tetrahydrocannabinol | 809279-99-0

• 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: tetrahydrocannabinol
• 英文别名: (6aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo-[c]chromen-1-ol；Δ⁹-tetrahydrocannabinol；(+)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol；(6aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 809279-99-0
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: CYQFCXCEBYINGO-ZYMOGRSISA-N

物化性质

• 沸点：
  390.4±42.0 °C(Predicted)
• 密度：
  1.015±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tetrahydrocannabinol 在 吡啶 、 sodium hydroxide 、 氰化汞 、 六甲基二硅氮烷 作用下， 以 丙酮 为溶剂， 反应 24.66h， 生成
  参考文献：
  名称：

  O- and C-d-glucosyluronic acid derivatives of Δ1-tetrahydrocannabinol: Synthesis and differential behavior to β-glucuronidase

  摘要：

  DOI：

  10.1016/s0008-6215(00)87152-9
• 作为产物：
  描述：

  Methyl tetrahydrocannabinolate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以78%的产率得到tetrahydrocannabinol
  参考文献：
  名称：

  A biomimetic synthesis of Δ1-tetrahydrocannabinol

  摘要：

  DOI：

  10.1016/s0040-4039(00)87498-5

文献信息

• MIXTURES OF CANNABINOID COMPOUNDS, AND PRODUCTION AND USE THEREOF
  申请人：SYMRISE AG

  公开号：US20150336874A1

  公开（公告）日：2015-11-26

  Specific compositions comprising one or multiple (cannabinoid) compound(s) of formula (A) and/or one or multiple salt(s) thereof are described as well as methods for their manufacture. A compound of formula (A), a salt of formula (A) and a respective composition for use as medicine and for use in a method for the therapeutic treatment of the human or animal body, respectively, are also described. Furthermore, corresponding pharmaceutical formulations, cosmetic preparations and foodstuff and/or gourmet or snack preparations fit for consumption as well as a method for the manufacture of delta-9-tetrahydrocannabinol are described.

  具体包含一个或多个公式（A）的（大麻素）化合物以及一个或多个其盐的组合物的描述，以及它们的制造方法。还描述了公式（A）的化合物，公式（A）的盐以及用作药物的相应组合物以及用于治疗人体或动物体的治疗方法。此外，还描述了相应的制药配方、化妆品制剂、食品和/或美食或零食制剂适合食用，以及一种制造Δ-9-四氢大麻酚的方法。
• [EN] METHOD FOR PURIFYING CANNABINOID COMPOUNDS<br/>[FR] PROCÉDÉ DE PURIFICATION DE COMPOSÉS CANNABINOÏDES
  申请人：SYMRISE AG

  公开号：WO2017194173A1

  公开（公告）日：2017-11-16

  The present invention relates to methods for purifying one or two cannabinoid compounds using simulated moving bed chromatography, wherein the cannabinoid compound(s) is/are obtained in the extract and/or the raffinate with the total amount of isomeric impurities being below detection level. In particular, the present invention relates to methods for the purification of cannabidiol, trans-(-)-delta-9-tetrahydrocannabinol, cannabidivarin, trans-(-)-delta-9-tetrahydrocannabivarin and cannabigerol which have been obtained by enantiopure synthesis.

  本发明涉及使用模拟移动床色谱法纯化一种或两种大麻素化合物的方法，其中大麻素化合物在提取物和/或残渣中获得，异构杂质的总量低于检测水平。具体而言，本发明涉及通过对经过对映纯合成获得的大麻二酚、反式-(-)-Δ9-四氢大麻酚、大麻二氢酚、反式-(-)-Δ9-四氢大麻二氢酚和大麻二醇进行纯化的方法。
• [EN] IMPROVED METHODS FOR CONVERTING CANNABIDIOL INTO DELTA9-TETRAHYDROCANNABINOL UNDER NEAT OR APROTIC REACTION CONDITIONS<br/>[FR] PROCÉDÉS AMÉLIORÉS DE CONVERSION DE CANNABIDIOL EN DELTA9-TÉTRAHYDROCANNABINOL DANS DES CONDITIONS DE RÉACTION PURES OU APROTIQUES
  申请人：CANOPY GROWTH CORP

