4-[(3-氯-5-甲酰基-4,6-二羟基-2-甲基苯甲酰)氧基]-2-羟基-3,6-二甲基苯甲酸甲酯 | 479-16-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 4-[(3-氯-5-甲酰基-4,6-二羟基-2-甲基苯甲酰)氧基]-2-羟基-3,6-二甲基苯甲酸甲酯
• 英文名称: chloroatranorin
• 英文别名: chloratranorin；chloroantranorin；(3-hydroxy-4-methoxycarbonyl-2,5-dimethylphenyl) 5-chloro-3-formyl-2,4-dihydroxy-6-methylbenzoate
• CAS: 479-16-3
• 化学式: C₁₉H₁₇ClO₈
• 分子量: 408.792
• InChiKey: ABZLZZCDSLOCNF-UHFFFAOYSA-N

物化性质

• 熔点：
  208 °C
• 沸点：
  548.2±50.0 °C(Predicted)
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[(3-氯-5-甲酰基-4,6-二羟基-2-甲基苯甲酰)氧基]-2-羟基-3,6-二甲基苯甲酸甲酯 在 溶剂黄146 作用下， 生成 橡苔
  参考文献：
  名称：

  �ber einen chlorhaltigen Flechtenstoff II

  摘要：

  DOI：

  10.1007/bf01518658
• 作为产物：
  描述：

  巴美灵 以 氘代氯仿 为溶剂， 反应 16.0h， 生成 4-[(3-氯-5-甲酰基-4,6-二羟基-2-甲基苯甲酰)氧基]-2-羟基-3,6-二甲基苯甲酸甲酯
  参考文献：
  名称：

  Chemical constituents of the lichen, Candelaria concolor: A complete NMR and chemical degradative investigation

  摘要：

  A detailed chemical and spectroscopic investigation of the terrestrial lichen Candelaria concolor has yielded several lichenic metabolites belonging to the pulvinic acid series, as well as several depside derivatives including pulvinic dilactone (1), vulpinic acid (4) and calycin (5). The chemical transformation of 1 to pulvinic acid (3) is reported for the first time, as is the conversion of atranorin (6) to 5-chloroatranorin (7) and then finally to 5,5'-dichloroatranorin (8) under very mild conditions. Also presented is the complete 1D and 2D NMR assignment for compounds 1, 3, 4, 5 and 8, including partial NMR chemical shift assignments for the unstable depside (7). Previously, these metabolites had only been partially assigned by NMR spectroscopy.

  DOI：

  10.1080/14786410802682536

文献信息

• Tert-butanolysis of lichen depsides
  作者：Siegfried Huneck

  DOI：10.1016/s0031-9422(00)84138-2

  日期：1984.1
• Chromium-Induced Glucose Uptake, Superoxide Anion Production, and Phagocytosis in Cultured Pulmonary Alveolar Macrophages of Weanling Pigs
  作者：Der-Nan Lee、Houng-Ta Yen、Tian-Fuh Shen、Bao-Ji Chen

  DOI：10.1385/bter:77:1:53

  日期：——

  The dose-dependent effects of chromium chloride(CrCl3) and chromium picolinate (CrPic) were evaluated for their glucose uptake, superoxide anion (O-2(-)) production, activity of glucose-6-phosphate dehydrogenase, and phagocytosis of incubated pulmonary alveolar macrophages in medium containing no or 5 x 10(-8)M insulin. Glucose uptake was found to increase in cells treated with 20 mug/L CrCl3. Incubation with 20 mug/L of CrPic enhanced glucose uptake and O-2(-) production in an insulin-dependent manner. However, the inclusion of CrPic to 100 mug/L in the medium absent of insulin also increased O-2(-) production. The activity of glucose-6-phosphate dehydrogenase was not affected by either the addition of Cr or insulin. The phagocytosis of Escherichia coli by macrophages was enhanced significantly (p < 0.05) in medium containing 10-100 g/L CrCl3 or 20-100 mug/L CrPic in the presence of insulin. These results suggest that the addition of 10-20 mug/L CrCl3 enhances directly the cellular activity of macrophages, whereas the effect of CrPic requires the cooperative action of insulin in enhancing their glucose uptake and phagocytosis.
• ELIX J. A.; NORFOLK S., AUSTRAL. J. CHEM. <AJCH-AS>, 1975, 28, NO 5, 1113-1124
  作者：ELIX J. A.、 NORFOLK S.

  DOI：——

  日期：——
• [EN] PROCESS FOR CONVERTING ATRANOL AND ITS DERIVATIVES INTO HYDROSOLUBLE COMPOUNDS<br/>[FR] PROCÉDÉ DE CONVERSION D'ATRANOL ET DE SES DÉRIVÉS EN COMPOSÉS HYDROSOLUBLES
  申请人：UNIV NICE SOPHIA ANTIPOLIS

  公开号：WO2019175171A1

  公开（公告）日：2019-09-19

  The present disclosure relates to a process for converting atranol and/or its derivatives into hydrosoluble compound(s). In particular, the present disclosure relates to a process for converting atranol and/or its derivative(s), said process comprising a step of mixing a composition comprising atranol and/or its derivative(s)with an enzyme belonging to the peroxidase family and a peroxide.The present disclosure also relates to a process for producing an oakmoss extract having less than 100 ppm of atranol and/or its derivative(s).
• Chemical constituents of the lichen, <i>Candelaria concolor</i>: A complete NMR and chemical degradative investigation
  作者：Daniel A. Dias、Sylvia Urban

  DOI：10.1080/14786410802682536

  日期：2009.7.10

  A detailed chemical and spectroscopic investigation of the terrestrial lichen Candelaria concolor has yielded several lichenic metabolites belonging to the pulvinic acid series, as well as several depside derivatives including pulvinic dilactone (1), vulpinic acid (4) and calycin (5). The chemical transformation of 1 to pulvinic acid (3) is reported for the first time, as is the conversion of atranorin (6) to 5-chloroatranorin (7) and then finally to 5,5'-dichloroatranorin (8) under very mild conditions. Also presented is the complete 1D and 2D NMR assignment for compounds 1, 3, 4, 5 and 8, including partial NMR chemical shift assignments for the unstable depside (7). Previously, these metabolites had only been partially assigned by NMR spectroscopy.