2-Ethoxyphenol

• CAS: 94-71-3
• Catalog Number: ACM94713-1
• Category: Main Products
• Molecular Weight: 138.16
• Molecular Formula: C8H10O2
• Synonyms: Tamsulosin Impurity 3
• Boiling Point: 219.4 °C at 760 mmHg
• Melting Point: 20-25 °C
• Flash Point: 91°C
• Appearance: Colorless to yellow clear liquid

Case Study

Liquid-liquid equilibrium studies of 2-ethoxyphenol

Alonso Tristán, Cristina, et al. 13th National and 4th International Conference in Engineering Thermodynamics

Liquid-liquid equilibrium (LLE) curves of critical protein systems (2-methoxyphenol or 2-ethoxyphenol + n-alkane mixtures) were obtained using laser scattering techniques. All systems exhibited upper critical solution temperatures (UCST). Furthermore, the top of the LLE curve was relatively flat, and its symmetry depended on the size of the alkane. The UCST increased almost linearly with the number of carbon atoms in the n-alkane. When a second alkoxy functional group was added to the aromatic molecule, the strong intermolecular interactions resulting from hydrogen bonding in phenol and aniline mixtures were significantly reduced, and this reduction was greater with increasing alkoxy group volume.
Before use, the liquids were stored in containers with molecular sieves. Density measurements were performed using a vibrating tube densimeter. A careful survey of literature data showed that no ρ value has been previously reported for the 2-ethoxyphenol. Melting points were measured using a modulated differential scanning calorimeter (MDSC). Sealing prevented sample volatilization or mass loss due to errors. A microbalance with a repeatability of 0.015 mg was used to weigh the sealed pans. Water content was determined by the Karl-Fischer method. The estimated relative standard uncertainty of the corresponding measurements was 0.02.

Study of Rhodococcus strains that degrade 2-ethoxyphenol

Karlson, U., et al. Journal of bacteriology 175.5 (1993): 1467-1474.

A red, rod-shaped bacterium capable of growing on 2-ethoxyphenol and 4-methoxybenzoic acid as the sole carbon and energy sources was isolated and identified as *Rhodococcus rhodochrous* strain 116. Both growth substrates induced the production of different cytochrome P450 enzymes: 2-ethoxyphenol induced cytochrome P-450O1, while 4-methoxybenzoic acid induced cytochrome P-450R. Both 2-ethoxyphenol (K = 4.2 ± 0.3 μM) and 2-methoxyphenol (K = 2.0 ± 0.1 μM) induced typical type I difference spectra in cytochrome P-450RR1, but 4-methoxybenzoic acid or 4-ethoxybenzoic acid did not. These cytochromes appear to catalyze the O-dealkylation of their respective substrates. The O-dealkylation products are further metabolized by ortho-cleavage enzymes, the expression of which is also regulated by the respective aromatic ethers.
Cultures were enriched for organisms capable of degrading ethoxyaromatic compounds by batch culture with rotary shaking at 30°C. M9 minimal medium containing 10% activated sludge was supplemented with 2-ethoxyphenol and 4-ethoxybenzoic acid according to the following schedule: 0.5 mM for 2 months, 1 mM for 1 month, and 2 mM for 1 month. Thereafter, the culture broth contained concentrated compounds at a concentration of 5 mM. The microorganism was typically cultured in M9 medium at 30°C using one of the following carbon sources: 2-ethoxyphenol, 4-ethoxybenzoic acid, or succinate. At the end of the logarithmic growth phase, cells were harvested by centrifugation, washed, and resuspended in buffer A.

Study of 2-ethoxyphenol as an intermediate in guaiacol conversion

Mai, Fuhang, et al. RSC advances 9.5 (2019): 2764-2771.

