5,5'-dicapsaicin | 134386-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5'-dicapsaicin
• 英文别名: (E)-N-[[4-hydroxy-3-[2-hydroxy-3-methoxy-5-[[[(E)-8-methylnon-6-enoyl]amino]methyl]phenyl]-5-methoxyphenyl]methyl]-8-methylnon-6-enamide
• CAS: 134386-10-0
• 化学式: C₃₆H₅₂N₂O₆
• 分子量: 608.819
• InChiKey: AVNIVUOORMWORM-JOBJLJCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

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
  辣椒碱	capsaicin	404-86-4	C18H27NO3	305.417

反应信息

• 作为反应物：
  描述：

  壬酰氯 、 5,5'-dicapsaicin 在 sodium hydroxide 作用下， 反应 0.5h， 生成
  参考文献：
  名称：

  由 P450 酶代谢辣椒素类香草素环产生的反应性中间体

  摘要：

  本研究表征了细胞色素 P450 和过氧化物酶对辣椒素代谢产生的亲电子和自由基产物。多种谷胱甘肽和 β-巯基乙醇结合物（又名，加合物），来源于捕获辣椒素的醌甲基化物和醌中间体、其类似物壬烯酰胺及其 O-去甲基化和芳香族羟基化代谢物，由人肝微粒体和个体重组人P450 酶。还表征了源自辣椒素烷基末端伴随脱氢的缀合物。对辣椒素类香草素环的 4-OH 取代基的修饰在很大程度上阻止了亲电子中间体的形成，这与各种共轭物的结构和形成机制一致。5,5'-双辣椒素，推测由自由基中间体的双分子偶联引起的也被表征。最后，分析肝谷胱甘肽结合物和尿ñ从与辣椒素给药的小鼠乙酰半胱氨酸缀合物证实O型脱甲基化醌甲基化物和5-OH-辣椒素的谷胱甘肽缀合物的形成体内。这些数据表明，辣椒素和结构相似的类似物被某些 P450 酶转化为反应性中间体，这可能部分解释了与辣椒素在不同细胞和/或器官系统中的细胞毒性、促癌和化学保护作用相关的相互矛盾的报告。

  DOI：

  10.1021/tx300366k
• 作为产物：
  描述：

  辣椒碱 在 双氧水 、 horseradish peroxidase 作用下， 以 aq. buffer 为溶剂， 反应 0.17h， 生成 5,5'-dicapsaicin
  参考文献：
  名称：

  由 P450 酶代谢辣椒素类香草素环产生的反应性中间体

  摘要：

  本研究表征了细胞色素 P450 和过氧化物酶对辣椒素代谢产生的亲电子和自由基产物。多种谷胱甘肽和 β-巯基乙醇结合物（又名，加合物），来源于捕获辣椒素的醌甲基化物和醌中间体、其类似物壬烯酰胺及其 O-去甲基化和芳香族羟基化代谢物，由人肝微粒体和个体重组人P450 酶。还表征了源自辣椒素烷基末端伴随脱氢的缀合物。对辣椒素类香草素环的 4-OH 取代基的修饰在很大程度上阻止了亲电子中间体的形成，这与各种共轭物的结构和形成机制一致。5,5'-双辣椒素，推测由自由基中间体的双分子偶联引起的也被表征。最后，分析肝谷胱甘肽结合物和尿ñ从与辣椒素给药的小鼠乙酰半胱氨酸缀合物证实O型脱甲基化醌甲基化物和5-OH-辣椒素的谷胱甘肽缀合物的形成体内。这些数据表明，辣椒素和结构相似的类似物被某些 P450 酶转化为反应性中间体，这可能部分解释了与辣椒素在不同细胞和/或器官系统中的细胞毒性、促癌和化学保护作用相关的相互矛盾的报告。

  DOI：

  10.1021/tx300366k

文献信息

• Stable aqueous capsaicin injectable formulations and medical uses thereof
  申请人：Centrexion Therapeutics Corporation

  公开号：US10772853B2

  公开（公告）日：2020-09-15

  The invention provides stable, aqueous capsaicin injectable formulations, a unit dose containing such injectable formulations, medical kits, and methods for using such injectable formulations and unit doses to treat patients suffering from pain, such as osteoarthritic knee pain. The stable, aqueous capsaicin injectable formulations may contain, for example, capsaicin, a solubilizing agent (e.g., a polyethylene glycol ester of a (C15-C25) hydroxyalkanoic acid), an antioxidant, and water.

