Abstract
In the title compound, C19H19NO5, the amide carbonyl O atom is positioned anti to the other two carbonyl O atoms. The 4-hy-droxy-hydro-cinnamate fragment is disordered over two positions with an occupancy ratio of 0.729 (12):0.271 (12). The N-(C=O)-C plane of the acetamide group and the acetate O-(C=O)-C plane are almost co-planar; the acetamide plane makes dihedral angles of 1.9 (6) and 16.0 (19)°, respectively, with the acetate planes of the major and minor occupancy components. In the crystal, N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular sheet structure parallel to (102).
Highlights
In the title compound, C19H19NO5, the amide carbonyl O atom is positioned anti to the other two carbonyl O atoms
The 4-hydroxyhydrocinnamate fragment is disordered over two positions with an occupancy ratio of 0.729 (12):0.271 (12)
Tyrosinase is a key enzyme present in melanocytes, which is involved in the biosynthesis of melanin
Summary
Hydroxy-substituted aromatic compounds with additional ester and amide functionalities have been reported to be potential tyrosinase inhibitors (Miliovsky et al, 2013; Takahashi & Miyazawa, 2011). Tyrosinase is a key enzyme present in melanocytes, which is involved in the biosynthesis of melanin. The abnormal production and accumulation of melanin causes a number of hyperpigmentation disorders such as freckles, melasma, lentigo senilis and pigmented acne scars (Lynde et al, 2006; Cullen, 1998). The synthesis and tyrosinase inhibitory activity of hydroxy-substituted phenyl esters is currently an ongoing research topic in our lab (Ashraf et al, 2015). In view of the tyrosinase inhibitory potential of hydroxy-substituted aromatic compounds, the title compound (Fig. 1) has been synthesized and characterized by single crystal X-ray diffraction.
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