Description
2-Coumaranone (also named as Isophthalide, 3H-benzofuran-2-one) belongs to a class of organic compounds named as benzofuranones which exhibits mutagenic and carcinogenic activity. 2-Coumaranone has been used to study the effects of coumarins on 7,12-dimethyibenz(a)anthracene induced neoplasia of the rat mammary gland and as probe for detecting enzymes which hydrolyze 2-hydroxybenzofuran structures.
Reference
Y. S. Priya, K. Ramachandra Rao, P. V. Chalapathi, M. Satyavani, A. Veeraiah, Vibrational and UV spectroscopic studies of 2-coumaranone by experimental and density functional theory calculations, Journal of Molecular Structure, 2017, vol. 1144, pp. 535-544
Chemical Properties
WHITE TO LIGHT YELLOW CRYSTALLINE POWDER
Uses
2-Coumaranone has been used to study the effects of coumarins on 7,12-dimethyibenz(
a)anthracene induced neoplasia of the rat mammary gland. It was employed as probe for detecting enzymes which hydrolyze 2-hydroxybenzofuran structures.
Synthesis Reference(s)
The Journal of Organic Chemistry, 47, p. 2491, 1982
DOI: 10.1021/jo00133a055
Synthesis
Preparation of 2-coumarone (I) comprises reacting cyclohexanone (II) with carboxyl-containing acylating agent (III) to methyl 2-(2-oxo-cyclohexyl)-2-hydroxy-acetate (IV) and optional dehydration to a mixture (V) of methyl 2-oxo-cyclohexylidene-acetate and the enol-lactone of the acid; or direct conversion of (I) to (V); and catalytic gas phase dehydrogenation of (IV) or (V) to (I).
