) enabling the intermediate product and eugenol to react under the condition that an acid binding agent and an organic solvent exist, so as to obtain the eugenol ester analogue, wherein a substituent group in the substituted carboxylic acid is selected from one of C1 to C10 alkyl, C1 to C10 alkenyl, aryl, furyl and imidazolyl. The eugenol ester analogue prepared by the method provided by the invention has a remarkablelethal effect on agricultural insect pests and the insect pests also can have an octopamine agonist poisoning symptom; the eugenol ester analogue can be used as the insecticide and is widely appliedto agriculture.

Synthesis, antimicrobial activity and in silico studies on eugenol eters

The results presented herein represent our continued study based on the modification of phenolic functionality in molecules originated from natural sources by acylation. A small focused library of nineteen eugenyl esters, with four of which are new compounds, is reported. All compounds were subjected to in vitro antimicrobial testing. In silico studies were carried out calculating physico-chemical, pharmacokinetic and toxicological properties, providing more data as additional guidance for further research.

Synthesis and antibacterial study of eugenol derivatives

A series of eugenol derivatives (2-14) were synthesized and evaluated for their antibacterial activity against five bacterial test strains; three Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus and Staphylococcus epidermidis) and two Gram-negative bacteria (Escherichia coli and Salmonella typhimurium) using well-diffusion method. Among the compounds tested, compounds 2-4 displayed susceptible activity toward S. epidermidis with 16-18 mm whereas compounds 12 exhibited susceptible inhibition towards S. aureus only with inhibition diameter of 16 mm, respectively. Other compounds possessed varied antibacterial activities classified as intermediate or resistance indicating that eugenol derivatives have narrow spectrum activity and specifically to Gram-positive bacteria.

Eugenol fatty acid ester derivative as well as application and preparation method thereof

The invention discloses a eugenol fatty acid ester derivative as well as application and a preparation method thereof. Eugenol fatty acid ester is obtained by an esterification reaction of eugenol and straight-chain fatty acid. The method comprises the following steps: firstly, preparing acyl chlorine by reacting fatty acid with thionyl chloride; mixing eugenol with an equal mole amount of pyridine or triethylamine; then, dropwise adding the prepared acyl chloride under the cooling action of an ice bath to generate the eugenol fatty acid ester. Eugenol ester can be applied to external preparations such as patches, cataplasm, ointments, gels and spray agents as a penetration enhancer in order to increase the transdermal absorption amount of medicaments, is a very good percutaneous absorption penetration enhancer, and has a wide application prospect.

Eugenol derived immunomodulatory molecules against visceral leishmaniasis

Visceral leishmaniasis (VL) is a life threatening infectious disease caused by Leishmania donovani. It leads to the severe immune suppression in the host defense system. Higher cytotoxicity, rigorous side effects and lower therapeutic indexes (TI) of current antileishmanial drugs have created a necessity to develop new molecules with better antileishmanial activity and high TI value. In this study, we have synthesized 36 derivatives of eugenol and screened them for their activity against promastigote and amastigote forms of L. donovani. Among the synthesized derivatives, comp.35 showed better antileishmanial activity against extra cellular promastigotes (IC50- 20.13 ± 0.91 μM) and intracellular amastigotes (EC50-4.25 ± 0.26 μM). The TI value (82.24 ± 3.77) was found to improve by 10–13 fold compared to Amphotericin B and Miltefosine respectively. Treatment with comp.35 (5 μg/ml) enhanced the nitric oxide (NO) generation, iNOS2 mRNA expression (～8 folds increase) and decreased the arginase-1 activity (～4 folds) in L. donovani infected peritoneal macrophages. Comp.35 had also increased the IL-12 (～6 folds) and decreased the IL-10 (～3 folds) mRNA expression and release in vitro. Results of in vivo studies revealed that comp.35 treatment at 25 mg/kg body weight efficiently cleared the hepatic and splenic parasite burden with enhanced Th1 response in L. donovani infected BALB/c mice. Hence, this study clearly represents comp.35, as an immunomodulatory molecule, can induce host protective immune response against visceral leishmaniasis through enhanced NO generation and Th1 response, which are essentials against this deadly disease.

A general route for the stereoselective synthesis of (E)-(1-propenyl)phenyl esters by catalytic CC bond isomerization

A general and efficient procedure for the stereoselective synthesis of (E)-(1-propenyl)phenyl esters from readily accessible allylphenols has been developed. The process involves a two-step sequence consisting of the initial acylation of the allylphenols with an acid chloride, followed by catalytic CC bond isomerization in the resulting allylphenyl esters. The latter step was performed in methanol at 80 °C using catalytic amounts (0.5 mol %) of the commercially available bis(allyl)-ruthenium(IV) dimer [{RuCl(μ-Cl) (η3:η3-C10H16)} 2] (C10H16=2,7-dimethylocta-2,6-diene-1,8-diyl) . Reactions proceeded in high yields (68-93%) and short times (4-9 h) with complete E-selectivity.