6380-29-6

Upstream product

• 89-83-8 thymol 
• 98-88-4 benzoyl chloride 
• 28178-94-1 4-hydroxy-5-isopropyl-2-methyl-benzophenone 
• 65-85-0 benzoic acid 

Downstream Products

• 15062-34-7 4-bromo-2-isopropyl-5-methylphenol 
• 28178-94-1 4-hydroxy-5-isopropyl-2-methyl-benzophenone 
• 89-83-8 thymol 
• 2782-40-3 N-butylbenzamide 
• 26821-99-8 4-bromo-2-isopropyl-1-methoxy-5-methylbenzene 
• 69065-15-2 2,5-dibromo-p-cumene 

Relevant academic research and scientific papers

Thymol and eugenol derivatives as potential antileishmanial agents

In Northeastern Brazil visceral leishmaniasis is endemic with lethal cases among humans and dogs. Treatment is toxic and 5-10% of humans die despite treatment. The aim of this work was to survey natural active compounds to find new molecules with high activity and low toxicity against Leishmania infantum chagasi. The compounds thymol and eugenol were chosen to be starting compounds to synthesize acetyl and benzoyl derivatives and to test their antileishmanial activity in vitro and in vivo against L. i. chagasi. A screening assay using luciferase-expressing promastigotes was used to measure the growth inhibition of promastigotes, and an ELISA in situ was performed to evaluate the growth inhibition of amastigote. For the in vivo assay, thymol and eugenol derivatives were given IP to BALB/c mice at 100 mg/kg/day for 30 days. The thymol derivatives demonstrated the greater activity than the eugenol derivatives, and benzoyl-thymol was the best inhibitor (8.67 ± 0.28 μg/mL). All compounds demonstrated similar activity against amastigotes, and acetyl-thymol was more active than thymol and the positive control drug amphotericin B. Immunohistochemistry demonstrated the presence of Leishmania amastigote only in the spleen but not the liver of mice treated with acetyl-thymol. Thus, these synthesized derivatives demonstrated anti-leishmanial activity both in vitro and in vivo. These may constitute useful compounds to generate new agents for treatment of leishmaniasis.

Mechanically induced solvent-free esterification method at room temperature

Herein, we describe two novel strategies for the synthesis of esters, as achieved under high-speed ball-milling (HSBM) conditions at room temperature. In the presence of I2 and KH2PO2, the reactions afford the desired esterification derivatives in 45% to 91% yields within 20 min of grinding. Meanwhile, using KI and P(OEt)3, esterification products can be obtained in 24% to 85% yields after 60 min of grinding. In addition, the I2/KH2PO2 protocol was successfully extended to the late-stage diversification of natural products showing the robustness of this useful approach. Further application of this method in the synthesis of inositol nicotinate was also discussed. This journal is

Tropolonate salts as acyl-transfer catalysts under thermal and photochemical conditions: Reaction scope and mechanistic insights

Acyl-transfer catalysis is a frequently used tool to promote the formation of carboxylic acid derivatives, which are important synthetic precursors and target compounds in organic synthesis. However, there have been only a few structural motifs known to efficiently catalyze the acyl-transfer reaction. Herein, we introduce a different acyl-transfer catalytic paradigm based on the tropolone framework. We show that tropolonate salts, due to their strong nucleophilicity and photochemical activity, can promote the coupling reaction between alcohols and carboxylic acid anhydrides or chlorides to give products under thermal or blue light photochemical conditions. Kinetic studies and density functional theory calculations suggest interesting mechanistic insights for reactions promoted by this acyl-transfer catalytic system.

Synthesis, antimicrobial activity and in silico studies on thymol esters

Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.

Solid-Phase Benzoylation of Phenols and Alcohols in Microwave Reactor: An Ecofriendly Protocol

An efficient solid-phase benzoylation of phenols and alcohols was developed under microwave irradiation. A stoichiometric amount of benzoyl chloride was sufficient to carry out the reaction. This benzoylation features short reaction time, good yields, and easy workup procedures. Furthermore, the scope of the reaction was extended to prepare 3,5-dinitrobenzoyl derivatives of alcohols.

