2,6-bis(4'-hydroxy-3',5'-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-4,8-dione | 41514-36-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 2,6-bis(4'-hydroxy-3',5'-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-4,8-dione
• 英文别名: dehydrosinapinic acid dilactone；sinapic acid dimer；(1S,3aS,4S,6aS)-1,4-bis(4-hydroxy-3,5-dimethoxyphenyl)-1,3a,4,6a-tetrahydrofuro[3,4-c]furan-3,6-dione
• CAS: 41514-36-7；63324-54-9；63427-87-2；65167-29-5
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: SOYZXRMXOYGADU-XAMWDVODSA-N

物化性质

• 沸点：
  726.7±60.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,6-bis(4'-hydroxy-3',5'-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-4,8-dione 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 trans-7-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethoxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid
  参考文献：
  名称：

  胸苷酸的合成

  摘要：

  通过将芥子酸（6）氧化苯酚偶联至双内酯（7），然后进行酸催化的重排，通过两个步骤合成了托马斯二酸（2）。脱苄基化和碱水解后，通过苄基化然后通过LAH还原从硫代二酸二甲酯（9）衍生而来的二醇二苄基醚（15）被选择性氧化，生成胸苷酸（1）。

  DOI：

  10.1016/0040-4020(73)80192-9
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 在 三氯化铁 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以75%的产率得到2,6-bis(4'-hydroxy-3',5'-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-4,8-dione
  参考文献：
  名称：

  Phellinsin A 的立体化学：α-亚芳基-γ-内酯的简明合成

  摘要：

  摘要 以简洁的方式制备了Phellinsin A (1a)，从而阐明了1a 中芳基和羧酸基团的相对立体化学。该合成采用了源自肉桂酸衍生物氧化二聚化的双内酯的选择性单水解。该方法为α-亚芳基-γ-内酯的合成提供了一条实用的途径。

  DOI：

  10.1081/scc-200054845

文献信息

• Hydroxycinnamic Acids as DNA-Cleaving Agents in the Presence of Cu^IIIons: Mechanism, Structure–Activity Relationship, and Biological Implications
  作者：Gui-Juan Fan、Xiao-Ling Jin、Yi-Ping Qian、Qi Wang、Ru-Ting Yang、Fang Dai、Jiang-Jiang Tang、Ya-Jing Shang、Li-Xia Cheng、Jie Yang、Bo Zhou

  DOI：10.1002/chem.200901627

  日期：2009.11.23

  The effectiveness of hydroxycinnamic acids (HCAs), that is, caffeic acid (CaA), chlorogenic acid (ChA), sinapic acid (SA), ferulic acid (FA), 3‐hydroxycinnamic acid (3‐HCA), and 4‐hydroxycinnamic acid (4‐HCA), as pBR322 plasmid DNA‐cleaving agents in the presence of CuII ions was investigated. Compounds bearing o‐hydroxy or 3,5‐dimethoxy groups on phenolic rings (CaA, SA, and ChA) were remarkably more

  羟基肉桂酸（HCA）的有效性，即咖啡酸（CaA），绿原酸（ChA），芥子酸（SA），阿魏酸（FA），3-羟基肉桂酸（3-HCA）和4-羟基肉桂酸酸（4-HCA），作为在Cu II离子存在下的pBR322质粒DNA裂解剂进行了研究。酚环上带有邻羟基或3,5-二甲氧基的化合物（CaA，SA和ChA）比不带有此类基团的化合物更有效地引起DNA损伤。此外，在所检查的HCA中，CaA是最活跃的。通过使用特定的清除剂ROS和Cu I抑制DNA断裂，证实了活性氧（ROS）和Cu I离子参与了DNA损伤。螯合剂。还研究了CaA和Cu II离子之间的相互作用以及乙二胺四乙酸（EDTA），溶剂和pH值对相互作用的影响，以帮助通过UV / Vis光谱分析阐明详细的前氧化机理。根据这些观察结果，建议是由CaA酚酸根阴离子而不是母体分子与Cu II离子作为双齿配体螯合，从而促进分子内电子转移形成相应的CaA半醌自由
• Nishiyama, Atsuko; Eto, Hideo; Terada, Yukimasa, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 8, p. 2845 - 2852
  作者：Nishiyama, Atsuko、Eto, Hideo、Terada, Yukimasa、Iguchi, Masanobu、Yamamura, Shosuke

  DOI：——

  日期：——
• Determination of free diferulic, disinapic and dicoumaric acids in plants and foods
  作者：Jiří Grúz、Jiří Pospíšil、Hana Kozubíková、Tomáš Pospíšil、Karel Doležal、Mirko Bunzel、Miroslav Strnad

  DOI：10.1016/j.foodchem.2014.08.131

  日期：2015.3

  Hydroxycinnamates are common phenolic compounds of plants and plant foods, often found in substantial quantities. Due to their high in vitro antioxidant activity they can easily be oxidized under oxidative conditions. In this study, we found that in vitro oxidation of coumaric, ferulic and sinapic acids resulted mainly in dimeric compounds. We hypothesized that these dimers are present in plants and plant foods not only in their bound form but also as free acids that can be extracted from non-hydrolyzed samples. By applying sensitive UHPLC-MSIMS method, we were able to identify and quantify four free hydroxycinnamic acid dimers for the first time, namely 8-8'-disinapic, 8-5'-diferulic, 8-O-4'-diferulic and 8-3'-dicoumaric acids, in wheat sprouts, Chinese cabbage, millet sprouts, light beer and parsley. Concentrations of dicinnamates in plant tissues ranged from 0.05 to 2.8 mu g g(-1) DW and the monomer:dimer ratio ranged from 2 to 850. (C) 2014 Elsevier Ltd. All rights reserved.
• Formation of thomasidioic acid from dehydrosinapinic acid dilactone under neutral conditions, and a remaining inhibitory activity against peroxynitrite-mediated protein nitration
  作者：Toshio Niwa、Umeyuki Doi、Toshihiko Osawa

  DOI：10.1016/s0960-894x(02)00059-8

  日期：2002.3

  Dehydrosinapinic acid dilactone (1) was converted to thomasidioic acid (3) and (E,E)-2,3-bis(3,5-dimethoxy-4-hydroxybenzylidene)succinic acid (4) via an a,p-unsaturated gamma-lactone type dimer (2) in phosphate buffer (pH 7.4). A study of the reaction mechanism was accomplished by observing the reaction of methyl ester of 2. The lignans (3, 4) were also prevented the peroxynitrite-mediated protein nitration. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Biotransformation of Sinapic Acid Catalyzed by <i>Momordica charantia</i> Peroxidase
  作者：Hai-Li Liu、Xiang Wan、Xue-Feng Huang、Ling-Yi Kong

  DOI：10.1021/jf0628072

  日期：2007.2.1

  Biotransformation of sinapic acid (1) with H2O2/Momordica charantia peroxidase, which exists in the widely used food M. charantia, at pH 5.0, 43 degrees C, in the presence of acetone resulted in six compounds, including four new compounds. Compound 2 was the first isolation of a new unique sinapic acid tetrameric derivate, which is formed by peroxidase catalysis in vitro. Besides 2, three other new sinapic acid dimers, 3-5 have also been isolated. Their structures were established on the basis of spectroscopic data. Compound 5 showed a stronger antioxidative activity than the parent sinapic acid (1). Compounds 4 and 5 significantly inhibited the growth of HL-60 cell at the concentration of 10(-5) mol/L.