Method for synthesizing xanthohumol
AssigneePro Xn Sp. Z O.O.
InventorsJoanna Andrusiak, Kinga Mylkie, Andrzej Jan Wolan, Mariusz Jan Bosiak
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Abstract
A method for synthesizing xanthohumol (XN) from naringenin comprising includes the steps of acylating hydroxyl groups of a naringenin flavone moiety to obtain an acylation product, a reaction of conversion of the flavone moiety into a chalcone moiety, and subjecting the chalcone compound to a reaction of hydrolysis of its ester groups, and next to a reaction of substitution of a prenyl moiety of the chalcone moiety to obtain xanthohumol. The xanthohumol produced by this method can be purified using crystallisation.
Claims12
A method for synthesizing xanthohumol (XN), the method comprising the steps of:
- providing naringenin,
- acylating hydroxyl groups at carbons 7 and 4′ of a naringenin flavone moiety to obtain an acylation product,
- subjecting the acylation product to a reaction of alkylation of a free hydroxyl to an alkoxyl moiety and to a reaction of conversion of the naringenin flavone moiety into a chalcone moiety, in a presence of a non-nucleophilic base, in a polar aprotic solvent, to obtain a chalcone compound,
- subjecting the chalcone compound to:
- a reaction of hydrolysis of its ester groups at carbons 4, 4′ and 6 of the chalcone moiety to obtain hydroxyl groups, and next
- a reaction of substitution of a prenyl moiety at carbon 5′ of the chalcone moiety to obtain xanthohumol.
Dependencies are inferred from the claim text.