36014-34-3

Usage

Type of compound

Epoxide (contains a three-membered ring with one oxygen atom and two carbon atoms)

Uses

Production of surface coatings, adhesives, and sealants; building block in the synthesis of pharmaceuticals and agrochemicals

Potential medical applications

Studied for treatment of certain medical conditions

Safety precautions

Can be toxic if ingested or inhaled; can cause skin and eye irritation

Upstream product

• 97-53-0 4-allylguaiacol 
• 106-89-8 epichlorohydrin 

Downstream Products

• 398-58-3 3-(4-allyl-2-methoxyphenoxy)-1,2-propanediol 
• 20041-39-8 eugenol 
• 79036-70-7 2-((4-(2-hydroxypropyl)-2-methoxyphenoxy)methyl)-15-crown-5 
• 84130-98-3 2-((2-methoxy-4-propylphenoxy)methyl)-15-crown-5 
• 84130-99-4 2-((4-allyl-2-methoxyphenoxy)methyl)-15-crown-5 

Relevant academic research and scientific papers

Synthesis, activity, and molecular modeling studies of 1,2,3-triazole derivatives from natural phenylpropanoids as new trypanocidal agents

The search for compounds with new structural scaffolds is an important tool to the discovery of new drugs against Chagas disease. We report herein the synthesis of 1,2,3-triazoles obtained from eugenol and di-hydroeugenol and their in vitro and in vivo tr

Novel eugenol bearing oxypropanolamines: Synthesis, characterization, antibacterial, antidiabetic, and anticholinergic potentials

Five oxypropanol amine derivatives that four of them are novel have been synthesized with high yields and practical methods. in vitro antibacterial susceptibility of Acinetobacter baumannii, Pseudomonas aeruginosa, Escherichia coli and Staphylococcus aure

Bio-based polyesters synthesized by ring-opening copolymerizations of eugenyl glycidyl ether and cyclic anhydrides using a binuclear [OSSO]CrCl complex

A novel binuclear chromium complex of dianionic [OSSO]-type ligand has been synthesized and employed toward the ring-opening copolymerization of renewable eugenyl glycidyl ether (EGE) and cyclic anhydrides (CAs) (succinic anhydride (SA), phthalic anhydrid

Synthesis of Bio-Based Silane Coupling Agents by the Modification of Eugenol

A simple method for the synthesis of new bio-based silane coupling agents (SCAs) with a terpene aromatic core by the functionalization of cheap, natural eugenol and its sulfur derivatives using the hydrosilylation of the C=C bonds with HSi(OEt)3/sub

Organosilicon-modified eugenol-based epoxy diluent Preparation method and application thereof

The invention discloses an organosilicon-modified eugenol-based epoxy diluent and a preparation method and application thereof. The eugenol glycidyl ether is prepared by mixing eugenol and epoxy chloropropane under the action of a quaternary ammonium salt

Design, synthesis, and in silico studies of novel eugenyloxy propanol azole derivatives having potent antinociceptive activity and evaluation of their β-adrenoceptor blocking property

The design, synthesis, antinociceptive and β-adrenoceptor blocking activities of several eugenyloxy propanol azole derivatives have been described. In this synthesis, the reaction of eugenol with epichlorohydrin provided adducts 3 and 4 which were N-alkylated by diverse azoles to obtain the eugenyloxy propanol azole analogues in good yields. Adducts 3 and 4 were also reacted with azide ion to obtain the corresponding azide 6. The ‘Click’ Huisgen cycloaddition reaction of 6 with diverse alkynes afforded the title compounds in good yields. The synthesized eugenyloxy propanol azole derivatives were in vivo studied for the acute antinociception on male Spargue Dawley rats using tail-flick test. Compounds 5f, 5g, 7b and 11a exhibited potent analgesic properties in comparison with eugenol as a standard drug. In addition, all compounds were ex vivo tested for β-adrenoceptor blocking properties on isolated left atrium of male rats which exhibited partial antagonist or agonist behaviour compared to the standard drugs. The molecular docking study on the binding site of transient receptor potential vanilloid subtype 1 (TRPV1) has indicated that like capsaicin, eugenyloxy propanol azole analogues exhibited the strong affinity to bind at site of TPRV1 in a “tail-up, head-down” conformation and the presence of triazolyl moieties has played undeniable role in durable binding of these ligands to TRPV1. The in silico pharmacokinetic profile, drug likeness and toxicity predictions carried out for all compounds determined that 5g can be considered as potential antinociceptive drug candidate for future research.

