1-(3,4-二甲氧基苯基)丙烷-1,2-二醇 | 20133-19-1

• 物质功能分类: 天然产物 - 苯丙素
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3,4-二甲氧基苯基)丙烷-1,2-二醇
• 英文名称: 1-(3,4-dimethoxyphenyl)propane-1,2-diol
• 英文别名: 1',2'-Dihydroxymethylisoeugenol
• CAS: 20133-19-1
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: HGABKKBQQGFTLR-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C
• 沸点：
  368.3±42.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)
• LogP：
  0.120 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  1-(3,4-二甲氧基苯基)丙烷-1,2-二醇 在 sodium hypochlorite 、 N-oxyl-immobilized silica gel 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以81%的产率得到藜芦酸
  参考文献：
  名称：

  The Oxidation of Alcohols inN-Oxyl-Immobilized Silica Gel/Aqueous NaOCl Disperse Systems. A Prominent Access to a Column-Flow System

  摘要：

  在分散体系中，以N-氧杂-吸附或固定化硅胶为分散相，以水合NaOCl为分散介质，成功地进行了醇的氧化反应。在分散体系中，二级醇被氧化成相应的酮，而一级醇则根据其结构和反应条件的不同被氧化成醛和/或羧酸。N-氧杂固定化硅胶可被回收并在不显著影响产物收率的情况下重复使用。还研究了一种新的柱流系统，该系统采用新设计的填充N-氧杂固定化硅胶的柱子来进行醇的氧化反应。

  DOI：

  10.1246/bcsj.77.1745
• 作为产物：
  描述：

  苯甲醇,3,4-二甲氧基-a-[1-(2-甲氧基苯氧基)乙基]- 生成 1-(3,4-二甲氧基苯基)丙烷-1,2-二醇
  参考文献：
  名称：

  GRABKINA, O. A.;BABKIN, V. A.;MEDVEDEVA, S. A.;IVANOVA, S. Z.;PAVLINSKIJ,+, XIMIYA DREVESINY,(1987) N 5, 34-40, 121, 122

  摘要：

  DOI：

文献信息

• Metabolism of Methylisoeugenol in Liver Microsomes of Human, Rat, and Bovine Origin
  作者：Alexander T. Cartus、Karl-Heinz Merz、Dieter Schrenk

  DOI：10.1124/dmd.111.038851

  日期：2011.9

  Methylisoeugenol (1,2-dimethoxy-4-propenylbenzene, 1) is a minor constituent of essential oils, naturally occurring as a mixture of cis/trans isomers. 1 is a U.S. Food and Drug Administration-approved food additive and has been given “Generally Recognized as Safe” status. Previously, metabolism of 1 has been studied in the rat, revealing mainly nontoxic cinnamoyl derivatives as major metabolites. However, data concerning the possible formation of reactive intermediary metabolites are not available to date. In this study, the oxidative metabolism of 1 was studied using liver microsomes of rat [not induced, rat liver microsomes (RLM); Aroclor1254 induced RLM (ARLM)], bovine, and human (pooled from 150 donors) origin. Incubations of these microsomes with 1 provided phase I metabolites that were separated by high-performance liquid chromatography (HPLC) and identified by NMR and UV-visible spectroscopy and/or liquid chromatography-mass spectrometry. Identity was confirmed by comparison with 1H NMR spectra of synthesized reference compounds. Formation of metabolites was quantified by HPLC/UV using dihydromethyleugenol (10) synthesized as the internal standard. From incubations of ARLM with 1, seven metabolites could be detected, with 3′-hydroxymethylisoeugenol (2), isoeugenol and isochavibetol (3 + 4), and 6-hydroxymethylisoeugenol (5) being the main metabolites. Secondary metabolites derived from 1 were identified as the α,β-unsaturated aldehyde 3′-oxomethylisoeugenol (6) and 1′,2′-dihydroxy-dihydromethylisoeugenol (7). We were surprised to find that formation of allylic 6-hydroxymethyleugenol (8) was observed starting at approximately 30 min after the beginning of incubations with ARLM. HLM did not form ring-hydroxylated metabolites but were most active in the formation of 6 and 7. ARLM incubations displayed the highest turnover rate and broadest metabolic pattern, presumably resulting from an increased expression of cytochrome P450 enzymes. In conclusion, we present a virtually complete pattern of nonconjugated microsomal metabolites of 1 comprising reactive metabolites and suggest the formation of reactive intermediates that need more investigation with respect to their possible adverse properties.

