6-Hydroxyisocaryophyllene and isocaryophyllenic acid from birches vegetative buds

  • Dmitriy Nikolaevich Vedernikov St. Petersburg State Forest Technical University named after S.M.Kirov Email: Dimitriy-4@yandex.ru
  • Svetlana Vitalievna Teplyakova St. Petersburg State Forest Technical University named after S.M.Kirov Email: chooh@bk.ru
  • Olesya Valerievna Khoroshilova Saint-Petersburg State University, Institute of Chemistry of St. Petersburg State University Email: o_hkorosh@mail.ru
Keywords: 6-hydroxyisocaryophyllene, epoxide of 6-hydroxyisocaryophyllene, isocaryophyllenic, caryophyllenic acid, vegetative buds of birch, NMR spectroscopy, X-ray diffraction analysis, gas chromatography – mass spectrometry

Abstract

The new isocaryophyllene derivatives were first detected in the birch vegetative buds. The structure of 6-hydroxyisocaryophyllene [(1R,4Z, 6R, 9S)-8-methylene-11,11-dimethylbicyclo[7.2.0]undec-4-ene-6-ol] isolated from the Betula pendula Roth. birch buds was determined by NMR spectroscopy.  The structures of caryophyllenic acid and isocaryphyllenic acid isolated from the Betula grandifolia Litv., B. albo-sinensis Burk., B. fusca Pall.ex Georg, B. obscura A. Kotula, B. litwinowii Doluch., B. hallii Howell, B. grandifolia Litv. birch buds was determined by X-ray diffraction analysis. The physico-chemical characteristics and NMR data of 6-hydroxyisocaryophyllene, epoxide of 6-hydroxyisocaryophyllene and all the isolated acids are given.  The gas chromatographic retention indices of all identified compounds were determined.

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Author Biographies

Dmitriy Nikolaevich Vedernikov, St. Petersburg State Forest Technical University named after S.M.Kirov
Department of Technology of Wood Chemical Products, Wood Chemistry and Biotechnology, Professor, D.Sc., Associate Professor
Svetlana Vitalievna Teplyakova, St. Petersburg State Forest Technical University named after S.M.Kirov
Department of Technology of Wood Chemical Products, Wood Chemistry and Biotechnology, graduate student
Olesya Valerievna Khoroshilova, Saint-Petersburg State University, Institute of Chemistry of St. Petersburg State University
graduate student, specialist of RSA

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Published
2018-03-26
How to Cite
1. Vedernikov D. N., Teplyakova S. V., Khoroshilova O. V. 6-Hydroxyisocaryophyllene and isocaryophyllenic acid from birches vegetative buds // Chemistry of plant raw material, 2018. № 3. P. 115-122. URL: https://journal.asu.ru/cw/article/view/3717.
Section
Low-molecular weight compounds