579-60-2

Usage

Uses

Used in Flavor and Fragrance Industry:
O-Eugenol is used as a key component in the flavor and fragrance industry for its distinct spicy and floral aroma. It is widely utilized in the formulation of perfumes, colognes, and other scented products to provide a rich and complex scent profile.
Used in Pharmaceutical Industry:
O-Eugenol is used as an active ingredient in the pharmaceutical industry, particularly in the development of analgesics, anti-inflammatory drugs, and local anesthetics. Its ability to interact with biological systems makes it a valuable compound for the treatment of various medical conditions.
Used in Dental Industry:
In the dental industry, O-Eugenol is used as a temporary filling material and a component in endodontic sealers. Its properties allow it to provide a seal and reduce postoperative pain, making it an essential material in dental procedures.
Used in Antimicrobial Applications:
O-Eugenol exhibits antimicrobial properties, making it useful in the development of antibacterial and antifungal agents. It can be employed in the formulation of disinfectants, sanitizers, and preservatives for various applications, including medical, food, and cosmetic industries.
Used in Anticancer Applications:
Similar to the example provided for Gallotannin, O-Eugenol has been shown to possess anticancer properties. It can be used as an anticancer agent, targeting various types of cancer cells and modulating oncological signaling pathways, potentially enhancing the efficacy of conventional chemotherapeutic drugs.
Used in Drug Delivery Systems:
To improve the bioavailability and therapeutic outcomes of O-Eugenol, novel drug delivery systems have been developed. These systems, which may include organic and metallic nanoparticles, aim to enhance the delivery of O-Eugenol to target cells, making it a more effective compound for various applications, including cancer treatment.

InChI:InChI=1/C10H12O2/c1-3-5-8-6-4-7-9(12-2)10(8)11/h3-4,6-7,11H,1,5H2,2H3

Upstream product

• 4125-43-3 O-allyl guaiacol 
• 23343-06-8 2-allyloxy-3-methoxy-benzaldehyde 
• 121-69-7 N,N-dimethyl-aniline 
• 108-88-3 toluene 
• 120-80-9 benzene-1,2-diol 
• 106-95-6 allyl bromide 
• 74-88-4 methyl iodide 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 90-05-1 2-methoxy-phenol 
• 59744-45-5 1-allyl-2-(allyloxy)-3-methoxybenzene 
• 107-05-1 3-chloroprop-1-ene 
• 6342-70-7 3-methoxymethylsalicylate 
• 877-22-5 3-methoxysalicylic acid 
• 96619-88-4 2-(allyloxy)-3-methoxybenzoic acid 

Downstream Products

• 90920-87-9 5-(2-hydroxy-3-methoxy-phenyl)-[1,2]dithiol-3-thione 
• 1076-55-7 (E/Z)-2-(1-Propenyl)-6-methoxyphenol 
• 86153-98-2 2-methoxy-6-propylphenol 
• 2173-78-6 2-Allyl-6-methoxyphenyl acetate 
• 875841-21-7 1-allyl-2-(2-chloro-ethoxy)-3-methoxy-benzene 
• 860686-94-8 1-allyl-2-[2-(2-chloro-ethoxy)-ethoxy]-3-methoxy-benzene 
• 31788-37-1 2-Allyl-6-methoxy-1,4-benzoquinone 
• 88865-19-4 1,4,4a,8a-tetrahydro-5,5,10,10-tetramethoxy-1,7-bis(2-propenyl)-1,4-ethanonaphthalene-6,9(4H)-dione 
• 101041-45-6 7-Methoxy-2-p-tolylsulfanylmethyl-2,3-dihydro-benzofuran 
• 121936-21-8 2,4-diamino-5-(3-allyl-4-hydroxy-5-methoxybenzyl)pyrimidine 
• 127978-20-5 2-Allyl-6-methoxyphenyl N-mesyl-L-phenylalanylate 
• 126861-92-5 Ethyl (6-allyl-2-methoxyphenoxy)acetate 
• 126708-02-9 2-<2-hydroxy-3-(phenylthio)propyl>-6-methoxyphenol 
• 126708-11-0 2-<3-hydroxy-2-(phenylthio)propyl>-6-methoxyphenol 

