Isolation and Spatial Structure of 5,7-Dihydroxy-6,3′,4′-Trimethoxyflavone

Isolation and Spatial Structure of 5,7-Dihydroxy-6,3′,4′-Trimethoxyflavone Full article

Journal

Eurasian Journal of Chemistry
ISSN: 2959-0663 , E-ISSN: 2959-0671

Output data

Year: 2023, Volume: 109, Number: 1, Pages: 13-19 Pages count : 7 DOI: 10.31489/2959-0663/1-23-1

Tags

NMR spectroscopy, IR spectroscopy, X-ray analysis, quantum chemistry, Artemisia semiarida, endemic, 5,7-dihydroxy-6,3′,4′-trimethoxyflavone, eupatilin, phenolic compounds.

Authors

Turdybekov Кoblandy M. ¹ , Rakhimova Bibilul B. ² , Makhmutova Almagul S. ² , Gatilov Yurii V. ³ , Adekenov Sergazy M. ⁴

Affiliations

1	Karagandy University of the name of academician E.A. Buketov
2	Karaganda Medical University, 40 Gogolya St., Karaganda, 100000, Kazakhstan
3	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of Siberian Branch of Russian Academy of Sciences
4	JSC “International Research and Production Holding “Phytochemistry”

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.

Turdybekov К.M. , Rakhimova B.B. , Makhmutova A.S. , Gatilov Y.V. , Adekenov S.M.
Isolation and Spatial Structure of 5,7-Dihydroxy-6,3′,4′-Trimethoxyflavone
Eurasian Journal of Chemistry. 2023. V.109. N1. P.13-19. DOI: 10.31489/2959-0663/1-23-1 WOS Scopus РИНЦ

Submitted:	Nov 11, 2022
Accepted:	Feb 2, 2023
Published online:	Mar 6, 2023

Web of science	WOS:000967529100003
Scopus	2-s2.0-85152888916
Elibrary	53700479
OpenAlex	W4323777699