(3R,4R)-ω-carboxy-p-cannabidiol | 63998-82-3

• 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: (3R,4R)-ω-carboxy-p-cannabidiol
• 英文别名: 5-[3,5-dihydroxy-4-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]phenyl]pentanoic acid
• CAS: 63998-82-3
• 化学式: C₂₁H₂₈O₄
• 分子量: 344.451
• InChiKey: PAJJRWUTGNKMFJ-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2E,4E)-methyl 2-carboxy-5-(3,5-dibenzyloxyphenyl)penta-2,4-dienoate 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 对甲苯磺酸 作用下， 以 吡啶 、 乙醚 、 水 、 溶剂黄146 、 乙酸乙酯 、 苯 为溶剂， 反应 27.5h， 生成 (3R,4R)-ω-carboxy-p-cannabidiol
  参考文献：
  名称：

  Crombie, Leslie; Crombie, W. Mary L.; Tuchinda, Patoomratana, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1255 - 1262

  摘要：

  DOI：

文献信息

• 一种大麻二酚半抗原与完全抗原的制备方法及应用
  申请人：郑州左安检测科技有限公司

  公开号：CN115160135B

  公开（公告）日：2023-11-03

  一种大麻二酚半抗原与完全抗原的制备方法及应用，大麻二酚半抗原是由3,5‑二甲氧基苯甲醛与三乙基‑4‑磷化物反应生成（2E，4E）‑5‑（3,5‑二甲氧基苯基）‑2,4‑戊二烯酸乙酯，随后经PdC/H2还原，HBr/HoAc脱甲基和皂化反应得到5‑（3,5‑二羟苯基）戊酸，最后再与(1S,4R)‑1‑甲基‑4‑(1‑甲基乙烯基)‑2‑环己烯‑1‑醇反应得到大麻二酚半抗原；大麻二酚完全抗原由大麻二酚半抗原与载体蛋白偶联得到。本发明制备的抗原呈现出特异性的大麻二酚抗原决定簇，使得筛选出高特异性的大麻二酚单克隆抗体成为可能。产生的抗体特异性高、灵敏度高，对大麻及其衍生物均无明显的交叉反应，可用于建立酶联免疫分析方法和胶体金、荧光快速检测试纸法，实现对样品中大麻二酚的快速检测。
• Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability
  作者：William A. Kinney、Mark E. McDonnell、Hua Marlon Zhong、Chaomin Liu、Lanyi Yang、Wei Ling、Tao Qian、Yu Chen、Zhijie Cai、Dean Petkanas、Douglas E. Brenneman

  DOI：10.1021/acsmedchemlett.6b00009

  日期：2016.4.14

  Cannabidiol is the nonpsychoactive natural component of C. sativa that has been shown to be neuroprotective in multiple animal models. Our interest is to advance a therapeutic candidate for the orphan indication hepatic encephalopathy (HE). HE is a serious neurological disorder that occurs in patients with cirrhosis or liver failure. Although cannabidiol is effective in models of HE, it has limitations in terms of safety and oral bioavailability. Herein, we describe a series of side chain modified resorcinols that were designed for greater hydrophilicity and "drug likeness", while varying hydrogen bond donors, acceptors, architecture, basicity, neutrality, acidity, and polar surface area within the pendent group. Our primary screen evaluated the ability of the test agents to prevent damage to hippocampal neurons induced by ammonium acetate and ethanol at clinically relevant concentrations. Notably, KLS-13019 was 50-fold more potent and >400-fold safer than cannabidiol and exhibited an in vitro profile consistent with improved oral bioavailability.
• CROMBIE, LESLIE;CROMBIE, W. MARY L.;TUCHINDA, PATOOMRATANA, J. CHEM. SOC. PERKIN TRANS.,(1988) N 5, 1255-1262
  作者：CROMBIE, LESLIE、CROMBIE, W. MARY L.、TUCHINDA, PATOOMRATANA

  DOI：——

  日期：——
• METHOD OF PURIFYING CANNABINOIDS FROM YEAST FERMENTATION BROTH
  申请人：Demetrix, Inc.

  公开号：US20210189444A1

  公开（公告）日：2021-06-24

  Provided herein are methods of purifying cannabinoids or cannabinoid derivatives produced using modified host cells and recovering the resulting cannabinoid or cannabinoid derivative preparations. The present methods provide preparations comprising cannabinoids or cannabinoid derivatives having increased purity and amounts of the cannabinoids or cannabinoid derivatives.
• OPTIMIZED CANNABINOID SYNTHASE POLYPEPTIDES
  申请人：Demetrix, Inc.

  公开号：US20220228130A1

  公开（公告）日：2022-07-21

  The present disclosure provides engineered variants of a cannabidiolic acid synthase (CBDAS) polypeptide comprising an amino acid sequence of SEQ ID NO:3 with one or more amino acid substitutions, nucleic acids comprising nucleotide sequences encoding said engineered variants, methods of making modified host cells comprising said nucleic acids, modified host cells expressing said engineered variants, methods of producing cannabinoids or cannabinoid derivatives, and methods of screening engineered variants of the cannabidiolic acid synthase (CBDAS) polypeptide.