(±)-nor-cannabichromene

• 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: (±)-nor-cannabichromene
• 英文别名: Cannabichromen；7-Butyl-2-methyl-2-(4-methylpent-3-enyl)chromen-5-ol；7-butyl-2-methyl-2-(4-methylpent-3-enyl)chromen-5-ol
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: KTPDAZGMXXWSMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (±)-nor-cannabichromene 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (1aS,1a¹R,3aR,8bR,2'S)-nor-cannabicyclyl ibuprofenate
  参考文献：
  名称：

  基于大麻环醇类似物的大麻色烯消旋和绝对立体化学

  摘要：

  Cannabichromene (CBC) 在大麻素中是不寻常的，因为它被描述为来自天然大麻来源的外消旋和缩放化合物。对于这种情况有几种解释，包括容易外消旋化。大麻色烯通过色谱分离，并鉴定出与当地大麻中的CBC 匹配的对映异构体。为了防止外消旋化，将 CBC 转化为大麻酚以进行进一步的立体化学分析。这允许 ( R) 基于相关天然产物的手性数据和由 X 射线晶体学确定的大麻环醇类似物的绝对构型，将绝对立体化学分配给天然 CBC。在实验室中发现 CBC 的外消旋化相当缓慢，但可以推断天然大麻产品的处理做法可以促进这一过程。

  DOI：

  10.1021/acs.joc.1c00451
• 作为产物：
  描述：

  1-(but-1-en-1-yl)-3,5-dimethoxybenzene 在 palladium 10% on activated carbon 、 氢气 、 三溴化硼 、 ethylenediamine Tetraacetic Acid 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 (±)-nor-cannabichromene
  参考文献：
  名称：

  次要大麻素作为皮肤炎症抑制剂：化学合成和生物学评价

  摘要：

  尽管治疗性植物的使用已有数千年的历史，但对大麻多样化生物医学潜力的有意开发直到最近才引起人们的关注。生物活性研究主要集中在大麻二酚（CBD）和四氢大麻酚（THC）上，有关更广泛的大麻组“次要植物大麻素”的信息有限。在此背景下，我们的研究目标是合成含有 3 或 4 个碳原子侧链的次要大麻素，重点是大麻醇 (CBG) 和大麻色烯 (CBC) 类似物。利用已知的创新策略，我们合成了 11 种 C3 和 C4 类似物，其中 5 种是皮肤炎症抑制剂，其中 CBG-C4 酯衍生物成为最有效的化合物。

  DOI：

  10.1021/acs.jnatprod.4c00212

文献信息

• LIPOPHILIC ACTIVE AGENT INFUSED TOBACCO LEAVES AND/OR TOBACCO MATERIALS AND METHODS OF USE THEREOF
  申请人：POVIVA TEA, LLC

  公开号：US20210289832A1

  公开（公告）日：2021-09-23

  Aspects described herein relate to lipophilic active agent infused tobacco leaves and/or tobacco materials and methods of use thereof. More particularly, aspects described herein relate to tobacco leaves and/or tobacco materials infused with lipophilic active agents that provide enhanced bioavailability of the lipophilic active agents in a subject, and that mask unpleasant tastes.
• METHOD FOR SELECTIVE SEPARATION, ISOLATION AND RECOVERY OF CANNABIDIOL AND CANNABIDIOL-LIKE MEROTERPENE ACIDS FROM COMPLEX MATRICES
  申请人：NAHTIGAL Istok

  公开号：US20220127213A1

  公开（公告）日：2022-04-28

  Described is a method of selectively isolating non-rigid structure meroterpenes (for example, cannabidiolic acid) from a complex matrix that may also contain rigid structure meroterpenes (for example, THCa), comprising selectively precipitating the non-rigid structure meroterpenes in the form of a triethylamine salt complex by adding triethylamine; isolating the triethylamine salt complex from the mother liquor; then heating the triethylamine salt complex to vaporize the triethylamine, leaving an isolated neutral non-rigid structure meroterpene. In certain embodiments, the starting product is a cannabis resin that has been solubilized in, for example, d-limonene.
• [EN] STABLE FORMULATIONS OF DRONABINOL<br/>[FR] FORMULATIONS STABLES DE DRONABINOL
  申请人：TRYAGX LABS INC