Relevant academic research and scientific papers

Subsupercritical Water Generated by Inductive Heating Inside Flow Reactors Facilitates the Claisen Rearrangement

Claisen rearrangement of electron-deficient O-allylated phenols, including fluorine-modified phenols, is facilitated in aqueous media at high temperatures and pressures under flow conditions, as opposed to organic solvents. The O-allylation of phenols can be coupled with the Claisen rearrangement in an integrated flow system.

Synthesis and First-Time Assessment of o-Eugenol Derivatives against Mycobacterium tuberculosis

In this work, we report the first-time assessment of o-eugenol, 6-allyl-2-methoxyphenol, and their selected derivatives, against Mycobacterium tuberculosis H37RV, using the MABA susceptibility test. The bromo, nitro, O-alkylated, and reduced derivatives were obtained by standard methods and were characterized by spectroscopic and mass spectral data. Structure–activity relationships were investigated, with the most active derivatives being 4,5-dibromo-2-methoxy-6-propylphenol (139 μM) and 2-methoxy-3-nitro-6-propylphenol (237 μM). This study provides important information on the rational design of new lead anti-TB drugs based on o-eugenol derivatives.

Semisynthetic Phenol Derivatives Obtained from Natural Phenols: Antimicrobial Activity and Molecular Properties

Semisynthetic phenol derivatives were obtained from the natural phenols: thymol, carvacrol, eugenol, and guaiacol through catalytic oxychlorination, Williamson synthesis, and aromatic Claisen rearrangement. The compounds characterization was carried out by 1H NMR, 13C NMR, and mass spectrometry. The natural phenols and their semisynthetic derivatives were tested for their antimicrobial activity against the bacteria: Staphylococcus aureus, Escherichia coli, Listeria innocua, Pseudomonas aeruginosa, Salmonella enterica Typhimurium, Salmonella enterica ssp. enterica, and Bacillus cereus. Minimum inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) values were determined using concentrations from 220 to 3.44 μg mL-1. Most of the tested compounds presented MIC values ≤220 μg mL-1 for all the bacteria used in the assays. The molecular properties of the compounds were computed with the PM6 method. Through principle components analysis, the natural phenols and their semisynthetic derivatives with higher antimicrobial potential were grouped.

Palladium-Catalyzed Fluoroalkylative Cyclization of Olefins

A palladium-catalyzed fluoroalkylative cyclization of olefins with readily available Rf-I reagents to afford the corresponding fluoroalkylated 2,3-dihydrobenzofuran and indolin derivatives with moderate to excellent yields is reported. This novel procedure provides an efficient method for the construction of Csp3-CF2 and C-O/N bonds in one step. A wide range of functional groups are tolerated. It is proposed that a radical/SET (single electron transfer) pathway proceeding via the fluoroalkyl radical may be involved in the catalytic cycle.

Boosting effect of ortho-propenyl substituent on the antioxidant activity of natural phenols

Seven new antioxidants derived from natural or synthetic phenols have been designed as alternatives to BHT and BHA antioxidants. Influence of various substituents at the ortho, meta and para positions of the aromatic core of phenols on the bond dissociation enthalpy of the ArO-H bond was evaluated using a DFT method B3LYP/6-311++G(2d,2p)//B3LYP/6-311G(d,p). This prediction highlighted the ortho-propenyl group as the best substituent to decrease the bond dissociation enthalpy (BDE) value. The rate constants of hydrogen transfer from these phenols to DPPH radical in a non-polar and non-protic solvent have been measured and were found to be in agreement with the BDE calculations. For o-propenyl derivatives from 2-tert-butyl-4-methylphenol, BHA, creosol, isoeugenol and di-o-propenyl p-cresol, fewer radicals were trapped by a single phenol molecule, i.e. a lower stoichiometric number. Reaction mechanisms involving the evolution of the primary phenoxyl radical ArO are proposed to rationalise these effects.

