2-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-5-pentylbenzene-1,3-diol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-5-pentylbenzene-1,3-diol
• 英文别名: 8,9-dihydrocannabidiol；2-(3-Methyl-6-propan-2-ylcyclohex-2-en-1-yl)-5-pentylbenzene-1,3-diol
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: PCXRACLQFPRCBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-5-pentylbenzene-1,3-diol 在 platinum(IV) oxide 、 氢气 、 溶剂黄146 作用下， 反应 12.0h， 以94%的产率得到2-(2-isopropyl-5-methylcyclohexyl)-5-pentylbenzene-1,3-diol
  参考文献：
  名称：

  [EN] USE OF 8,9-DIHYDROCANNABIDIOL COMPOUNDS
  [FR] UTILISATION DE COMPOSÉS DE 8,9-DIHYDROCANNABIDIOL

  摘要：

  本发明提供了一种治疗或减轻癫痫的方法，包括本文所描述的化合物。

  公开号：

  WO2020185661A1
• 作为产物：
  描述：

  α-水芹烯 、 3,5-二羟基戊苯 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 以71%的产率得到2-(6-isopropyl-3-methylcyclohex-2-en-1-yl)-5-pentylbenzene-1,3-diol
  参考文献：
  名称：

  [EN] USE OF 8,9-DIHYDROCANNABIDIOL COMPOUNDS
  [FR] UTILISATION DE COMPOSÉS DE 8,9-DIHYDROCANNABIDIOL

  摘要：

  本发明提供了一种治疗或减轻癫痫的方法，包括本文所描述的化合物。

  公开号：

  WO2020185661A1

文献信息

• 8,9-Dihydrocannabidiol, an Alternative of Cannabidiol, Its Preparation, Antibacterial and Antioxidant Ability
  作者：Qi Wu、Maoyue Guo、Lianghua Zou、Qiqi Wang、Yongmei Xia

  DOI：10.3390/molecules28010445

  日期：——

  Cannabidiol (CBD) from Cannabis sativa is used in cosmetics in North America due to its antibacterial and antioxidant properties, but has been prohibited in many countries except recently; so, finding a non-intoxicating CBD alternative and elucidating the structure–function relationship of CBD analogues is becoming increasingly relevant. Herein, a set of CBD analogues including 8,9-dihydrocannabidiol (H2CBD) was synthesized, and their antibacterial, bactericidal, and antioxidant activity, as well as their structure–function relationship, were studied. The results present a catalytic selectivity near 100% towards H2CBD with a production yield of 85%. Each CBD analogue presented different antibacterial and antioxidant activity. It is revealed that the phenolic hydroxyl moiety is an essential group for CBD analogues to perform antibacterial and antioxidant activities. Among them, H2CBD presented much stronger antibacterial activity than the assayed popular antibiotics. H2CBD and Compound 4 presented very similar radical scavenging activity and inhibition on lipid oxidation to vitamin C, but better thermostability. Moreover, H2CBD presented lower toxicity to human skin fibroblasts at concentrations up to 64-fold higher than its MIC value (1.25 μg/mL) against S. aureus. Above all, in all property experiments, H2CBD presented extremely similar performance to CBD (p < 0.05), including similar time–kill kinetics curves. This research finds H2CBD to be an alternative for CBD with very high potential in the aspects of antibacterial, bactericidal, and antioxidant activity, as well as lower toxicity to human skin fibroblasts.

  来自大麻（Cannabis sativa）的大麻二酚（CBD）因其抗菌和抗氧化特性在北美被用于化妆品中，但除最近外，在许多国家已被禁止使用；因此，寻找一种无毒的 CBD 替代品并阐明 CBD 类似物的结构-功能关系变得越来越重要。本文合成了一组包括8,9-二氢大麻二酚（H2CBD）在内的CBD类似物，并研究了它们的抗菌、杀菌和抗氧化活性及其结构与功能的关系。研究结果表明，H2CBD 的催化选择性接近 100%，产量为 85%。每种 CBD 类似物都具有不同的抗菌和抗氧化活性。结果表明，酚羟基是 CBD 类似物发挥抗菌和抗氧化活性的重要基团。其中，H2CBD 的抗菌活性远远强于所测定的常用抗生素。H2CBD 和化合物 4 的自由基清除活性和对脂质氧化的抑制作用与维生素 C 非常相似，但热稳定性更好。此外，H2CBD 对人类皮肤成纤维细胞的毒性较低，其浓度比其对金黄色葡萄球菌的 MIC 值（1.25 μg/mL）高出 64 倍。最重要的是，在所有特性实验中，H2CBD 的表现与 CBD 极为相似（p < 0.05），包括相似的时间杀伤动力学曲线。这项研究发现，H2CBD 是 CBD 的替代品，在抗菌、杀菌和抗氧化活性方面具有非常高的潜力，而且对人体皮肤成纤维细胞的毒性较低。
• Method for extracting compositions from plants
  申请人：World Class Extractions, Inc.

