(-)-4,5'-dimethyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol | 35482-50-9

• 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: (-)-4,5'-dimethyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol
• 英文别名: 5-methyl-2-[(6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene-1,3-diol；cannabidiorcinol
• CAS: 35482-50-9
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: GKVOVXWEBSQJPA-LSLKUGRBSA-N

物化性质

• 沸点：
  414.3±45.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)
• 溶解度：
  乙醇中≤30mg/ml；DMSO中≤30mg/ml；二甲基甲酰胺中≤30mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 储存条件：
  -20°C，密闭保存，干燥环境

制备方法与用途

cannabidiorcol（CBDO、CBD-C1、O-1821）是一种大麻二酚的衍生物，其戊基侧链缩短为甲基。它对大麻素受体（CB）的亲和力较低，但能激活瞬时受体电位通道（TRP channel），从而产生抗炎作用。然而，在高浓度下，它还可能促进肿瘤的发生。

反应信息

• 作为产物：
  描述：

  甜橙提取物 在 silver trifluoromethanesulfonate 、 1-fluoro-4-methyl-1,4-diazoniabicyclo<2.2.2>octane ditetrafluoroborate 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 生成 (-)-4,5'-dimethyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol
  参考文献：
  名称：

  [EN] PROCESS FOR THE SYNTHESIS OF CANNABIDIOL AND INTERMEDIATES THEREOF
  [FR] PROCÉDÉ DE SYNTHÈSE DE CANNABIDIOL ET DE SES INTERMÉDIAIRES

  摘要：

  本发明涉及从化合物（B）出发，通过中间体（C）和（D），从（D）和（E）的偶联制备大麻二酚（A）的方法。该发明还涉及在该过程中使用的新化合物（B）、（C）、（D）和（E）以及试剂。更具体地说，本发明提供了以毫克至克或千克为单位生产大麻二酚（A）的方法。

  公开号：

  WO2021181420A1

文献信息

• One-step flow-mediated synthesis of cannabidiol (CBD) and derivatives
  申请人：TRUSTEES OF BOSTON UNIVERSITY

  公开号：US10981850B2

  公开（公告）日：2021-04-20

  Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.

  本文描述了制备大麻素（如大麻二酚（CBD）及其衍生物）的设备和工艺。所述设备和工艺可用于一步法、流动介导合成大麻二酚及其衍生物，与批量工艺相比，总体产量、材料吞吐量和产品纯度均有所提高。
• COMPOSITIONS CONTAINING OMEGA-3 FATTY ACIDS CONCENTRATES, CANNABANOIDS AND L-THEANINE AND USE THEREOF
  申请人：Omax Health

  公开号：US20190336471A1

  公开（公告）日：2019-11-07

  The present disclosure relates to compositions that provide anti-anxiety relief and similar benefits and use thereof. In particular, the disclosure provides compositions containing omega-3 fatty acids concentrates, cannabanoids and L-Theanine, and the synergistic effects of these compositions provides multiple health and wellness benefits. The disclosure further provides the use of these compositions in addressing multiple indications for health and wellness, including but not limited to, sleeplessness, anxiety, pain associated with general inflammation, drug addiction, brain injury, and/or alpha wave brain disorder.
• ONE-STEP FLOW-MEDIATED SYNTHESIS OF CANNABIDIOL (CBD) AND DERIVATIVES
  申请人：TRUSTEES OF BOSTON UNIVERSITY

  公开号：US20210163387A1

  公开（公告）日：2021-06-03

  Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.
• CELLULAR RETINOID BINDING PROTEIN ANTAGONISTS AND USES THEREOF
  申请人：CASE WESTERN RESRVE UNIVERSITY

  公开号：US20210228500A1

  公开（公告）日：2021-07-29

  A method of treating an ocular, inflammatory, immune, and/or metabolic disorder in a subject in need thereof includes administering to the subject a therapeutically effective amount of a compound having a structure of formula (I).
• METHODS AND COMPOSITIONS FOR MODULATING BLOOD-BRAIN BARRIER
  申请人：INSERM (institut National de la Santé et de la Recherche Médicale)

  公开号：US20220117911A1

  公开（公告）日：2022-04-21

  The present invention relates to a method for modulating blood-brain barrier (BBB) in a subject comprising a step of administering said subject with a therapeutically effective amount of a modulator of transient receptor potential vanilloid-2 (TRPV2). For the first time, inventors have shown that TRPV2 is present in endothelial cells of BBB. More particularly, Inventor's results show that cannabidiol (CBD), at extracellular concentrations close to those observed in plasma of patients treated by CBD, and induces proliferation, migration, tubulogenesis and TEER increase in human brain endothelial cells, suggesting TRPV2 as a potent target for modulating the human BBB.