methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-propionate | 98760-50-0

• 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: methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-propionate
• 英文别名: α-CEHC methyl ester；α-CEHC-Me；3-(6-hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-propionic acid methyl ester；3-(6-Hydroxy-2,5,7,8-tetramethyl-chroman-2-yl)-propionsaeure-methylester；Methyl 3-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydrochromen-2-yl)propanoate
• CAS: 98760-50-0
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: QBMHKUIWUZLKEX-UHFFFAOYSA-N

物化性质

• 沸点：
  418.5±45.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三甲基氢醌 在 硫酸 、 乙酸酐 、 溶剂黄146 、 zinc(II) chloride 作用下， 生成 methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-propionate
  参考文献：
  名称：

  Weichet et al., Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 1689,1691

  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。
• TREATMENT OF MITOCHONDRIAL DISEASES
  申请人：Ampere Life Sciences, Inc.

  公开号：US20130267538A1

  公开（公告）日：2013-10-10

  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.

  本发明涉及使用式I或式II所描述的色酮衍生物的治疗或改善线粒体疾病的方法，例如阿尔茨海默病、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）、带红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、黄斑退化和癫痫。
• Isolation and Identification of α-CEHC Sulfate in Rat Urine and an Improved Method for the Determination of Conjugated α-CEHC
  作者：Yi-Jen Li、Sheng-Ching Luo、Yi-Jing Lee、Fu-Jung Lin、Chi-Cheng Cheng、Yung-Shung Wein、Yueh-Hsiung Kuo、Ching-jang Huang

  DOI：10.1021/jf802459d

  日期：2008.12.10

  2,5,7,8-Tetramethyl-2-(2'-carboxyethyl)-6-hydroxychroman (alpha-CEHC), the water-soluble metabolite of alpha-tocopherol (alpha-TOH) with a shortened side chain but an intact hydroxychroman structure, has been identified in human urine and are thought to be produced in significant amount at excess intake of alpha-TOH. In previous studies, CEHCs in biological specimens were measured by HPLC, GC-MS or LC-MS, preceded by a hydrolysis procedure using either enzyme or methanolic HCI. In an attempt to analyze alpha-CEHC in rat urine accordingly, we observed that enzyme hydrolysis was relatively inefficient in releasing alpha-CEHC compared to high concentrations of HCI. The HCI releasable alpha-CEHC conjugate was isolated and chemically identified as 6-0-sulfated alpha-CEHC (alpha-CEHC sulfate). Using the synthetic alpha-CEHC sulfate standard, it was found that sulfatase could not hydrolyze to a significant extent. On the other hand, pretreatment with HCI at 60 degrees C in the presence of ascorbate, followed by a one-step ether extraction, not only hydrolyzed the sulfate conjugate completely but also extracted alpha-CEHC with high recovery. The inclusion of ascorbate minimized the conversion of alpha-CEHC to alpha-tocopheronolactone in the HCI pretreatment. A complete procedure for the quantitative analysis of alpha-CEHC including HCI hydrolysis, ether extraction and reverse phase isocratic HPLC-ECD was thus established. In conclusion, alpha-CEHC sulfate was isolated and identified as the HCI-releasable conjugate of alpha-CEHC in rat urine. A rapid and sensitive method with high reproducibility for the determination of free, conjugated and total alpha-CEHC is then established.
• [EN] TREATMENT OF MITOCHONDRIAL DISEASES<br/>[FR] TRAITEMENT DE MALADIES MITOCHONDRIALES
  申请人：GALILEO PHARMACEUTICALS INC

  公开号：WO2005032544A1

  公开（公告）日：2005-04-14

  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.
• Weichet et al., Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 1689,1691
  作者：Weichet et al.

  DOI：——

  日期：——