3-(6-羟基-2,7,8-三甲基-3,4-二氢-2H-苯并吡喃-2-基)丙酸 | 178167-75-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 3-(6-羟基-2,7,8-三甲基-3,4-二氢-2H-苯并吡喃-2-基)丙酸
• 英文名称: racemic 2,7,8-trimethyl-2-(β-carboxyethyl)-6-hydroxy chroman
• 英文别名: 2,7,8-trimethyl-2-(β-carboxyethyl)-6-hydroxychroman；2,7,8-trimethyl-2-(2-carboxyethyl)-6-hydroxychroman；2,7,8-trimethyl-2-(carboxyethyl)-6-hydroxychroman；γ-carboxyethyl hydroxychroman；γ-CEHC；LLU-α；Gamma-CEHC；3-(6-hydroxy-2,7,8-trimethyl-3,4-dihydrochromen-2-yl)propanoic acid
• CAS: 178167-75-4
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: VMJQLPNCUPGMNQ-UHFFFAOYSA-N

物化性质

• 熔点：
  >125°C (dec.)
• 沸点：
  466.9±45.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)
• 溶解度：
  二氯甲烷（微溶）、乙醇（微溶）、甲醇（微溶）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

γ-CEHC是一种γ-生育酚（HY-N7148）的代谢产物，主要通过尿液排泄，而不是胆汁。在人体尿液中，γ-CEHC通常以共轭形式存在，并主要以葡萄糖醛酸苷的形式出现。

反应信息

• 作为反应物：
  描述：

  3-(6-羟基-2,7,8-三甲基-3,4-二氢-2H-苯并吡喃-2-基)丙酸 在 三氯化铁 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以60%的产率得到racemic 4-methyl-6-(5,6-dimethylbenzochinoyl)-4-hexanolid
  参考文献：
  名称：

  Kantoci, Darko; Wechter, William J.; Murray Jr., E. David, Journal of Pharmacology and Experimental Therapeutics, 1997, vol. 282, # 2, p. 648 - 656

  摘要：

  DOI：

文献信息

• Treatment of mitochondrial diseases
  申请人：Walkinshaw Gail

  公开号：US20050065099A1

  公开（公告）日：2005-03-24

  The invention relates the method of treatment or amelioration of mitochondrial disorders such as Alzheimer's disease, Parkinson's disease, Friedreich's ataxia (FRDA), cerebellar ataxias, Leber's hereditary optic neuropathy (LHON), mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), Myoclonic Epilepsy with Ragged Red Fibers (MERFF), amyotrophic lateral sclerosis (ALS), motor neuron diseases, Huntington's disease, macular degeneration, and epilepsy, with chroman derivatives of Formula I or Formula II as described herein.

  这项发明涉及治疗或改善线粒体疾病，如阿尔茨海默病、帕金森病、弗里德雷希共济失调症（FRDA）、小脑共济失调、勒伯遗传性视神经病变（LHON）、线粒体肌病、脑病、乳酸中毒、中风（MELAS）、带有红色纤维的肌阵挛性癫痫（MERFF）、肌萎缩侧索硬化症（ALS）、运动神经元疾病、亨廷顿病、黄斑变性和癫痫等疾病的治疗方法，所述方法使用本文描述的Formula I或Formula II的类胡萝卜素衍生物。
• Pyruvate derivatives
  申请人：——

  公开号：US20030013656A1

  公开（公告）日：2003-01-16

  Certain known and novel pyruvate derivatives are particularly active in restoring or preserving metabolic integrity in oxidatively competent cells that have been subjected to oxygen deprivation. These pyruvate-derived compounds include, but are not limited to oximes, amides, pyruvate analogues, modified pyruvate analogues, esters of pyruvate (e.g., polyol-pyruvate esters, pyruvate thioesters, glycerol-pyruvate esters and dihydroxyacetone-pyruvate esters). Such pyruvate derivatives (including single tautomers, single stereoisomers and mixtures of tautomers and/or stereoisomers, and the pharmaceutically acceptable salts thereof) are useful in the manufacture of pharmaceutical compositions for treating a number of conditions characterized by oxidative stress.

