coclaurine | 2033-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: coclaurine
• 英文别名: Coclaurin；dl-Coclaurin；dl-coclaurine；Machiline；1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
• CAS: 2033-08-1
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: LVVKXRQZSRUVPY-UHFFFAOYSA-N

物化性质

• 熔点：
  219-220 °C
• 沸点：
  496.9±45.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  61.7
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

(±)-椰油酰胺是一种天然产物，可以在折射艾美球虫中找到。这种成分具有抗氧化活性和心血管保健作用。

反应信息

• 作为反应物：
  描述：

  coclaurine 在 tritium oxide 、 potassium tert-butylate 作用下， 反应 110.0h， 生成 (+/-)-<3',5',8-3H3>coclaurine
  参考文献：
  名称：

  Jain, Sudha; Singh, Meenakshi; Bhakuni, Dewan S, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 1, p. 20 - 24

  摘要：

  DOI：
• 作为产物：
  描述：

  (4-ethoxycarbonyloxy-phenyl)-acetic acid-(4-benzyloxy-3-methoxy-phenethylamide) 在 盐酸 、 乙醇 、 水 、 甲苯 、 铂 、 三氯氧磷 作用下， 生成 coclaurine
  参考文献：
  名称：

  The Synthesis of dl-Coclaurine

  摘要：

  DOI：

  10.1021/ja01146a012

文献信息

• Aromatic ethers and process for producing aromatic ethers
  申请人：——

  公开号：US20040181099A1

  公开（公告）日：2004-09-16

  According to a production process, aromatic ethers are producible by reacting phenols with an oxirane compound with use of an anion exchange resin as a catalyst. According to another production process, aromatic ethers having an alcoholic hydroxyl group are producible by a crystallization-purification step of using a solvent having a solubility parameter ranging from 7.5 to 12.5 for purification by crystallization. Further, according to still another production process, producible are aromatic ethers having an alcoholic hydroxyl group, wherein the content of a metal in the aromatic ethers is less than 100 ppm by mass, and the content of a halogen element in the aromatic ethers is less than 100 ppm by mass.

  根据一个生产过程，芳香醚可通过将酚与环氧化合物反应，并使用阴离子交换树脂作为催化剂来生产。根据另一个生产过程，具有醇羟基的芳香醚可通过结晶纯化步骤，使用溶剂进行结晶纯化，其溶解度参数范围为7.5至12.5进行生产。此外，根据另一个生产过程，可生产具有醇羟基的芳香醚，其中芳香醚中金属的含量小于100ppm，卤素元素的含量小于100ppm。
• Effect of Isoquinoline Alkaloids of Different Structural Types on Antiplatelet Aggregation<i>in Vitro</i>
  作者：Yi-Chen Chia、Fang-Rong Chang、Chin-Chung Wu、Che-Ming Teng、Keh-Shaw Chen、Yang-Chang Wu

  DOI：10.1055/s-2006-947196

  日期：2006.10

  Forty-one isoquinoline alkaloids were tested for antiplatelet aggregation effects. Among them, (-)-discretamine (6), protopine (7), ochotensimine (18), O-methylarmepavinemethine (23), lindoldhamine (25), isotetrandrine (26), thalicarpine (27), papaverine (28), and D-(+)-N-norarmepavine (32) exhibited significant inhibitory activity towards adenosine 5′-diphosphate (ADP)-, arachidonic acid (AA)-, collagen-, and/or platelet-activating factor (PAF)-induced platelet aggregation. The results are discussed on the basis of structure-activity relationships.

  测试了41种异喹啉生物碱的抗血小板聚集效果。其中，(-)-discretamine (6)、protopine (7)、ochotensimine (18)、O-methylarmepavinemethine (23)、lindoldhamine (25)、isotetrandrine (26)、thalicarpine (27)、papaverine (28)和D-(+)-N-norarmepavine (32)对腺苷5′-二磷酸（ADP）、花生四烯酸（AA）、胶原蛋白和/或血小板激活因子（PAF）诱导的血小板聚集表现出显著的抑制活性。结果的讨论基于结构-活性关系进行。
• Dehatrine, an antimalarial bisbenzylisoquinoline alkaloid from the indonesian medicinal plant Beilschmiedia madang, isolated as a mixture of two rotational isomers.
  作者：Isao KITAGAWA、Kazuyuki MINAGAWA、Ru-song ZHANG、Kazuyuki HORI、Mitsunobu DOI、Masatoshi INOUE、Toshimasa ISHIDA、Masatsugu KIMURA、Tahan UJI、Hirotaka SHIBUYA