  公开号：WO2021163023A1

  公开（公告）日：2021-08-19

  Described herein are formulations, methods of manufacturing, and methods of treatment using formulations of cannabinoids that are stable at room temperature for at least about one to two years. In one embodiment, the composition is an oxidatively stable formulation of dronabinol.
• [EN] METHODS FOR IDENTIFICATION, STRATIFICATION, AND TREATMENT OF CNS DISEASES<br/>[FR] MÉTHODES POUR L'IDENTIFICATION, LA STRATIFICATION ET LE TRAITEMENT DE MALADIES DU SYSTÈME NERVEUX CENTRAL
  申请人：[en]DUKE UNIVERSITY

  公开号：WO2022081350A2

  公开（公告）日：2022-04-21

  Described herein are methods for identifying mitochondrial defects using metabolomics and genetic analyses and using this information to stratify patients and to correct for metabolic defects in a precision medicine approach. One embodiment is a method for isolating and analyzing samples containing one or more mitochondrial biomarker metabolites or genetic markers useful for the analysis, identification, stratification or classification, and treatment of metabolic changes associated with a CNS or neuropsychiatric disease in a subject and therapies useful for the treatment thereof. In one aspect, the biomarker metabolites comprise mitochondrial metabolites including acylcarnitines and endocannabinoids and the genetic analyses focus on metabolic enzymes or transport mechanisms.
• [EN] PRODUCTION OF CANNABINOIDS/PHYTOCANNABINOIDS WITH A PLANT EXTRACT<br/>[FR] PRODUCTION DE CANNABINOÏDES/PHYTOCANNABINOÏDES À L'AIDE D'UN EXTRAIT VÉGÉTAL
  申请人：[en]TECHNISCHE UNIVERSITÄT DARMSTADT

  公开号：WO2022101306A1

  公开（公告）日：2022-05-19

  The present invention relates to a process for the production of a compound of Formula (I), wherein the process comprises the step of reacting a plant extract having prenyltransferase activity with a compound of Formula (II) and geranyl pyrophosphate (GPP) having Formula (III) to produce the compound of Formula (I), wherein the plant extract is not a plant extract obtainable from a plant that naturally produces cannabinoids/phytocannabinoids. Accordingly, the present invention relates to a process for the production of a compound of Formula (I), wherein the process comprises the step of reacting a plant extract having prenyltransferase activity with a compound of Formula (II) and geranyl pyrophosphate (GPP) having Formula (III) to produce the compound of Formula (I), wherein the plant extract is not Cannabis sativa plant extract. Further, the present invention relates to the process for the production of a compound of Formula (IV), wherein the process comprises producing a compound of Formula (I) by the process as described herein and converting the compound of Formula (I) to the compound of Formula (IV) in the presence of the tetrahydrocannabinolic acid synthase (THCAS; EC 1.21.3.7). The present invention also relates to a process for the production of a compound of Formula (V) wherein the process comprises producing a compound of Formula (I) by the process as described herein and converting the compound of Formula (I) to a compound of Formula (V) in the presence of the THCAS (EC 1.21.3.7), cannabidiolic acid synthase (CBDAS; EC 1.21.3.8) and/or cannabichromenic acid synthase (CBCAS; EC 1.3.3.-). Further, the present invention relates to a process for the production of a compound of Formula (VI) wherein the process comprises producing a compound of Formula (I) by the process as described herein and converting the compound of Formula (I) to a compound of Formula (VI) in the presence of the CBDAS (EC 1.21.3.8).