cannabigerol monomethyl ether | 29106-17-0

• 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: cannabigerol monomethyl ether
• 英文别名: O-methylcannabigerol；Phenol, 2-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-3-methoxy-5-pentyl-；2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3-methoxy-5-pentylphenol
• CAS: 29106-17-0
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: KASVLYINZPAMNS-QGOAFFKASA-N

物化性质

• 溶解度：
  DMSO：50 mg/mL（151.29 mM；需要超声波）|

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909500000

反应信息

• 作为反应物：
  描述：

  cannabigerol monomethyl ether 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 正己烷 为溶剂， 反应 0.17h， 以65%的产率得到2-(3,7-dimethylocta-1,6-dienyl)-O-methyl-5-pentylresorcinol
  参考文献：
  名称：

  Srebnik, Morris; Lander, Naphtali; Breuer, Aviva, Journal of the Chemical Society. Perkin transactions I, 1984, # 12, p. 2881 - 2886

  摘要：

  DOI：
• 作为产物：
  描述：

  大麻萜酚 在 咪唑 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 cannabigerol monomethyl ether
  参考文献：
  名称：

  O-Methyl Phytocannabinoids: Semi-synthesis, Analysis in Cannabis Flowerheads, and Biological Activity

  摘要：

  摘要：开发了一种选择性单O-甲基化邻苯二酚类植物大麻素的通用协议。半合成的大麻酚酸、大麻二酚和大麻二酚酯（分别为1a-3a）的可用性使得能够在大约40种不同类型的纤维大麻中定量这些次要的植物大麻素。没有任何类型明显积累单O-甲基大麻二酚（2b）或其较低的同系物（3b），而至少有三种类型含有一致数量（≥400mg/kg）的O-甲基大麻酚酸（1b）。与已报道的苯乙基类似物相反，烷基植物大麻素（1b-3b）的O-甲基化不会显著改变对过氧化物酶体增殖物活化受体的活性。

  DOI：

  10.1055/a-0883-5383

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS<br/>[FR] PROCÉDÉS DE PRÉPARATION DE COMPOSÉS HYDROXY-ARYLE ORTHO-ALLYLÉS
  申请人：UNIV MCMASTER

  公开号：WO2021237371A1

  公开（公告）日：2021-12-02

  The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

  本申请描述了一种制备邻烯丙基羟基芳基化合物的方法，例如通过在非质子溶剂中，在氧化铝和铝烷氧化物中选择的铝化合物存在下，将烯丙醇与羟基芳基化合物反应，其中羟基芳基化合物中至少有一个碳原子位于羟基的邻位且未被取代。本申请还包括化合物的化学式（I）。
• Novel CBG Derivatives Can Reduce Inflammation, Pain and Obesity
  作者：Natalya M. Kogan、Yarden Lavi、Louise M. Topping、Richard. O. Williams、Fiona E. McCann、Zhanna Yekhtin、Marc Feldmann、Ruth Gallily、Raphael Mechoulam

  DOI：10.3390/molecules26185601

  日期：——

  Interest in CBG (cannabigerol) has been growing in the past few years, due to its anti-inflammatory properties and other therapeutic benefits. Here we report the synthesis of three new CBG derivatives (HUM-223, HUM-233 and HUM-234) and show them to possess anti-inflammatory and analgesic properties. In addition, unlike CBG, HUM-234 also prevents obesity in mice fed a high-fat diet (HFD). The metabolic state of the treated mice on HFD is significantly better than that of vehicle-treated mice, and their liver slices show significantly less steatosis than untreated HFD or CBG-treated ones from HFD mice. We believe that HUM-223, HUM-233 and HUM-234 have the potential for development as novel drug candidates for the treatment of inflammatory conditions, and in the case of HUM-234, potentially for obesity where there is a huge unmet need.

