Synthesis of xanthohumol and xanthohumol-d3 from naringenin

Joanna Andrusiak; Kinga Mylkie; Małgorzata Wysocka; Jacek Ścianowski; Andrzej Wolan; Marcin Budny

doi:10.1039/D1RA05443K

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Synthesis of xanthohumol and xanthohumol-d₃ from naringenin†

Joanna Andrusiak,^ab Kinga Mylkie,^cd Małgorzata Wysocka,^b Jacek Ścianowski,

^a Andrzej Wolan^ab and Marcin Budny

*^b

Author affiliations

* Corresponding authors

^a Department of Organic Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Toruń, Poland

^b Synthex Technologies Sp. z o.o., Gagarina 7/134B, 87-100 Toruń, Poland
E-mail: budny@synthex.com.pl

^c Department of Biomedical and Polymer Chemistry, Faculty of Chemistry, Nicolaus Copernicus University, Gagarina 7, 87-100 Toruń, Poland

^d Noctiluca S.A., Gagarina 7/41B, 87-100 Toruń, Poland

Abstract

A six-step synthesis of xanthohumol (1a) and its d₃-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α,β-conjugated ketone system. Compound 1b was used as an internal standard in stable isotope dilution assays of 1a in two Polish beers.

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Article information

DOI: https://doi.org/10.1039/D1RA05443K
Article type: Paper
Submitted: 15 Jul 2021
Accepted: 13 Aug 2021
First published: 31 Aug 2021
This article is Open Access

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RSC Adv., 2021,11, 28934-28939

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Synthesis of xanthohumol and xanthohumol-d₃ from naringenin

J. Andrusiak, K. Mylkie, M. Wysocka, J. Ścianowski, A. Wolan and M. Budny, RSC Adv., 2021, 11, 28934 DOI: 10.1039/D1RA05443K

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