{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,2,21]],"date-time":"2025-02-21T21:49:35Z","timestamp":1740174575535,"version":"3.37.3"},"reference-count":34,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2022,9,27]],"date-time":"2022-09-27T00:00:00Z","timestamp":1664236800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2022,9,27]],"date-time":"2022-09-27T00:00:00Z","timestamp":1664236800000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"Bio-Based Industries Joint Undertaking (BBI JU) under the European Union's Horizon 2020 research and innovation program","award":["744349"],"award-info":[{"award-number":["744349"]}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2022,9,19]]},"published-print":{"date-parts":[[2022,10,1]]},"abstract":"<jats:p>The title compound, C<jats:sub>13<\/jats:sub>H<jats:sub>16<\/jats:sub>O<jats:sub>3<\/jats:sub> [<jats:bold>GE-isoEu<\/jats:bold>; systematic name: 2-({2-methoxy-4-[(<jats:italic>E<\/jats:italic>)-1-propen-1-yl]phenoxy}methyl)oxirane], which crystallizes in the triclinic <jats:italic>P<\/jats:italic>\\overline{1} space group, was synthesized in one step from <jats:italic>iso-<\/jats:italic>eugenol, a bio-based phenylpropanoid, with an excess of epichlorohydrin. Colourless prismatic crystals suitable for X-ray diffraction were obtained from a mixture of ethyl acetate and cyclohexane, during purification by column chromatography on silica gel. <jats:bold>GE-isoEu<\/jats:bold>, which corresponds to the <jats:italic>trans<\/jats:italic> isomer of the monoglycidyl ether of <jats:italic>iso-<\/jats:italic>eugenol, is based on a 1,2,4-trisubstituted benzene ring by diglycidyl ether, methoxy and 1-(<jats:italic>E<\/jats:italic>)-propenyl groups, respectively. In the crystal, molecules are organized through offset <jats:italic>\u03c0<\/jats:italic>-stacking interactions. Chemically, <jats:bold>GE-isoEu<\/jats:bold> constitutes an intermediate in the synthesis protocol of 2-[3-methoxy-4-(2-oxiranylmethoxy)phenyl]-3-methyloxirane (<jats:bold>GEEp-isoEu<\/jats:bold>), a diepoxydized monomer used in the manufacturing of thermosetting resins and intended for the elaboration of bio-composites.<\/jats:p>","DOI":"10.1107\/s2056989022009264","type":"journal-article","created":{"date-parts":[[2022,9,27]],"date-time":"2022-09-27T07:46:04Z","timestamp":1664264764000},"page":"1052-1055","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Crystal structure of the monoglycidyl ether of isoeugenol"],"prefix":"10.1107","volume":"78","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4416-7510","authenticated-orcid":true,"given":"H\u00e9l\u00e8ne","family":"Cattey","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gilles","family":"Boni","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sylvie","family":"Pourchet","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7870-1881","authenticated-orcid":true,"given":"Laurent","family":"Plasseraud","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"329","published-online":{"date-parts":[[2022,9,27]]},"reference":[{"key":"dj2051_bb1","doi-asserted-by":"crossref","first-page":"1082","DOI":"10.1021\/cr3001274","volume":"114","author":"Auvergne","year":"2014","journal-title":"Chem. 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