The conversion of guaiacol was investigated using a catalyst in supercritical ethanol at 300 °C. Guaiacol was completely consumed, yielding 16.7% aromatic ethers and 80.0% alkylphenols. Experimental results indicated that catechol and 2-ethoxyphenol were intermediates. Meanwhile, WO3 sites played a crucial role in the guaiacol conversion, and Brønsted acid sites on H2WO4 enhanced the conversion process and favored high selectivity towards tert-butylphenol. Finally, a possible reaction pathway involving transetherification and alkylation processes in guaiacol conversion was proposed.
Under the same conditions, potential intermediates of the guaiacol conversion reaction (such as catechol, 2-ethoxyphenol, phenol, and benzyl alcohol) were tested. The selectivity of 2-ethoxyphenol gradually decreased with time, suggesting that 2-ethoxyphenol might also be an intermediate. The product distribution using 2-ethoxyphenol as a reactant was indeed similar to that of guaiacol conversion, although 12% of 2-ethoxyphenol remained unconverted, and the overall selectivity of alkylphenols decreased. However, the product distribution of phenol conversion was significantly different from that of guaiacol conversion, indicating that phenol was not an intermediate.

The antibacterial activity of iron complexes of 2-ethoxyphenol

Arumugam, Meyyappan, Parasuraman Jaisankar, and Joydeep Mukherjee. Natural Product Research 26.20 (2012): 1942-1944.

Iron(III) complexes of certain smoky flavor compounds (2-allyloxyphenol, guaiacol, eugenol, and 2-ethoxyphenol) were synthesized and characterized using UV-Vis spectroscopy and ESI mass spectrometry. The ligand-to-metal binding ratio was determined to be 1:1 using the Job's method. The antibacterial activity of the ligand-iron complexes against *Bacillus subtilis*, *Escherichia coli*, *Staphylococcus aureus*, and *Pseudomonas aeruginosa* was studied. This activity was compared to that of the free ligands. This study, for the first time, confirms that smoky flavor compounds not only form complexes with iron that may delay food spoilage, but also that some of these complexes exhibit antibacterial activity after complex formation, compared to the inactive free ligands.
The antibacterial activity of the free ligands and complexes was compared using the agar diffusion method. As free ligands, guaiacol and 2-ethoxyphenol showed no antibacterial activity at 0.1 M, but as iron(III) complexes, they were active against *Bacillus subtilis*, *Escherichia coli*, *Staphylococcus aureus*, and *Pseudomonas aeruginosa* at the same concentration. Guaiacol and 2-ethoxyphenol were chosen to demonstrate the antibacterial activity after complexation. However, the antibacterial effect of eugenol and 2-allyloxyphenol complexes was limited.

Custom Q&A

What is the molecular formula of 2-Ethoxyphenol?

The molecular formula of 2-Ethoxyphenol is C8H10O2.

What is the molecular weight of 2-Ethoxyphenol?

The molecular weight of 2-Ethoxyphenol is 138.16 g/mol.

What is the IUPAC name of 2-Ethoxyphenol?

The IUPAC name of 2-Ethoxyphenol is 2-ethoxyphenol.

What is the CAS number of 2-Ethoxyphenol?

The CAS number of 2-Ethoxyphenol is 94-71-3.

What is the appearance of 2-Ethoxyphenol?

2-Ethoxyphenol is a colorless to pale yellow liquid.

What is the density of 2-Ethoxyphenol?

The density of 2-Ethoxyphenol is 1.073 g/cm³ at 25 °C (77 °F).

What is the melting point of 2-Ethoxyphenol?

The melting point of 2-Ethoxyphenol is 20-25 °C (68-77 °F).

Is 2-Ethoxyphenol soluble in water?

Yes, 2-Ethoxyphenol is soluble in water.

What is the flash point of 2-Ethoxyphenol?

The flash point of 2-Ethoxyphenol is 108 °C (226 °F).

What precautions should be taken when handling 2-Ethoxyphenol?

It should be kept away from heat, sparks, and open flames, and stored in a cool, dry place. Adequate ventilation and appropriate protective clothing and gloves should be used when handling 2-Ethoxyphenol. Contact with eyes, skin, and clothing should be avoided.