Eugenol-based epoxy resin and preparation process and application thereof

The invention discloses a preparation process of eugenol-based epoxy resin. The preparation process comprises the steps that (1) eugenol, epichlorohydrin and a catalyst A are added under the normal pressure, etherification ring-opening reaction is conduct

Alternating and regioregular copolymers with high refractive index from COS and biomass-derived epoxides

This study describes the catalytic formation of alternating and regioregular copolymers from carbonyl sulfide (COS) and epoxides along with eugenol-based glycidyl ether (EGE) and guaiacol-based glycidyl ether (GGE), derived from eugenol and guaiacol, respectively. The (salen)CrCl [salen = N,N′-bis(salicylidene) cyclohexanediimine] complex, accompanied with various organic bases, was highly active towards the EGE/COS, GGE/COS copolymerization and EGE/GGE/COS terpolymerization. The turnover of frequency (TOF) of the (salen)CrCl complex for the EGE/COS copolymerization was up to 12000 h-1. The number-average molecular weight (Mn) of the resultant EGE/COS copolymer was up to 62.2 kg mol-1. In the presence of 0.5-1.5 mol% chlorohydrin, which was a by-product of the synthetic process of EGE, α-Cl, ω-OH EGE/COS copolymers were obtained. This result suggests that chlorohydrin could act as a very efficient chain transfer agent for the copolymerization. The EGE/COS, GGE/COS, and EGE/GGE/COS copolymers were soluble in most of the common solvents and exhibited a high refractive index of more than 1.58 with high Abbe numbers of up to 40.4. This study provides an unprecedented and sustainable synthetic route for making soluble sulfur-rich polymers with high optical properties.

Synthesis of bio-based epoxy monomers from natural allyl- and vinyl phenols and the estimation of their affinity to the estrogen receptor α by molecular docking

Diepoxydized diphenyls from eugenol, 4-vinyl guaiacol and 4-vinyl syringol (canolol) were synthesized as sustainable alternatives to the diglycidyl ether of bisphenol A (DGEBA). In the first step, glycidylated derivatives were produced by reaction with epichlorohydrin. Then, the dimerization of these derivatives was performed by cross metathesis (CM) reaction in the presence of the Grubbs II catalyst. From the CM reaction, a set of epoxy phenolic dimers was obtained in good yields with a high diastereoselectivity. Estimation by molecular docking calculations of the affinity of the synthesized products and their hydrolysed structures to the intranuclear estrogen receptor ERα showed that the epoxy forms presented a moderate affinity to the antagonistic conformation of the receptor (six to forty times lower than bisphenol A and in the same order of magnitude as DGEBA) and mostly no binding in the agonist conformation. The hydrolysed forms of the epoxy products, which are expected to be predominant in the human body cells, exhibited a relatively weak affinity to the ERα LBD in its both agonistic and antagonistic conformations.

A new aspect of view in synthesizing new type β-adrenoceptor blockers with ancillary antioxidant activities

A series of vanilloid-type β-adrenoceptor blockers derived from traditional Chinese herbal medicines were synthesized and tested for their antioxidant and adrenoceptor antagonistic activities. They all possessed significant β-adrenoceptor blocking activities under in vitro experiments and radioligand binding assays. In addition, some compounds were further examined in in vito tests and produced antagonist effects matching that of propranolol and labetalol by measurements of antagonism toward (-)isoproterenol-induced tachycardia and (-)phenylephrine-induced pressor responses in anesthetized rats. Furthermore, all of the compounds had antioxidant effects inherited from their original structures. In conclusion, compound 11 had the most potent β-adrenoceptors blocking activity, 12 and 13 possessed high cardioselectivity, whereas 14, 15 and 16 possessed additional α-adrenoceptor blocking activity and 15 is the most effective antioxidant of all. the antioxidant activity may be due to their @α and β unsaturated side chain at position 1 and ortho-substituted methoxy moiety on 4-phenoxyethylamine. Copyright