  近年来，对CBG（cannabigerol）的兴趣不断增长，因为它具有抗炎和其他治疗作用。在这里，我们报道了三种新的CBG衍生物（HUM-223，HUM-233和HUM-234）的合成，并展示它们具有抗炎和镇痛作用。此外，与CBG不同，HUM-234还可以预防高脂饮食（HFD）小鼠的肥胖。治疗后的小鼠代谢状态显著优于接受车辆处理的小鼠，其肝脏切片显示明显较少的脂肪变性，而未经处理的HFD或CBG处理的小鼠则相反。我们相信，HUM-223，HUM-233和HUM-234具有作为治疗炎症疾病的新型药物候选物的潜力，而在HUM-234的情况下，还可能用于肥胖症治疗，这是一个急需解决的问题。
• [EN] PLATINUM COMPLEX ANTI-NEOPLASTIC AGENTS COMPRISING A CANNABINOID LIGAND<br/>[FR] AGENTS ANTINÉOPLASIQUES COMPLEXES DE PLATINE COMPRENANT UN LIGAND CANNABINOÏDE
  申请人：DIVERSE BIOTECH INC

  公开号：WO2021034405A1

  公开（公告）日：2021-02-25

  This disclosure provides platinum complex anti-neoplastic agents that comprise at least one cannabinoid ligand as either a leaving ligand or an axial ligand. After the agent enters the cell, the cannabinoid ligand is released as a cannabinoid, where the cannabinoid can then provide additional therapeutic benefits.

  本发明提供了至少包含一个大麻素配体作为离去配体或轴向配体的铂配合物抗肿瘤剂。当该药剂进入细胞后，大麻素配体将作为大麻素释放出来，大麻素可以提供额外的治疗效益。
• Cannabinoid composition and products including α-tocopherol
  申请人：Constance Therapeutics, Inc.

  公开号：US10238745B2

  公开（公告）日：2019-03-26

  A cannabinoid composition having an excipient including α-tocopherol and at least one isolated cannabinoid having a purity of greater than 80%. The α-tocopherol inhibits oxidation, regulates viscosity of the composition, and improves bioavailability of the cannabinoid. The composition includes a carrier oil mixed with the excipient and cannabinoid. In one embodiment, the at least one cannabinoid is an isolated cannabinoid having a greater than 80% purity, and preferably greater than 90% purity. The at least one cannabinoid is selected from the group consisting of phytocannabinoids, endocannabinoids, synthetic cannabinoids, and combinations thereof. The cannabinoid may be derived from plants other than cannabis sativa, or synthesized from fungi, bacteria, yeast or other synthetic method. Preferably the α-tocopherol comprises at least 10% w/w of the composition.

  一种大麻素组合物，其赋形剂包括α-生育酚和至少一种纯度大于 80% 的分离大麻素。α-生育酚可抑制氧化，调节组合物的粘度，提高大麻素的生物利用度。组合物包括与赋形剂和大麻素混合的载体油。在一个实施方案中，至少一种大麻素是分离出来的大麻素，纯度大于 80%，最好大于 90%。至少一种大麻素选自植物大麻素、内源性大麻素、合成大麻素及其组合组成的组。大麻素可以从大麻以外的植物中提取，也可以从真菌、细菌、酵母或其他合成方法中合成。α-生育酚最好至少占组合物重量的 10%。
• Cannabis oil extracts and compositions
  申请人：CONSTANCE THERAPEUTICS, INC.

  公开号：US10406186B2

  公开（公告）日：2019-09-10

  The present invention provides cannabis oil extracts and compositions thereof, including cannabis oil compositions containing vitamin E, and methods for preparing the extracts and compositions. In some embodiments, the present invention provides a method for preparing a cannabis oil extract comprising eluting cannabinoids from cannabis plant material with a solvent to produce an eluate, filtering the eluate with a filter to produce a filtrate, evaporating the solvent from the filtrate with a distiller to produce a distillate, and purging the distillate under conditions sufficient to remove residual solvent, thereby preparing the extract. In some embodiments, the method further includes mixing a quantity of vitamin E with the extract to produce a cannabis oil composition.

  本发明提供了大麻油提取物及其组合物，包括含有维生素 E 的大麻油组合物，以及制备提取物和组合物的方法。在一些实施方案中，本发明提供了一种制备大麻油提取物的方法，包括用溶剂从大麻植物材料中洗脱大麻素以产生洗脱液，用过滤器过滤洗脱液以产生滤液，用蒸馏器蒸发滤液中的溶剂以产生蒸馏物，在足以除去残留溶剂的条件下净化蒸馏物，从而制备提取物。在某些实施方案中，该方法还包括将一定量的维生素 E 与萃取物混合，制成大麻油组合物。