(+)-Cedrol hemihydrate: a natural product derived from drying eastern red cedar (Juniperus virginiana) wood.

IF 0.7 4区化学 Q4 CHEMISTRY, MULTIDISCIPLINARY

Acta Crystallographica Section C Structural Chemistry Pub Date : 2024-02-01 Epub Date: 2024-01-28 DOI:10.1107/S2053229624000780

Bryan C Chakoumakos, Xiaoping Wang

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Abstract

Cedrol-like compounds are of pharmacological interest due to their diverse range of medicinal effects and are used globally in traditional medicines and cosmetics. Many cedrol tautomers are known from molecular studies but few have been studied in crystalline form by X-ray diffraction. Acicular white crystals collected from the wood of eastern red cedar (Juniperus virginiana) are determined to be (+)-cedrol hemihydrate, namely, (1S,2R,5S,7R,8R)-2,6,6,8-tetramethyltricyclo[5.3.1.0^1,5]undecan-8-ol hemihydrate, C₁₅H₂₆O·0.5H₂O, a novel packing of two unique cedrol molecules (Z' = 2) with a single water molecule [space group P2₁2₁2₁; a = 6.1956 (1), b = 14.5363 (1), and c = 30.9294 (4) Å]. The hydrogen bonding forms a one-dimensional spiral chain running along the a axis, following the chirality of the cedrol molecule, through hydrogen-bonding interactions with a right-handed helical configuration in graph-set notation Δ-C₃³(6) > a > c > b. The crystal packing and symmetry are different from crystalline isocedrol due to the different hydrogen-bonding geometry.

Abstract Image

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(+)-Cedrol hemihydrate：一种从干燥的东部红雪松（Juniperus virginiana）木材中提取的天然产品。

香柏木类化合物具有多种药用功效，在全球范围内被广泛用于传统药物和化妆品中，因而具有重要的药理作用。分子研究发现了许多柏木酚同系物，但通过 X 射线衍射法研究结晶形式的柏木酚同系物却寥寥无几。从东部红雪松（Juniperus virginiana）木材中采集的白色针状晶体被确定为 (+)-cedrol 半水合物，即 (1S,2R,5S,7R,8R)-2,6,6,8-四甲基三环[5.3.1.01,5]十一烷-8-醇半水合物，C15H26O-0.5H2O，是由两个独特的鲸蜡醇分子（Z' = 2）与一个水分子[空间群 P212121；a = 6.1956 (1)，b = 14.5363 (1)，c = 30.9294 (4)埃]组成的新颖堆积。由于氢键的几何形状不同，晶体的堆积和对称性也不同于异丙醇晶体。

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来源期刊

Acta Crystallographica Section C Structural Chemistry CHEMISTRY, MULTIDISCIPLINARYCRYSTALLOGRAPH-CRYSTALLOGRAPHY

CiteScore

1.60

自引率

12.50%

发文量

148

期刊介绍： Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.