O-eugenol: A versatile molecule for production of polyfunctional alkenes via organometallic catalysis

In this study, the synthesis and cross metathesis of o-eugenol (2-allyl-6-methoxy phenol) has been investigated. Synthesis was conducted through two stages of reaction. The first step in the synthetic procedure was to obtain the intermediate 1-but-3-enyl-2-methoxy benzene. Then the heating of the obtained intermediate will initiate will initiate a [3,3] sigmatropic rearrangement to give the o-eugenol with a good yield. The ruthenium-catalyzed cross-metathesis of o-eugenol derivatives with electron deficient olefins including methyl acrylate, acrylonitrile and acrylamides was also reported. In addition the polymerization of 1-allyl-2-(allyloxy)-3-methoxybenzene was possible by acyclic diene metathesis and this allowed to synthesize a polymer from a natural substrate. All the resulting structures were supported by the spectroscopic data.

CLAISEN REARRANGEMENT OF ALLYL ARYL ETHERS CATALYSED BY ALKALINE-EARTH-METAL SALT

Disclosed is an effective catalytic process for carrying out a Claisen rearrangement reaction, comprising reacting an allyl aryl ether in the presence of a metal salt catalyst, wherein the metal salt catalyst is an alkaline-earth-metal triflate salt or an alkaline-earth-metal triflimide salt, wherein the alkaline-earth-metal is selected from a group consisting of magnesium (Mg), calcium (Ca), strontium (Sr) and barium (Ba).

Eugenol synthesis method

The invention belongs to the field of organic synthesis and particularly relates to a eugenol synthesis method. According to the eugenol synthesis method, guaiacol and allyl chloride are used as raw materials and are subjected to a catalytic reaction through a catalyst THLD to generate eugenol; an experiment testifies that the eugenol is synthesized by using the novel composite catalyst THLD, so that the conversion rate of the guaiacol and the yield of the eugenol are greatly improved, the conversion rate of the guaiacol reaches to 98 percent and the yield of the eugenol reaches to 88 percent.

A diastereoselective route to trans-2-aryl-2,3-dihydrobenzofurans through sequential cross-metathesis/isomerization/allylboration reactions: Synthesis of bioactive neolignans

A new highly diastereoselective synthetic route to trans-2,3-dihydrobenzofuran systems, in particular those bearing an aryl substituent at the C2 position, is described. The cornerstone of our strategy is the implementation of a cross-metathesis/isomerization/allylboration sequence starting from 2-allyl-substituted phenols and aldehydes. After an intramolecular Mitsunobu cyclization step, the anti-homoallylic alcohols allow the synthesis of the desired skeleton in a stereoselective fashion. As an illustration, we used this strategy for the preparation of the dihydrodehydrodiconiferyl alcohol (1a), a natural dihydrobenzofuran neolignan, as well as for a formal synthesis of its O-demethylated derivative 1b. An enantioselective version of this approach employing a chiral phosphoric acid in the allylboration step is also studied.

PROCESS FOR PREPARING SYNTHETIC PARA-EUGENOL

Processes are provided for preparing synthetic para-eugenol and polysiloxane- polycarbonate copolymers including the synthetic para-eugenol. In an embodiment, a process for synthesizing para-eugenol can comprise: a) hydrolyzing methyl 5-allyl-3- methoxysalicylate to form 5-allyl-3-methoxysalicylic acid; b) decarboxylating the 5-allyl-3- methoxysalicylic acid to form a product comprising para-eugenol. The polysiloxane- polycarbonate copolymer prepared by the process may be isolated by, for example, anti- solvent precipitation followed by vacuum drying.