6,6,8,9-tetrahydrocannabinol | 62532-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,6,8,9-tetrahydrocannabinol
• 英文别名: 6,6,8,9-THC；3,4,5,6-Tetrahydro-7-hydroxy-2-methyl-5-isopropyl-9-pentyl-2,6-methano-2H-1-benzoxocin；5-Isopropyl-2-methyl-9-pentyl-3,4,5,6-tetrahydro-2h-2,6-methanobenzo[b]oxocin-7-ol；9-methyl-5-pentyl-12-propan-2-yl-8-oxatricyclo[7.3.1.02,7]trideca-2,4,6-trien-3-ol
• CAS: 62532-58-5
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: OEDPJGVWHANUAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-二羟基戊苯 、 α-水芹烯 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.0h， 以74%的产率得到6,6,8,9-tetrahydrocannabinol
  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。
• Methods and compositions for treating cancer
  申请人：Sutter West Bay Hospitals

  公开号：US11344527B2

  公开（公告）日：2022-05-31

  This disclosure provides compositions and method useful for treating cell proliferative disorders including cancer. The disclosure provides cannabidiol derivatives and compositions thereof either alone or in combination with THC or a derivative thereof.

  本公开提供了用于治疗包括癌症在内的细胞增殖性疾病的组合物和方法。本公开提供了大麻二酚衍生物及其单独或与四氢大麻酚或其衍生物结合使用的组合物。
• METHODS AND COMPOSITIONS FOR TREATING CANCER
  申请人：McAllister Sean D.

  公开号：US20100204312A1

  公开（公告）日：2010-08-12

  This disclosure provides compositions and method useful for treating cell proliferative disorders including cancer. The disclosure provides cannabidiol derivatives and compositions thereof either alone or in combination with THC or a derivative thereof.
• Novel Nano-Formulation of Cannabidiol (CBD) and Other Cannabinoids for Treatment of Skin Diseases
  申请人：Milane Michael

  公开号：US20220151952A1

  公开（公告）日：2022-05-19

  Compositions and methods are disclosed directed to nanoformulations of cannabidiol.
• [EN] USE OF 8,9-DIHYDROCANNABIDIOL COMPOUNDS<br/>[FR] UTILISATION DE COMPOSÉS DE 8,9-DIHYDROCANNABIDIOL
  申请人：UNIV CALIFORNIA

  公开号：WO2020185661A1

  公开（公告）日：2020-09-17

  The present invention provides a method of treating or mitigating seizures comprising compounds as described herein.

  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。