Δ⁸-tetrahydrocannabino-1-O-carboxypropyl ether

• 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: Δ⁸-tetrahydrocannabino-1-O-carboxypropyl ether
• 英文别名: (6aR-trans)-4-[(6a,7,10,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-yl)oxy]butanoic acid；4-[[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-yl]oxy]butanoic acid
• 化学式: C₂₅H₃₆O₄
• 分子量: 400.558
• InChiKey: OKOFRSLZXREDHW-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  (-)-Δ8-四氢大麻酚	delta-8-tetrahydrocannabinol	5957-75-5	C21H30O2	314.468

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(6aR-trans)-4-[(6a,7,10,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6Hdibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide	78527-68-1	C33H45NO4	519.725
  四氢大麻酚	dronabinol	1972-08-3	C21H30O2	314.468

反应信息

• 作为反应物：
  描述：

  Δ⁸-tetrahydrocannabino-1-O-carboxypropyl ether 、 草酰氯 、 、 对羟基苯乙胺 、 盐酸 、 水 在 草酰氯 、 苯 、 乙醚 、 ice 、 甲醇 、 氯仿 作用下， 以 苯 、 sodium hydroxide 为溶剂， 反应 1.5h， 以gave 738 mg (27%) of (6aR-trans)-4-[(6a,7,10,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6Hdibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide as a pale yellow gum occluding 0.5 mol of water的产率得到(6aR-trans)-4-[(6a,7,10,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6Hdibenzo[b,d]pyran-1-yl)oxy]-N-[2-(4-hydroxyphenyl)ethyl]-butanamide
  参考文献：
  名称：

  Radioimmunoassay for cannabinoids

  摘要：

  本文描述了一种改进的免疫测定法，用于检测大麻素。该免疫测定法的特点是利用抗体、标记为.sup.125 I放射性的抗原、未标记的抗原和阴离子交换树脂分离标记和未标记的抗原。碘化的四氢大麻酚基团通过添加少量抗氧化剂（如叔丁基羟基甲苯）稳定。

  公开号：

  US04438207A1
• 作为产物：
  描述：

  (-)-Δ8-四氢大麻酚 在 sodium hydroxide 、 四乙基氟化铵水合物 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 Δ⁸-tetrahydrocannabino-1-O-carboxypropyl ether
  参考文献：
  名称：

  Time-Resolved Fluoroimmunoassay for Δ⁹-Tetrahydrocannabinol As Applied to Early Discrimination of Cannabis sativa Plants

  摘要：

  In the cultivations of Cannabis, it is important to be able to distinguish fiber-type plants from drug-type plants by an easy observation of their phenotype. This study required the screening of many samples for their cannabinoid content. A simple and highly sensitive time-resolved fluoroimmunological method was developed for the determination of Delta(9)-tetrahydrocannabinol in the leaf extracts. The useful range of the calibration curve was between 10 pg and 25 ng of standard. Matrix effects were minimized by a high dilution of samples.

  DOI：

  10.1021/jf981141b

文献信息

• Tetrahydrocannabinol derivatives, 125I-labeled tetrahydrocannabinol derivatives, immunogens yielding antibodies and radioimmunoassay for detecting cannabinoids
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0027567A1

  公开（公告）日：1981-04-29

  An improved immunoassay for detecting cannabinoids is described. This immunoassay is characterized by utilizing, as reagents, antibody, 125I-radiolabeled antigen, an unlabeled antigen and an anion exchange resin for separation of labeled and unlabeled antigen. The iodinated tetrahydrocannabinol moiety is stabilized by the addition of small quantities of antioxidants such as butylated hydroxytoluene.

  描述了一种用于检测大麻素的改进型免疫测定法。 该免疫测定法的特点是利用抗体、125I-放射性标记抗原、未标记抗原和阴离子交换树脂作为试剂，用于分离标记抗原和未标记抗原。 通过添加少量抗氧化剂（如丁基羟基甲苯）来稳定碘化四氢大麻酚分子。
• US4438207A
  申请人：——

  公开号：US4438207A

  公开（公告）日：1984-03-20
• Time-Resolved Fluoroimmunoassay for Δ⁹-Tetrahydrocannabinol As Applied to Early Discrimination of <i>Cannabis</i> <i>sativa </i>Plants
  作者：Maria A. Bacigalupo、Adriano Ius、Giacomo Meroni、Gianpaolo Grassi、Anna Moschella

  DOI：10.1021/jf981141b

  日期：1999.7.19

  In the cultivations of Cannabis, it is important to be able to distinguish fiber-type plants from drug-type plants by an easy observation of their phenotype. This study required the screening of many samples for their cannabinoid content. A simple and highly sensitive time-resolved fluoroimmunological method was developed for the determination of Delta(9)-tetrahydrocannabinol in the leaf extracts. The useful range of the calibration curve was between 10 pg and 25 ng of standard. Matrix effects were minimized by a high dilution of samples.
• Radioimmunoassay for cannabinoids
  申请人：Hoffmann-La Roche Inc.

  公开号：US04438207A1

  公开（公告）日：1984-03-20

  An improved immunoassay for detecting cannabinoids is described. This immunoassay is characterized by utilizing, as reagents, antibody, .sup.125 I-radiolabeled antigen, an unlabeled antigen and an anion exchange resin for separation of labeled and unlabeled antigen. The iodinated tetrahydrocannabinol moiety is stabilized by the addition of small quantities of antioxidants such as butylated hydroxy toluene.

  本文描述了一种改进的免疫测定法，用于检测大麻素。该免疫测定法的特点是利用抗体、标记为.sup.125 I放射性的抗原、未标记的抗原和阴离子交换树脂分离标记和未标记的抗原。碘化的四氢大麻酚基团通过添加少量抗氧化剂（如叔丁基羟基甲苯）稳定。