2,4,2′,4′-tetrahydroxychalcone | 25972-30-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,4,2′,4′-tetrahydroxychalcone
• 英文别名: 2',4',2'',4''-tetrahydroxychalcone；2,4,2',4'-tetrahydroxychalcone；2',4,4',6-Tetrahydroxychalcone；1,3-bis(2,4-dihydroxyphenyl)prop-2-en-1-one
• CAS: 25972-30-9
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: ZWTDXYUDJYDHJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4,2′,4′-tetrahydroxychalcone 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以420 mg的产率得到[4-[3-(2,4-Diacetyloxyphenyl)prop-2-enoyl]-3-hydroxyphenyl] acetate
  参考文献：
  名称：

  Kuwanons I和J和Brosimones A和B的对映仿生全合成。

  摘要：

  异戊二烯类黄酮Diels-Alder天然产物（-）-kuwanon I，（+）-kuwanon J，（-）-溴亚砜A和（-）-溴亚砜B的首个对映选择性全合成是基于一种基于简洁的综合策略。合成的关键元素包括由手性配体/硼路易斯酸介导的生物合成启发的不对称Diels-Alder环加成反应，以及涉及区域选择性Schenck烯反应，还原和脱水的过程，以实现仿生脱氢反应，从而产生所需的仿生氢。二烯前体。此外，非凡的串联分子间/分子间不对称Diels-Alder环加成反应过程被用于合成（-）-溴亚砜A。

  DOI：

  10.1002/anie.201404499
• 作为产物：
  描述：

  1-[2-羟基-4-(甲氧基甲氧基)苯基]乙酮 在 盐酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 45.0h， 生成 2,4,2′,4′-tetrahydroxychalcone
  参考文献：
  名称：

  Kuwanons I和J和Brosimones A和B的对映仿生全合成。

  摘要：

  异戊二烯类黄酮Diels-Alder天然产物（-）-kuwanon I，（+）-kuwanon J，（-）-溴亚砜A和（-）-溴亚砜B的首个对映选择性全合成是基于一种基于简洁的综合策略。合成的关键元素包括由手性配体/硼路易斯酸介导的生物合成启发的不对称Diels-Alder环加成反应，以及涉及区域选择性Schenck烯反应，还原和脱水的过程，以实现仿生脱氢反应，从而产生所需的仿生氢。二烯前体。此外，非凡的串联分子间/分子间不对称Diels-Alder环加成反应过程被用于合成（-）-溴亚砜A。

  DOI：

  10.1002/anie.201404499

文献信息

• METHOD AND SYSTEM FOR EFFECTING CHANGES IN PIGMENTED TISSUE
  申请人：Moazed Kambiz Thomas

  公开号：US20110280909A1

  公开（公告）日：2011-11-17

  Methods and systems are described for a rapid and sustainable change in the pigment melanin content of melanocytes of the iris stroma, thereby to change the color of the eye. Also described are nanoparticle compositions for lightening the pigmented tissues or treating a pigmented tissue related disease.

  本文描述了一种快速和可持续改变虹膜基质黑素细胞黑色素含量的方法和系统，从而改变眼睛的颜色。还描述了用于淡化色素组织或治疗色素组织相关疾病的纳米颗粒组合物。
• Method and system for effecting changes in pigmented tissue
  申请人：Moazed Kambiz Thomas

  公开号：US20120207809A1

  公开（公告）日：2012-08-16

  Methods and systems are described for a rapid and sustainable change in the pigment melanin content of melanocytes of the iris stroma, thereby to change the color of the eye. Also described are compositions for lightening or darkening the pigmented tissues or treating a pigmented tissue disease.

  本文描述了一种快速和可持续改变虹膜基质黑素细胞中黑色素含量的方法和系统，从而改变眼睛的颜色。还描述了用于使色素组织变浅或变深或治疗色素组织疾病的组合物。
• Aspergillus niger catalyzes the synthesis of flavonoids from chalcones
  作者：Julio Alarcón、Joel Alderete、Carlos Escobar、Ramiro Araya、Carlos L. Cespedes

  DOI：10.3109/10242422.2013.813489

  日期：2013.8

  Flavonoids, which have many biological activities and have been widely used in nature, can be artificially synthesized. However, regioselective cyclization of chalcones is difficult by chemical methods. In this study, we demonstrated that Aspergillus niger is capable of cyclizing chalcones to flavanones, affording a mimic of plant biosynthetic processes. Chalcones 1-6 were biotransformated to the modified chalcones 8-14 and to the flavanones 15-27. The biotransformation showed that enzymatic cyclization and demethylation occurred during the first days of biotransformation; in contrast, hydroxylation is a later process. With a longer culturing time, it is possible to obtain more hydroxylated flavanones with excellent yields.
• Preparation of tyrosinase inhibitors and antibrowning agents using green technology
  作者：Xue Dong、Yinan Zhang、Jia-Liang He、Shuang Zhang、Mao-Mao Zeng、Jie Chen、Zong-Ping Zheng

  DOI：10.1016/j.foodchem.2015.11.007

  日期：2016.4

  Chalcones and their derivatives have attracted great interests in recent years for their comprehensive biological activities. In this study, 2,4,2',4'-tetrahydroxychalcone and its two derivatives, 1,3,5-tris-(2,4-dihydroxy-phenyl)pentane-1,5-dione (new compound) and 7,2',4'-trihydroxyflavanone, were synthesized through one-pot green procedure catalyzed by boric acid in polyethylene glycol 400. Their structures were identified by ESI-MS and NMR spectral. Tyrosinase inhibitory activity and antibrowning test results showed that compounds 1-3 exhibited strong tyrosinase inhibitory activities and significant antibrowning effects on the fresh-cut lotus root slices at room temperature in 48 h. Among them, 0.01% 1,3,5-tris-(2,4-dihydroxy-phenyl)pentane-1,5-dione combined with 0.5% VC showed the best antibrowning ability. In brief, this study offers a protocol for one-pot green synthesis of high efficiency tyrosinase inhibitors which may be suitable as antibrowning agents for fresh-cut vegetables. More important, this study developed a new type of 1,5-dione derivative which may serve as new lead structures for novel tyrosinase inhibitors discovery.
• Electron Transfer-Initiated Diels−Alder Cycloadditions of 2′-Hydroxychalcones
  作者：Huan Cong、Dustin Ledbetter、Gerard T. Rowe、John P. Caradonna、John A. Porco

  DOI：10.1021/ja803094u

  日期：2008.7.1

  An efficient approach to cyclohexenyl chalcones employing highly electron rich 2'-hydroxychalcone dienophiles via electron transfer-initiated Diels-Alder cycloaddition is described. Using the methodology, the total synthesis of nicolaiodesin C has been accomplished.