Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one
Issued Date
2025-03-01
Resource Type
eISSN
20569890
Scopus ID
2-s2.0-105002812449
Journal Title
Acta Crystallographica Section E: Crystallographic Communications
Volume
81
Start Page
219
End Page
223
Rights Holder(s)
SCOPUS
Bibliographic Citation
Acta Crystallographica Section E: Crystallographic Communications Vol.81 (2025) , 219-223
Suggested Citation
Saekee A., Kuhakarn C., Chakarawet K., Hongthong S. Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one. Acta Crystallographica Section E: Crystallographic Communications Vol.81 (2025) , 219-223. 223. doi:10.1107/S2056989025001070 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/109747
Title
Synthesis and crystal structure of 5,10-dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one
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Abstract
5,10-Dihydroxy-9-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one, C24H24O6 (2), is a prenylated xanthone that was synthesized from 5,9,10-trihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-2H,6H-pyrano[3,2-b]xanthen-6-one or macluraxanthone (1), a known compound isolated from Garcinia schomburgkiana Pierre. The present study describes the synthesis of compound 2 by methylation reaction of 1, and its crystallographic characterization. Compound 2 features a planar xanthone core and a bent pyrano ring adopting a half-boat conformation. An intermolecular O - H⋯O hydrogen bond between the hydroxyl hydrogen donor and the ketone acceptor organizes the molecules into a one-dimensional network along the b-axis direction. Perpendicular to this network, π-π stacking interactions form the three-dimensional supramolecular architecture. These two key intermolecular interactions are distinctly revealed in the Hirshfeld surface analysis.