  本发明提供了稳定的辣椒素水溶液可注射制剂、含有这种可注射制剂的单位剂量、医疗包以及使用这种可注射制剂和单位剂量治疗疼痛（如膝关节骨关节炎疼痛）患者的方法。稳定的水性辣椒素可注射制剂可包含，例如，辣椒素、增溶剂（例如，(C15-C25)羟基烷酸的聚乙二醇酯）、抗氧化剂和水。
• Methods and compositions for treatment of pain using capsaicin
  申请人：Centrexion Therapeutics Corporation

  公开号：US11026903B2

  公开（公告）日：2021-06-08

  The invention provides methods and compositions for treatment of pain, such as joint pain, using capsaicin in a procedure that attenuates transient burning sensation experienced by patients due to capsaicin administration. The methods desirably provide relief from joint pain, such as osteoarthritic knee joint pain, for an extended duration, such as at least about 3 months, 6 months, 9 months, or 1 year. To attenuate the adverse side effect of a transient burning sensation caused by capsaicin-induced neuronal excitation, the methods utilize a cooling article, such as a material wrap cooled via a circulating fluid, to reduce the temperature of tissue to be exposed to capsaicin to within a certain range for certain durations of time, optionally in combination with administering a local anesthetic agent, resulting in the substantial reduction or even elimination of transient burning sensation caused by capsaicin.

  本发明提供了使用辣椒素治疗疼痛（如关节疼痛）的方法和组合物，其治疗过程可减轻患者因服用辣椒素而产生的短暂灼烧感。这些方法最好能在较长时间内缓解关节疼痛，例如骨关节炎膝关节疼痛，例如至少约3个月、6个月、9个月或1年。为了减轻由辣椒素诱导的神经元兴奋引起的瞬时烧灼感的不良副作用，这些方法利用冷却物品，例如通过循环流体冷却的材料包裹，将暴露于辣椒素的组织的温度降低到一定范围内，持续一定的时间，可选地与施用局部麻醉剂相结合，从而大大减轻甚至消除由辣椒素引起的瞬时烧灼感。
• Tateba, Hideki; Mihara, Satoru, Agricultural and Biological Chemistry, 1991, vol. 55, # 3, p. 873 - 874
  作者：Tateba, Hideki、Mihara, Satoru

  DOI：——

  日期：——
• Specific Synthesis of 5,5‘-Dicapsaicin by Cell Suspension Cultures of <i>Capsicum</i> <i>annuum</i> Var. <i>annuum</i> (Chili Jalapeño Chigol) and Their Soluble and NaCl-Extracted Cell Wall Protein Fractions
  作者：Víctor M. Martínez-Juárez、Neftali Ochoa-Alejo、Edmundo Lozoya-Gloria、María L. Villarreal-Ortega、Armando Ariza-Castolo、Fernando J. Esparza-García、Graciano Calva-Calva

  DOI：10.1021/jf035214p

  日期：2004.2.1

  HPLC-UV, H-1 NMR, C-13 NMR, and H-1-H-1 COSY analyses revealed that exogenous capsaicin was specifically converted into 5,5'-dicapsaicin by both cell suspension cultures of Capsicum annuum var. annuum (chili Jalapeno chigol) and their soluble and NaCl-extracted cell wall protein fractions under oxidative conditions. In cell suspension cultures 5,5'-dicapsaicin was found only in biomass of capsaicin-fed cultures. This compound has not been detected before either in fresh fruits or in in vitro cultures of Capsicum. The transformation of capsaicin by different protein fractions revealed that most of the enzymatic activity was located in the NaCl-extracted, or ionic cell wall bound, protein, and that it was strictly dependent on H2O2. These results might in part explain some previously described features of capsaicin production by in vitro cultures of Capsicum. The implications of the results regarding the catabolism of capsaicinoids are discussed.
• 5,5‘-Dicapsaicin, 4‘-<i>O</i>-5-Dicapsaicin Ether, and Dehydrogenation Polymers with High Molecular Weights Are the Main Products of the Oxidation of Capsaicin by Peroxidase from Hot Pepper
  作者：María A. Bernal、A. Ros Barceló

  DOI：10.1021/jf950826y

  日期：1996.1.1

  The nature of the products of capsaicin oxidation by hot pepper peroxidase was studied by gel permeation chromatography. Three main types of oxidation products were identified. Peak 1, with an average molecular weight of 603 +/- 12 and corresponding to dimers of capsaicin, was resolved by gas chromatography-mass spectrometry into the dimers 5,5'-dicapsaicin (1a) and 4'-O-5-dicapsaicin ether (1b). Peak 2 appears to be a polymeric product with a molecular weight of 4500 and probably corresponds to polymeric products with a mean degree of 15. Capsaicin-protein copolymers (peak 3) also appear to be products of capsaicin oxidation, probably arising from protein and capsaicin copolymerization. These results suggest that Capsicum peroxidase oxidizes capsaicin to yield 5,5'-dicapsaicin and 4'-O-5-dicapsaicin ether, together a mixture of highly polymerized dehydrogenation products, all of them therefore of a lignin-like nature.