Oppi Briefs New Synthesis of Hydrangetin and Collbsin

Maes, Dominick; Vervisch, Stijn; Kimpe, Norbert De

doi:10.1080/00304940709458594

Cited by 4 publications

(2 citation statements)

References 12 publications

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“…However, it differs from those obtained by Curini et al (255–256 °C) and by Liu and Tian (253–255 °C). Melting point temperatures of isomers 8 and 9 are comparable to those obtained by Curini et al, which go from 97 up to 99 °C, while melting points of isomers 10 and 11 are not comparable to those obtained by Curini et al (67–69 °C), Kim et al (66.5–67 °C), and Maes et al (67–68 °C). Differences among the melting temperatures obtained in this work and those reported in the literature might be explained as a result of the compound’s purity and purification method.…”

Section: Methodssupporting

confidence: 68%

“…As a result, several routes for chemical synthesis have been proposed. For example, Curini et al and Maes et al studied and reported routes of chemical synthesis with overall molar yields as high as 24.6 and 6.8%, respectively. However, in the high-yield synthesis procedure reported by Curini and co-workers, two isomers were obtained and not enough evidence about their respective identification was reported.…”

Section: Introductionmentioning

confidence: 99%

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Solubility of Collinin and Isocollinin in Pressurized Carbon Dioxide: Synthesis, Solubility Parameters, and Equilibrium Measurements

et al. 2019

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Collinin is a derivative of coumarin that has shown remarkable potential against cancer, tuberculosis, periodontitis, and other prevalent diseases, and is usually extracted from plants of the Rutaceae family at a very low yield. In this work, collinin and a position-isomer herein called isocollinin were synthesized at different scales (from 1 to 50 g of precursor) by a route consisting of two parallel and two sequential chemical reactions. The isomers were characterized by 1H NMR, 13C NMR, nuclear Overhauser enhancement spectroscopy NMR, melting temperature, and melting enthalpy. For each isomer, the Hansen solubility parameters and the radius of its solubility sphere were experimentally determined by solubility tests in 15 common solvents and two solvent blends. The solubility of each isomer in pressurized CO2 was determined at 30 and 50 °C from 72.2 to 112.9 bar, by an in situ high-pressure spectrometry technique, which was validated with the anthracene–CO2 system. The solubility of both isomers in CO2 increased with pressure in the range of temperatures and pressures considered, but that of collinin exhibited an asymptotic behavior around 80.8 and 104.8 bar, at 30 and 50 °C, respectively.

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