  公开号：WO2020248061A1

  公开（公告）日：2020-12-17

  Disclosed herein is a method for converting cannabidiol (CBD) into a composition comprising Δ9-tetrahydrocannabinol ( Δ9-THC) and Δ8-tetrahydrocannabinol ( Δ8-THC) in which the composition has a Δ9-ΤΗΟ: Δ8-ΤΗΟ ratio of greater than 1.0:1.0. The method comprises contacting the CBD with a Lewis-acidic heterogeneous reagent under reaction conditions comprising: (i) an aprotic-solvent system; (ii) a reaction temperature that is less than a threshold reaction temperature for the Lewis-acidic heterogeneous reagent and the aprotic-solvent system; and (ill) a reaction time that is less than a threshold reaction time for the Lewis-acidic heterogeneous reagent, the aprotic-solvent system, and the reaction temperature. Methods for converting CBD into a composition comprising Δ9-THC and Δ8-THC in which the composition has a Δ9-THC: Δ8-THC ratio of greater than 1.0:1.0 under neat reaction conditions are also provided.

  本公开了一种将大麻二酚（CBD）转化为含Δ9-四氢大麻酚（Δ9-THC）和Δ8-四氢大麻酚（Δ8-THC）的组合物的方法，其中该组合物的Δ9-THC：Δ8-THC比率大于1.0:1.0。该方法包括将CBD与Lewis酸性异质试剂接触，在反应条件下进行反应，包括：（i）无极性溶剂系统；（ii）反应温度低于Lewis酸性异质试剂和无极性溶剂系统的阈值反应温度；以及（iii）反应时间短于Lewis酸性异质试剂、无极性溶剂系统和反应温度的阈值反应时间。还提供了在无净反应条件下将CBD转化为含Δ9-THC和Δ8-THC的组合物的方法，其中该组合物的Δ9-THC：Δ8-THC比率大于1.0:1.0。
• [EN] IMPROVED METHODS FOR CONVERTING CANNABIDIOL INTO DELTA 8-TETRAHYDROCANNABINOL<br/>[FR] PROCÉDÉS AMÉLIORÉS DE CONVERSION DE CANNABIDIOL EN DELTA 8-TÉTRAHYDROCANNABINOL
  申请人：CANOPY GROWTH CORP

  公开号：WO2020248058A1

  公开（公告）日：2020-12-17

  Disclosed herein a method for converting (cannabidiol) CBD into a composition comprising Δ8-tetrahydrocannabinol (A8-THC) and Δ9-tetrahydrocannabinol (Δ9-THC), in which the composition has a Δ8-THC:Δ9-THC ratio that is greater than 1.0:1.0. The method comprises contacting the CBD with a Lewis-acidic heterogeneous reagent under protic, aprotic, or neat reaction conditions comprising: (i) a reaction temperature that is greater than a threshold reaction temperature for the Lewis-acidic heterogeneous reagent and the solvent system; and (ii) a reaction time that is greater than a threshold reaction time for the Lewis-acidic heterogeneous reagent, the solvent system, and the reaction temperature.

  本文公开了一种将（大麻二酚）CBD转化为包含Δ8-四氢大麻酚（A8-THC）和Δ9-四氢大麻酚（Δ9-THC）的组合物的方法，其中该组合物具有Δ8-THC:Δ9-THC比例大于1.0:1.0。该方法包括将CBD与Lewis酸性异质试剂在具有质子、无质子或整齐反应条件下接触，其中该反应条件包括：（i）大于Lewis酸性异质试剂和溶剂系统的阈值反应温度的反应温度；和（ii）大于Lewis酸性异质试剂、溶剂系统和反应温度的阈值反应时间的反应时间。
• APPARATUS FOR CANNABINOL GENERATION AND METHODS OF USING THE SAME
  申请人：AZDT Holdings, LLC

  公开号：US20210380552A1

  公开（公告）日：2021-12-09

  The present disclosure methods for producing cannabinol from Cannabis compositions. The present disclosure further provides apparatuses for the production of cannabinol from Cannabis compositions.

  本公开揭示了从大麻组分中生产大麻酚的方法。本公开进一步提供了从大麻组分生产大麻酚的装置。