  某些已知和新颖的丙酮酸衍生物在恢复或保护已经遭受氧气剥夺的氧化能力细胞的代谢完整性方面特别活跃。这些由丙酮酸衍生的化合物包括但不限于肟、酰胺、丙酮酸类似物、改性丙酮酸类似物、丙酮酸酯（例如，聚醇丙酮酸酯、丙酮酸硫酯、甘油丙酮酸酯和二羟基丙酮酸酯）。这些丙酮酸衍生物（包括单重构体、单立体异构体和重构体和/或立体异构体混合物以及其药用可接受的盐）可用于制造用于治疗多种由氧化应激特征的疾病的药物组合物。
• Chroman derivatives for the reduction of inflammation symptoms
  申请人：——

  公开号：US20040097433A1

  公开（公告）日：2004-05-20

  The present invention provides a composition comprising chroman derivatives, for use in the reduction of inflammatory markers associated with inflammation, particularly for the reduction of C-reactive protein (CRP) and for use in the treatment and/or amelioration of symptoms of inflammation.

  本发明提供一种包含香豆素衍生物的组合物，用于减少与炎症相关的炎症标志物，特别是用于减少C-反应蛋白(CRP)，并用于治疗和/或缓解炎症症状。
• Enzymatic Sulfation of Tocopherols and Tocopherol Metabolites by Human Cytosolic Sulfotransferases
  作者：Takuyu HASHIGUCHI、Katsuhisa KUROGI、Yoichi SAKAKIBARA、Masao YAMASAKI、Kazuo NISHIYAMA、Shin YASUDA、Ming-Cheh LIU、Masahito SUIKO

  DOI：10.1271/bbb.110352

  日期：2011.10.23

  Tocopherols are essential micronutrients for mammals widely known as potent lipid-soluble antioxidants that are present in cell membranes. Recent studies have demonstrated that most of the carboxychromanol (CEHC), a tocopherol metabolite, in the plasma exists primarily in sulfate- and glucuronide-conjugated forms. To gain insight into the enzymatic sulfation of tocopherols and their metabolites, a systematic investigation was performed using all 14 known human cytosolic sulfotransferases (SULTs). The results showed that the members of the SULT1 family displayed stronger sulfating activities toward tocopherols and their metabolites. These enzymes showed a substrate preference for γ-tocopherol over α-tocopherol and for γ-CEHC over other CEHCs. Using A549 human lung epithelial cells in a metabolic labeling study, a similar trend in the sulfation of tocopherols and CEHCs was observed. Collectively, the results obtained indicate that SULT-mediated enzymatic sulfation of tocopherols and their metabolites is a significant pathway for regulation of the homeostasis and physiological functions of these important compounds.

  生育酚是哺乳动物必需的微量营养素，被广泛认为是存在于细胞膜中的有效脂溶性抗氧化剂。最近的研究表明，血浆中的大部分羧基苯并二氢吡喃醇 (CEHC)（一种生育酚代谢物）主要以硫酸盐和葡萄糖醛酸结合形式存在。为了深入了解生育酚及其代谢物的酶促硫酸化，使用所有 14 种已知的人类胞质磺基转移酶 (SULT) 进行了系统研究。结果表明，SULT1家族成员对生育酚及其代谢物表现出更强的硫酸化活性。这些酶显示出对 γ-生育酚的底物偏好高于 α-生育酚，对 γ-CEHC 的底物偏好高于其他 CEHC。在代谢标记研究中使用 A549 人肺上皮细胞，观察到生育酚和 CEHC 硫酸化的类似趋势。总的来说，获得的结果表明，SULT 介导的生育酚及其代谢物的酶促硫酸化是调节这些重要化合物的稳态和生理功能的重要途径。
• [EN] NON-TOXIC IRON CHELATORS WITH NEUROPROTECTIVE POTENTIAL<br/>[FR] CHÉLATEURS DE FER NON TOXIQUES À POTENTIEL NEUROPROTECTEUR
  申请人：UNIV SYDNEY

  公开号：WO2017201581A1

  公开（公告）日：2017-11-30

  The present invention relates to new desferrioxamine B-based compounds that may be useful to treat neurodegenerative diseases, to their preparation, and to compositions including the compounds. The present invention also relates to the use of the compounds, as well as compositions including the compounds, in the treatment of neurodegenerative disorders (such as Parkinson's disease).

  本发明涉及一种基于新的去铁胺B的化合物，可能有用于治疗神经退行性疾病，以及其制备和包括该化合物的组合物。本发明还涉及使用该化合物以及包括该化合物的组合物治疗神经退行性疾病（如帕金森病）。