579-60-2

Basic information

• Product Name: O-EUGENOL
• Synonyms: 2-Methoxy-6-(2-propenyl)phenol;2-Methoxy-6-allylphenol;3-(2-Hydroxy-3-methoxyphenyl)propene;3-Allylguaiacol;O-EUGENOL;2-ALLYL-6-METHOXYPHENOL;6-ALLYL-2-METHOXYPHENOL;6-allylguaicol
• CAS NO: 579-60-2
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: 209-444-1
• Mol File: 579-60-2.mol
• Article Data: 38

Chemical Properties

• Melting Point: 81 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 119-121 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow liquid
• Density: 1.068 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0129mmHg at 25°C
• Refractive Index: n20/D 1.538(lit.)
• PKA: 10.30±0.10(Predicted)
• CAS DataBase Reference: O-EUGENOL(CAS DataBase Reference)
• NIST Chemistry Reference: O-EUGENOL(579-60-2)
• EPA Substance Registry System: O-EUGENOL(579-60-2)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 23-26-36
• WGK Germany: 3
• Hazardous Substances Data: 579-60-2(Hazardous Substances Data)

Usage

Description

O-Eugenol, also known as 2-methoxy-4-(2-propenyl)phenol, is an organic compound that belongs to the family of phenylpropenes. It is a clear yellow liquid with a distinctive spicy and floral scent. O-Eugenol is commonly found in the essential oils of various plants, such as clove oil, basil oil, and cinnamon leaf oil. Its chemical structure allows it to interact with various biological systems, making it a versatile compound with a wide range of applications.

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 
• 108-88-3 toluene 
• 59744-45-5 1-allyl-2-(allyloxy)-3-methoxybenzene 
• 90-05-1 2-methoxy-phenol 
• 107-05-1 3-chloroprop-1-ene 
• 120-80-9 benzene-1,2-diol 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 96619-89-5 3-methoxy-2-(2-propenyloxy)benzoic acid, methyl ester 
• 6342-70-7 3-methoxymethylsalicylate 
• 877-22-5 3-methoxysalicylic acid 
• 106-95-6 allyl bromide 
• 74-88-4 methyl iodide 
• 23343-06-8 2-allyloxy-3-methoxy-benzaldehyde 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 2173-78-6 2-Allyl-6-methoxyphenyl acetate 
• 875841-21-7 1-allyl-2-(2-chloro-ethoxy)-3-methoxy-benzene 
• 19754-21-3 1-allyl-2,3-dimethoxy-benzene 
• 1076-55-7 (E/Z)-2-(1-Propenyl)-6-methoxyphenol 
• 86153-98-2 2-methoxy-6-propylphenol 
• 35151-42-9 1-Methoxy-2-methoxymethoxy-3-(prop-2-enyl)benzene 
• 29275-83-0 2-methoxy-6-[(E)-1-propenyl]phenol 
• 866528-97-4 Trifluoro-methanesulfonic acid 2-methoxy-6-((E)-propenyl)-phenyl ester 
• 404356-64-5 3-(3-methoxy-2-methoxymethoxy-phenyl)-propane-1,2-diol 
• 404356-49-6 2-(2-benzofuran-2-yl-2-benzyloxy-ethyl)-6-methoxy-phenol 
• 404356-65-6 2-[1-benzyloxy-2-(3-methoxy-2-methoxymethoxy-phenyl)-ethyl]-benzofuran 
• 868258-16-6 (2S,3S)-4-((E)-3-((R)-1-carboxy-2-(3,4-dimethoxyphenyl)ethoxy)-3-oxoprop-1-en-1-yl)-2-(3,4-dimethoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid 
• 55757-14-7 (2S,3S)-methyl 2-(3,4-dimethoxyphenyl)-4-((E)-3-(((R)-3-(3,4-dimethoxyphenyl)-1-methoxy-1-oxopropan-2-yl)oxy)-3-oxoprop-1-en-1-yl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylate 
• 1283147-55-6 (R)-1-oxo-1-(pyrrolidin-1-yl)propan-2-yl 2-(2-(benzyloxy)-3-methoxyphenyl)acetate 

Relevant articles and documents

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.

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.