3'-Hydroxyacetophenone: A Versatile Organic Compound with Diverse Applications

Introduction

3'-Hydroxyacetophenone is also known as m-hydroxyacetophenone or 3-hydroxyacetophenone. This compound is an organic compound belonging to the class of phenols. This compound, denoted by the chemical formula C8H8O2, is a critical intermediate in synthesising various pharmaceuticals, agrochemicals, and fine chemicals.

Solid-liquid equilibria for three binary mixtures research

4-Aminoacetophenone, 3- and 4-hydroxyacetophenone are intermediates in organic synthesis or pharmaceuticals. 4-Aminoacetophe-none is the product from the reaction of N-phenylacetamide in the solvent of benzene or methanol. These compounds have close boiling points, and a crystallization process is feasible for separation and purification. 3- and 4- Hydroxyacetophenone are isomers and products of the reaction 4-aminoacetophenone in aqueous solutions.

Solid–liquid equilibria (SLE) for three binary mixtures of N-phenylacetamide with 4-aminoacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone were measured using differential scanning calorimetry (DSC) by Kuo et al. Simple eutectic behaviours for all three systems were observed. The Wilson and UNIFAC activity coefficient models were employed to calculate the experimental results. The fractional transformation method that used the DSC experimental data and the theoretically based calculations to determine the eutectic compositions of solid-liquid equilibria was applied. The enthalpy generation rate and the fractional transformation were evaluated using Gray's model. New SLE data are reported in this study. The DSC experiment with the fractional transformation method is demonstrated as a fast and reliable way to determine the eutectic point of a binary mixture.

3-hydroxyacetophenone could be considered as a phytoanticipin.

Among other constitutive phenols, 3-hydroxyacetophenone has been detected in an uninfected carnation cultivar resistant to Fusarium oxysporum f. sp. dianthi, a fungus known to cause the main disease affecting this plant species.

When tested in vitro, the flavonoid glycosides only slightly inhibited F. oxysporum growth, while 3-hydroxyacetophenone proved very effective. Its inhibitory activity towards the fungus was also confirmed by in vivo experiments. 3- Hydroxyacetophenone is present both in the roots and in the stems in concentrations comparable to those which proved to be effective in the researcher's biological experiments. Surprisingly, 3-hydroxyacetophenone appeared to be the main phenol responsible for the constitutive resistance in the studied carnation cultivar. Its absence in the resistant carnation cv. Novada appears to indicate that 3-hydroxyacetophenone cannot be considered a ubiquitous effector of the resistance in Dianthus caryophyllus. It is clear, however, that the present case is another example in which plants can develop a passive defence system, concomitant with one of phytoalexins, based on the presence of constitutive phenols; from this point of view, 3-hydroxy acetophenone must be considered as a phytoanticipin.

References

[1]Curir P, Marchesini A, Danieli B, et al. 3-Hydroxyacetophenone in carnations is a phytoanticipin active against Fusarium oxysporum f. sp. dianthi[J]. Phytochemistry, 1996, 41(2): 447-450.

[2]Chen Y P, Tang M, Kuo J C. Solid–liquid equilibria for binary mixtures of N-phenylacetamide with 4-aminoacetophenone, 3-hydroxyacetophenone and 4-hydroxyacetophenone[J]. Fluid phase equilibria, 2005, 232(1-2): 182-188.

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