Isolation and Spatial Structure of 5,7-Dihydroxy-6,3′,4′-Trimethoxyflavone
Turdybekov K.M. Rakhimova B.B. Makhmutova A.S. Gatilov Y.V. Adekenov S.M.
2023
Eurasian Journal of Chemistry
2023#109Issue 113 - 19 pp.
The article presents the results of a chemical study of semi-dry wormwood (Artemisia semiarida), an endemic plant of Kazakhstan. The amount of extractive substances was obtained by extraction with chloroform from air-dried crushed above-ground part of the plant collected in the vegetative phase. The compound was isolated using a column chromatography method. Silica gel of the KSK brand was used with the ratio of the sum of substances – carrier = 1:10. When the column was eluted with a 13:7 petroleum ether – ethyl acetate mixture, a yellow crystalline substance of the composition C18H16O7 with m.p. 234–237° C was obtained (recrystallization from ethyl acetate). The structure of the obtained compound (5,7-dihydroxy-6,3′,4′-trimethoxyflavone or eupatilin) was established by analysis of IR and NMR spectra. The spatial structure of eupatilin was determined by X-ray diffraction. In the crystal structure of 5,7-dihydroxy-6,3′,4′-trimethoxyflavone the rotation of the phenyl ring relative to the main framework (chromene ring) was found to be only 4.1°. Four conformers with different rotations of the phenyl ring (the torsional angles of O1C2C1′C2′ are 30°, 140°, 210° and 320°, respectively) and small energy barriers (about 8.4 kJ/mol) can be realized in the free state of the molecule.
3′ , 4′-trimethoxyflavone , 5 , 7-dihydroxy-6 , Artemisia semiarida , endemic , eupatilin , IR spectroscopy , NMR spectroscopy , phenolic compounds , quantum chemistry , X-ray analysis
Text of the article Перейти на текст статьи
Karagandy University of the name of academician E.A. Buketov, Universitetskaya street, 28, Karaganda, 100024, Kazakhstan
Karaganda Medical University, Gogol str., 40, Karaganda, 100008, Kazakhstan
N.N. Vorozhtsov Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences, Lavrentiev Avenue, 9, Novosibirsk, 630090, Russian Federation
JSC “International Research and Production Holding “Phytochemistry”, Gazaliev str. 4, Karaganda, 100009, Kazakhstan
Karagandy University of the name of academician E.A. Buketov
Karaganda Medical University
N.N. Vorozhtsov Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
JSC “International Research and Production Holding “Phytochemistry”
10 лет помогаем публиковать статьи Международный издатель
Книга Публикация научной статьи Волощук 2026 Book Publication of a scientific article 2026