Synthesis and in vitro antibacterial activity of thymol and carvacrol derivatives

Fourteen esters of thymol and carvacrol were synthesized and characterized on the basis of spectral data. The NMR data for some of these are being given for the first time. The antibacterial activity screening of thymol, carvacrol and their esters were carried out against four Gram-positive (Streptococcus mutans MTCC 890, Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121, Staphylococcus epidermidis MTCC 435) and one Gram-negative (Escherichia coli MTCC 723) bacteria. The enhancement in activity was noticed in the thymyl ester derivatives 4a-c (against S. mutans, B. subtilis and S. epidermidis) in comparison to thymol, whereas the carvacrol derivatives were found to be much less active than carvacrol.

Antinociceptive effect of extracts and compounds from Hofmeisteria schaffneri

Ethnopharmacological relevance: Hofmeisteria schaffneri (Asteraceae) is a medicinal plant widely commercialized in the most important Markets of Mexico City for the treatment of gastro-intestinal complaints and skin afflictions. Aim of the study: The main goals of this study were to establish the potential acute toxicity and the antinociceptive activity in animal models of several preparations and compounds from Hofmeisteria schaffneri. Materials and methods: The aqueous and organic extracts as well as the essential oil of Hofmeisteria schaffneri were prepared by infusion, maceration and hydrodistillation, respectively. Investigation of the acute toxicity was accomplished by the Lorke method. The antinociceptive effect was assessed using the writhing and the hot plate tests. Natural compounds were isolated by standard phytochemical procedures. In addition, a few thymol esters were prepared by chemical synthesis. The stability of natural and synthetic esters was qualitatively analyzed by measuring their susceptibility to hydrolysis by pig liver estearase and mouse plasma at 37°C. Results: The LD50 for each preparation tested was higher than 5000mg/kg revealing that they were not toxic to mice after exposure for short space of time. On the other hand, the extracts showed significant antinociceptive effect when tested in the hot plate model. The most active natural product as antinociceptive agent was hofmeisterin III (1) which also was the most stable in the stability study. Its pharmacological effect seems to be partially mediated by an opioid mechanism since naloxone inhibits its action. Using compound 1 as a lead molecule, several synthetic thymol esters were prepared and only compounds 13, 15 and 17 were antinoceptive at the dose of 1mg/kg. Conclusions: The present investigation provided evidence of the efficacy of several preparations of Hofmeisteria schaffneri as antinociceptive agents. The most active preparation was the essential oil which contained large amount of hofmeisterin III (1) and other thymol derivatives. Some novel synthetic analogs of hofmeisterin III with antinociceptive properties were discovered. The nature of the ester chain of these analogs did not have a clear impact on the antinociceptive activity. The phyto-preparations analyzed in this study were not toxic to mice according to the Lorke's test; therefore considering their long term use of the plant they might be secure for human consumption.

Commercial zinc oxide (Zn2+) as an efficient and environmentally benign catalyst for homogeneous benzoylation of hydroxyl functional groups

The solvent-free O-acylation of some alcohols with benzoyl chloride was carried out to the corresponding benzoylated products in good to excellent yields by the mediation of a catalytic amount (5 mol%) of the commercially available and inexpensive zinc oxide in short reaction times. This methodology represents an eco-friendly and simple catalytic alternative for benzoylation of primary, secondary, tertiary, and benzylic alcohols with ZnO. This catalytic system was homogeneous because of high solubility of zinc oxide in the reaction medium. Findings showed that ZnO was dissolved in hydrochloric acid, created in situ, after a few minutes. Although, others argued on the catalytic role of solid phase zinc oxide under a heterogeneous condition, it is not surprising to emphasize on the catalytic function of Zn2+ in the benzoylation of alcohols under homogeneous reaction conditions. Zinc oxide served as pre-catalyst to form Zn2+, as the catalytically active species.

Microwave-assisted sinthesis of thymyl ethers and esters in aqueous medium

Various thymyl ethers and esters have been synthesized by reactions of thymol with alkyl halides and acid chlorides, respectively, in aqueous medium under environmentally benign conditions using microwave irradiation. The products are important as potent pest managing agents.