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Natural crystalline fibers of (E)-(R)-4-thujanol: green kilogram production from a selected wild thyme. X-ray and NMR characterization of a spiral structure

dc.rights.licenseopenen_US
dc.contributor.authorMORVAN, Estelle
dc.contributor.authorKAUFFMANN, Brice
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorGRÉLARD, Axelle
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorLOQUET, Antoine
dc.contributor.authorDIXON, Anne-Julie
hal.structure.identifierChimie et Biologie des Membranes et des Nanoobjets [CBMN]
dc.contributor.authorDUFOURC, Erick J.
dc.contributor.authorRONTEIN, Denis
dc.date.accessioned2023-04-06T08:48:19Z
dc.date.available2023-04-06T08:48:19Z
dc.date.issued2022-11-01
dc.identifier.issn0926-6690en_US
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/172839
dc.description.abstractEn(E)-(R)-4-Thujanol present in thyme essential oils is an important aromatic ingredient for food, cosmetic and pharmaceutical applications. Until now, its extraction was challenging due to its low content in classical aromatic plants such as thyme or marjoram. Although this molecule is synthetically available, there is no production on an industrial scale because of very time-consuming and expensive chemical processes. We report here for the first time a new eco-responsible method to produce (E)-(R)-4-thujanol crystals on a kilogram scale. This new milestone is based on 2 fundamental research gaps: i) the selection of a wild thyme (Thymus vulgaris) for its high content of (E)-(R)-4-thujanol and its careful harvesting in the hills of French Provence and ii) a steam distillation producing an organic aromatic oil which aggregates spontaneously due to a favorable amphipathic partition at the air-water interface. Gas chromatography revealed a composition made of (E)-(R)-4-thujanol (76%), thymol (5%), β-myrcene (2,8%) and other minor monoterpenes. The white aggregate submitted to a cycle of sublimation/crystallization, led to accumulating translucent fibers made of (E)-(R)-4-thujanol (98%). X-ray diffraction unambiguously demonstrated that crystals of (E)-(R)-4-thujanol form a trimer (monoclinic asymmetric (C2)) unit composed of three independent (E)-(R)-4-thujanol molecules. The trimer is further organized into a chiral P-type supramolecular helix of trimers through a network of intermolecular hydrogen bonds. This study is based on the cheap, easy and eco-responsible kilogram production of (E)-(R)-4-thujanol crystals may open up new opportunities for the flavor, fragrance and pharmaceutical industries. Fibers of (E)-(R)-4-thujanol may also have applications as bio-active fibrous assemblies.
dc.language.isoENen_US
dc.title.enNatural crystalline fibers of (E)-(R)-4-thujanol: green kilogram production from a selected wild thyme. X-ray and NMR characterization of a spiral structure
dc.title.alternativeIndustrial Crops and Productsen_US
dc.typeArticle de revueen_US
dc.identifier.doi10.1016/j.indcrop.2022.115451en_US
dc.subject.halChimie/Matériauxen_US
bordeaux.journalINDUSTRIAL CROPS AND PRODUCTSen_US
bordeaux.volume187en_US
bordeaux.hal.laboratoriesCBMN : Chimie & de Biologie des Membranes & des Nano-objets - UMR 5248en_US
bordeaux.institutionUniversité de Bordeauxen_US
bordeaux.institutionBordeaux INPen_US
bordeaux.institutionCNRSen_US
bordeaux.peerReviewedouien_US
bordeaux.inpressnonen_US
hal.identifierhal-04060349
hal.version1
hal.date.transferred2023-04-06T08:48:21Z
hal.exporttrue
dc.rights.ccPas de Licence CCen_US
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=INDUSTRIAL%20CROPS%20AND%20PRODUCTS&rft.date=2022-11-01&rft.volume=187&rft.eissn=0926-6690&rft.issn=0926-6690&rft.au=MORVAN,%20Estelle&KAUFFMANN,%20Brice&GR%C3%89LARD,%20Axelle&LOQUET,%20Antoine&DIXON,%20Anne-Julie&rft.genre=article


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