(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.

( E )-( R ) -4 -Thujanol 存在于百里香精油中，是食品、化妆品和药物应用的重要芳香成分。迄今为止，由于其在百里香或马郁兰等经典芳香植物中的含量较低，其提取仍具有挑战性。尽管这种分子是合成可用的，但由于非常耗时且昂贵的化学过程，没有工业规模的生产。我们在这里首次报道了一种新的生态负责任的方法来生产公斤级的 ( E )-( R ) -4 -thujanol 晶体。这一新的里程碑基于 2 个基础研究空白：i) 选择野生百里香 ( Thymus vulgaris) 因其高含量的 ( E )-( R ) -4 -thujanol 及其在法国普罗旺斯山丘上的精心采摘和 ii) 蒸汽蒸馏产生的有机芳香油，由于空气中有利的两亲性分配而自发聚集-水界面。气相色谱显示由 ( E )-( R ) -4 -thujanol (76%)、百里酚 (5%)、β-月桂烯 (2.8%) 和其他少量单萜组成的组合物。经历升华/结晶循环的白色聚集体导致积累由 ( E )-( R ) -4 -thujanol (98%) 制成的半透明纤维。X-射线衍射清楚地表明，( E )-( R ) -4-thujanol 的晶体形成了由三个独立的( E )-( R ) -4 - thujanol分子组成的三聚体（单斜不对称( C2 ₎）单元。三聚体通过分子间氢键网络进一步组织成三聚体的手性 P 型超分子螺旋。这项研究基于廉价、简单且对生态负责的公斤生产(E)-(R)-4- thujanol 晶体，可能为香精、香料和制药行业开辟新的机遇。( E )-( R )- 4纤维-thujanol 也可用作生物活性纤维组件。