  DOI：10.1248/cpb.41.997

  日期：——

  madang BL. a bisbenzylisoquinoline alkaloid was obtained as the major antimalarial principle. The physicochemical properties of the alkaloid were consistent with the proposed structure of dehatrine. However, the alkaloid isolated by us was shown to be a mixture of two rotational isomers. The X-ray crystallographic analysis of 1 has shown that two rotamers are incorporated in a single crystal in 1:1 ratio

  通过生物分析指导分离印度尼西亚药用植物马齿BLBilschmiedia madang BL的化学成分。获得了双苄基异喹啉生物碱作为主要的抗疟原药。该生物碱的理化性质与拟定的脱hatrine结构一致。然而，我们分离出的生物碱显示为两种旋转异构体的混合物。1的X射线晶体学分析表明，两个旋转异构体以1：1的比例掺入单晶中。通过广泛使用2D（COSY和COLOC）技术，将1的复杂NMR光谱定义为两种旋转异构体的混合物。已显示出Dehatrine具有与奎宁相似的活性，可显着抑制培养的恶性疟原虫K1菌株（对胆碱有抵抗力）的生长。
• [EN] CONSTRUCTS AND METHODS FOR BIOSYNTHESIS OF GALANTHAMINE<br/>[FR] CONSTRUCTIONS ET PROCÉDÉS POUR LA BIOSYNTHÈSE DE LA GALANTHAMINE
  申请人：DONALD DANFORTH PLANT SCI CT

  公开号：WO2015196100A1

  公开（公告）日：2015-12-23

  The present disclosure relates generally to the identification of enzymes within the Amaryllidaceae alkaloid biosynthetic pathway as well as to engineering transgenic organisms for the production of galanthamine and/or hemanthamine and/or lycorine. Disclosed herein is the isolation and characterization of cDNAs and encoded norbelladine 4'-0-methyltransferase, CYP96T1-3, and norbelladine synthase/reductase involved in the biosynthesis of galanthamine and haemanthamine. The invention relates to a transgenic plant, comprising within its genome, and expressing, a heterologous nucleotide sequence coding for a class I O-methyltransferase, wherein the O-methyltransferase is norbelladine 4'-0-methyltransferase. In one embodiment, the norbelladine 4'-0-methyltransferase is selected from among NpN40MT1, NpN40MT2, NpN40MT3, NpN40MT4, and NpN40MT5. The invention further contemplates a method of making a transgenic plant.

  本公开涉及总体上识别阿马里利达斯碱生物合成途径中的酶，以及为生产迎春碱和/或血红碱和/或石蒜碱而工程化转基因生物。本公开揭示了所述cDNA的分离和表征，以及编码的norbelladine 4'-0-甲基转移酶、CYP96T1-3和norbelladine合成酶/还原酶，这些酶参与了迎春碱和血红碱的生物合成。该发明涉及一种转基因植物，其基因组中包含并表达了编码I类O-甲基转移酶的异源核苷酸序列，其中O-甲基转移酶是norbelladine 4'-0-甲基转移酶。在一个实施例中，norbelladine 4'-0-甲基转移酶从NpN40MT1、NpN40MT2、NpN40MT3、NpN40MT4和NpN40MT5中选择。该发明进一步考虑了一种制备转基因植物的方法。
• Process for production of vinyl chloride polymer
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0172427A2

  公开（公告）日：1986-02-26

  This process is a process for production of a vinyl chloride polymer by suspension polymerization or emulsion polymerization of vinyl chloride monomer or a mixture of vinyl chloride monomer with a vinyl monomer copolymerizable with said vinyl chloride monomer in an aqueous medium, characterized in that the polymerization is carried out in a polymerizer, the inner wall surface and portions of the auxiliary equipment thereof which may come into contact with the monomer during polymerization being previously coated with a scaling preventive comprising at least one selected from dyes, pigments and aromatic or heterocyclic compounds having at least 5 conjugated π bonds, while controlling the chloride ion concentration in the reaction mixture to not higher than 100 ppm. According to said process, scaling onto the inner wall surface of a polymerizer, etc. during polymerization can be prevented effectively and surely.

  该工艺是通过氯乙烯单体或氯乙烯单体与可与所述氯乙烯单体共聚的乙烯基单体混合物在水介质中进行悬浮聚合或乳液聚合来生产氯乙烯聚合物的工艺，其特征在于聚合是在聚合器中进行的、内壁表面及其辅助设备中可能在聚合过程中与单体接触的部分事先涂上一层防垢剂，该防垢剂至少包括一种选自染料、颜料和至少有 5 个共轭 π 键的芳香族或杂环化合物的防垢剂，同时控制反应混合物中的氯离子浓度不高于 100 ppm。根据上述工艺，可有效、可靠地防止聚合过程中聚合器等内壁表面结垢。