Structural Characterization of Mono and Dihydroxylated Umbelliferone Derivatives.

Rubén Seoane-Rivero,José Manuel Laza,Rodrigo Navarro,Beñat Artetxe,Juan M Gutiérrez-Zorrilla,Estibaliz Ruiz-Bilbao,Ángel Marcos-Fernandez,José María Cuevas,José Luis Vilas-Vilela

doi:10.3390/molecules25153497

Abstract

Coumarin derivatives are a class of compounds with a pronounced wide range of applications, especially in biological activities, in the medicine, pharmacology, cosmetics, coatings and food industry. Their potential applications are highly dependent on the nature of the substituents attached to their nucleus. These substituents modulate their photochemical and photophysical properties, as well as their interactions in their crystalline form, which largely determines the final field of application. Therefore, in this work a series of mono and dihydroxylated coumarin derivatives with different chemical substituents were synthesized and characterized by UV-Visible spectroscopy, thermal analysis (differential scanning calorimetry (DSC) and TGA), 1H NMR and X-Ray Diffraction to identify limitations and possibilities as a function of the molecular structure for expanding their applications in polymer science.

Highlights

IntroductionCoumarins (chromen-2-ones) are a family of benzopyrones widely distributed in nature
Coumarins are a family of benzopyrones widely distributed in nature
As the experimental UV-Vis spectra of coumarins have been obtained in aqueous solution, the solvent effects of water were considered with the conductor-like polarizable continuum model (PCM)

Summary

Introduction

Coumarins (chromen-2-ones) are a family of benzopyrones widely distributed in nature. 1902, when Ciamician and Silber found that coumarin had the ability to be photoreactive, the photo-cyclodimerization and photo-cleavage of this product has received a lot of attention by several investigation groups [1,2,3,4]. Their structure are a class of lactones based on a benzene ring fused to α-pyrone ring, as can be seen in Scheme 1A [5,6]. Coumarins represent an important family of naturally occurring and/or synthetic oxygen-containing heterocycles, bearing a typical benzopyrone framework. When irradiated at >300 nm, a [2 + 2] cycloaddition reaction takes place, forming a cyclobutane ring; in contrast, irradiating at 254 nm a photo-scission reaction leads to the original coumarin structures (Scheme 1B) [7,8,9,10]

Methods

Results

Conclusion