  公开号：US10851077B2

  公开（公告）日：2020-12-01

  Methods for extracting and concentrating cannabinoids using ultrasound-enhanced solvent extraction. Freshly harvested cannabis plant materials, which may be selectively chosen plant parts or the entire plant itself, are shredded to a particular particle size. The plant material is then mixed with a solvent to form a slurry, and thereafter subjected to ultrasound to release intracellular contents into the solvent. Filtering steps are then applied to remove biomass, waxes and chlorophyll. Water removal and solvent recovery steps are further applied to ultimately derive an extract having high concentrations of target cannabinoids, and in particular cannabidiol (CBD). The methods may be deployed on-site in batch or continuous flow processes, and may further be utilized to derive other types of materials from plants, such as essential oils.

  使用超声波增强溶剂萃取法提取和浓缩大麻素的方法。新鲜收获的大麻植物材料可以是有选择地选择的植物部分，也可以是整个植物本身，将其切碎至特定粒度。然后将植物材料与溶剂混合形成泥浆，再用超声波将细胞内的成分释放到溶剂中。然后采用过滤步骤去除生物质、蜡质和叶绿素。进一步采用除水和溶剂回收步骤，最终提取出具有高浓度目标大麻素，特别是大麻二酚（CBD）的提取物。这些方法可在批量或连续流工艺中现场使用，也可进一步用于从植物中提取其他类型的材料，如精油。
• Solvent-based extraction methods
  申请人：World Class Extractions Inc.

  公开号：US10946306B1

  公开（公告）日：2021-03-16

  Solvent-based methods for the extraction and concentration of cannabinoids and other target compounds from large-scale harvests of cannabis and hemp crops. Select portions of cannabis or hemp plants are harvested, ground to a desired particle size and ultimately powderized where the powder is mixed with a solvent, preferably ethanol or water, to form a slurry that is subjected to at least two, and preferably five or more separate inverting filter centrifugation steps until cannabinoid extraction is maximized. The filtrate from the first inverting centrifugation step is isolated and purified to derive an extract whereas the powderized filtride is subjected to further centrifugation steps. Fresh solvent is introduced at the last inverting centrifugation step and subsequently used upstream in sequentially-earlier centrifugation steps until ultimately utilized in a first inverting filter centrifugation step.

  从大规模收割的大麻和大麻作物中提取和浓缩大麻素及其他目标化合物的溶剂型方法。收获大麻或大麻植物的精选部分，将其研磨至所需粒度并最终粉末化，粉末与溶剂（最好是乙醇或水）混合以形成浆液，浆液至少要经过两步，最好是五步或更多独立的倒置过滤离心步骤，直到大麻素萃取达到最佳效果。从第一个倒转离心步骤中分离和提纯出的滤液可提取出提取物，而粉末化的滤液则需经过进一步的离心步骤。在最后一个倒置离心步骤中引入新鲜溶剂，随后在依次较早的离心步骤中使用上游溶剂，直至最终在第一个倒置过滤离心步骤中使用。
• BREEDING, PRODUCTION, PROCESSING AND USE OF SPECIALTY CANNABIS
  申请人：Biotech Institute, LLC

  公开号：US20160324091A1

  公开（公告）日：2016-11-10

  The invention provides compositions and methods for the breeding, production, processing and use of specialty cannabis.
• METHOD FOR EXTRACTING COMPOSITIONS FROM PLANTS
  申请人：World Class Extractions, Inc.

  公开号：US20190241536A1

  公开（公告）日：2019-08-08

  Methods for extracting and concentrating cannabinoids using ultrasound-enhanced solvent extraction. Freshly harvested cannabis plant materials, which may be selectively chosen plant parts or the entire plant itself, are shredded to a particular particle size. The plant material is then mixed with a solvent to form a slurry, and thereafter subjected to ultrasound to release intracellular contents into the solvent. Filtering steps are then applied to remove biomass, waxes and chlorophyll. Water removal and solvent recovery steps are further applied to ultimately derive an extract having high concentrations of target cannabinoids, and in particular cannabidiol (CBD). The methods may be deployed on-site in batch or continuous flow processes, and may further be utilized to derive other types of materials from plants, such as essential oils.