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4′,5-Dihy­droxy-7-meth­oxy­flavanone dihydrate

The title compound, C(16)H(14)O(5)·2H(2)O [systematic name: 5-hy­droxy-2-(4-hy­droxy­phen­yl)-7-meth­oxy­chroman-4-one dihydrate], is a natural phytoalexin flavone isolated from the native chilean species Heliotropium taltalense and crystallizes with an organic mol­ecule and two water mol­ecules in...

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Autores principales: Brito, Iván, Bórquez, Jorge, Simirgiotis, Mario, Cárdenas, Alejandro, López-Rodríguez, Matías
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3254395/
https://www.ncbi.nlm.nih.gov/pubmed/22259537
http://dx.doi.org/10.1107/S1600536811051221
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author Brito, Iván
Bórquez, Jorge
Simirgiotis, Mario
Cárdenas, Alejandro
López-Rodríguez, Matías
author_facet Brito, Iván
Bórquez, Jorge
Simirgiotis, Mario
Cárdenas, Alejandro
López-Rodríguez, Matías
author_sort Brito, Iván
collection PubMed
description The title compound, C(16)H(14)O(5)·2H(2)O [systematic name: 5-hy­droxy-2-(4-hy­droxy­phen­yl)-7-meth­oxy­chroman-4-one dihydrate], is a natural phytoalexin flavone isolated from the native chilean species Heliotropium taltalense and crystallizes with an organic mol­ecule and two water mol­ecules in the asymmetric unit. The 5-hy­droxy group forms a strong intra­molecular hydrogen bond with the carbonyl group, resulting in a six-membered ring. In the crystal, the components are linked by O—H⋯O hydrogen bonds, forming a three-dimensional network. The 4-hy­droxy­phenyl benzene ring is bonded equatorially to the pyrone ring, which adopts a slightly distorted sofa conformation. The title compound is the hydrated form of a previously reported structure [Shoja (1990 ▶). Acta Cryst. C46, 1969–1971]. There are only slight variations in the mol­ecular geometry between the two compounds.
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spelling pubmed-32543952012-01-18 4′,5-Dihy­droxy-7-meth­oxy­flavanone dihydrate Brito, Iván Bórquez, Jorge Simirgiotis, Mario Cárdenas, Alejandro López-Rodríguez, Matías Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(16)H(14)O(5)·2H(2)O [systematic name: 5-hy­droxy-2-(4-hy­droxy­phen­yl)-7-meth­oxy­chroman-4-one dihydrate], is a natural phytoalexin flavone isolated from the native chilean species Heliotropium taltalense and crystallizes with an organic mol­ecule and two water mol­ecules in the asymmetric unit. The 5-hy­droxy group forms a strong intra­molecular hydrogen bond with the carbonyl group, resulting in a six-membered ring. In the crystal, the components are linked by O—H⋯O hydrogen bonds, forming a three-dimensional network. The 4-hy­droxy­phenyl benzene ring is bonded equatorially to the pyrone ring, which adopts a slightly distorted sofa conformation. The title compound is the hydrated form of a previously reported structure [Shoja (1990 ▶). Acta Cryst. C46, 1969–1971]. There are only slight variations in the mol­ecular geometry between the two compounds. International Union of Crystallography 2011-12-07 /pmc/articles/PMC3254395/ /pubmed/22259537 http://dx.doi.org/10.1107/S1600536811051221 Text en © Brito et al. 2012 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Brito, Iván
Bórquez, Jorge
Simirgiotis, Mario
Cárdenas, Alejandro
López-Rodríguez, Matías
4′,5-Dihy­droxy-7-meth­oxy­flavanone dihydrate
title 4′,5-Dihy­droxy-7-meth­oxy­flavanone dihydrate
title_full 4′,5-Dihy­droxy-7-meth­oxy­flavanone dihydrate
title_fullStr 4′,5-Dihy­droxy-7-meth­oxy­flavanone dihydrate
title_full_unstemmed 4′,5-Dihy­droxy-7-meth­oxy­flavanone dihydrate
title_short 4′,5-Dihy­droxy-7-meth­oxy­flavanone dihydrate
title_sort 4′,5-dihy­droxy-7-meth­oxy­flavanone dihydrate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3254395/
https://www.ncbi.nlm.nih.gov/pubmed/22259537
http://dx.doi.org/10.1107/S1600536811051221
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