  美克尔异香豆烯（1,2-二甲氧基-4-丙烯基苯，1）是精油中的次要成分，自然以顺式/反式异构体的混合物存在。1是美国食品药品管理局批准的食品添加剂，并已被认定为“普遍认为安全”。此前，已经在大鼠中研究了1的代谢，主要发现无毒的肉桂酸衍生物作为主要代谢物。然而，目前尚无关于可能形成反应性中间代谢物的数据。在本研究中，我们使用大鼠（未诱导的大鼠肝微粒体；Aroclor1254诱导的大鼠肝微粒体（ARLM））、牛和人类（来自150名供体的 pooled）肝微粒体研究了1的氧化代谢。将这些微粒体与1共同孵育后，获得了第一相代谢物，这些代谢物通过高效液相色谱（HPLC）分离，并通过核磁共振（NMR）和紫外-可见光谱分析和/或液相色谱-质谱法（LC-MS）进行鉴定。通过与合成的对照化合物的1H NMR光谱进行比较来确认其身份。代谢物的形成通过使用合成的内标二氢美克尔异香豆烯（10）进行HPLC/UV定量。从ARLM与1的孵育中，可以检测到七种代谢物，主要代谢物包括3′-羟甲基美克尔异香豆烯（2）、美克尔异香豆烯及异香豆醇（3 + 4），以及6-羟甲基美克尔异香豆烯（5）。从1衍生的次级代谢物被确定为α,β-不饱和醛3′-氧甲基美克尔异香豆烯（6）和1′,2′-二羟基-二氢美克尔异香豆烯（7）。我们惊讶地发现，观察到烯丙基6-羟甲基美克尔异香豆烯（8）的形成，起始于与ARLM孵育约30分钟后。人类肝微粒体（HLM）未形成环羟基化代谢物，但在6和7的形成方面最为活跃。ARLM的孵育显示出最高的周转率和最广泛的代谢模式，这可能是由于细胞色素P450酶的表达增加。总之，我们呈现了1的几乎完整的非结合微粒体代谢物谱，包含反应性代谢物，并建议形成需要更多研究以了解其潜在不良性质的反应性中间体。
• 10.1007/s10973-024-13569-8
  作者：Grzelczyk, Joanna、Pérez-Sánchez, Horacio、Nelen, Jochem、Carmena-Bargueño, Miguel、Gałązka-Czarnecka, Ilona、Budryn, Grażyna、Hernik, Dawid、Brenna, Elisabetta、Boratyński, Filip

  DOI：10.1007/s10973-024-13569-8

  日期：——

  derivatives and their affinity to bind actin and TOPIIα causing inhibition of their functions were evaluated. The ligand–protein binding assay was carried out by isometric titration calorimetry (ITC), and molecular docking, and the antioxidant potential. The highest chelation activity was shown by 5b: 83.95% (FRAP 18.39 μmol Fe(II) mL−1). High affinity for actin and TOPIIα using ITC and docking was shown

  癌症疾病是最常见的死亡原因之一。重要的是在早期阶段减少癌细胞的增殖，同时限制它们的迁移。需要寻找具有中等抗癌预防活性以长期给药的新化合物。 TOPIIα 和肌动蛋白是在炎症状态下可导致癌症进展和新生细胞迁移的蛋白质。寻找能够全面预防癌症的化合物，与 TOPIIα 和肌动蛋白相互作用至关重要，也是我们的目标。在本研究中，评估了丙烯基苯衍生物的抗氧化特性及其与肌动蛋白和 TOPIIα 结合的亲和力，从而抑制其功能。通过等量滴定量热法（ITC）、分子对接和抗氧化潜力进行配体-蛋白质结合测定。 5b显示最高螯合活性：83.95%（FRAP 18.39 μmol Fe(II) mL -1 ）。使用 ITC 和对接，二醇形式显示出对肌动蛋白和 TOPIIα 的高亲和力。对于肌动蛋白，最佳配体是 2b (ΔH − 51.49 kJ mol −1 ， ΔG − 27.37 kJ mol −1 ) 和 5b
• Synthesis of aromatic aldehydes by laccase-mediator assisted oxidation
  作者：Elke Fritz-Langhals、Brigitte Kunath

  DOI：10.1016/s0040-4039(98)01215-5

  日期：1998.8

  Aromatic aldehydes can be prepared in aqueous medium by oxidation of the corresponding methyl aromatic compounds in the presence of oxygen, the enzyme laccase and catalytic amounts of various N-hydroxy compounds. Allylic alcohols also gave the corresponding aldehydes in good yield. Competing reactions reveal that the N-hydroxy compound is involved in the rate determining step of the reaction; (C) 1998 Elsevier Science Ltd. All rights reserved.
• Citterio, Attilio; Arnoldi, Claudio; Giordano, Claudio, Journal of the Chemical Society. Perkin transactions I, 1983, # 5, p. 891 - 896
  作者：Citterio, Attilio、Arnoldi, Claudio、Giordano, Claudio、Castaldi, Grasiano

  DOI：——

  日期：——
• Kolokolow, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1897, vol. 29, p. 23
  作者：Kolokolow

  DOI：——

  日期：——