3',5,7-triacetoxy-4'-methoxyflavone | 3162-05-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3',5,7-triacetoxy-4'-methoxyflavone
• 英文别名: 5,7-diacetoxy-2-(3-acetoxy-4-methoxy-phenyl)-chromen-4-one；5,7-Diacetoxy-2-(3-acetoxy-4-methoxy-phenyl)-chromen-4-on；5,7-bis(acetyloxy)-2-[3-(acetyloxy)-4-methoxyphenyl]-4H-1-benzopyran-4-one；Tri-O-acetyl-oriopmetin；Diosmetin-triacetat；Diosmetintriacetat；[5-acetyloxy-2-(3-acetyloxy-4-methoxyphenyl)-4-oxochromen-7-yl] acetate
• CAS: 3162-05-8
• 化学式: C₂₂H₁₈O₉
• 分子量: 426.38
• InChiKey: KYVRTXVVKJGTBD-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C
• 沸点：
  581.1±50.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  3',5,7-triacetoxy-4'-methoxyflavone 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 以96%的产率得到香叶木素
  参考文献：
  名称：

  Dihydrochalcone sweeteners. A study of the atypical temporal phenomena

  摘要：

  Neohesperidin dihydrochalcone (NHDHC), known since 1963 as an intensely sweet compound, is determined to be 340 +/- 60 (p less than 0.05) times more potent than sucrose. The unusual temporal properties of this material are hypothesized as being due to the effects of metabolism, conformation, chelation, or hydrophobicity. Forty-four analogues are synthesized to test the four hypotheses, none of which are strongly supported. A method of quantitation of temporal characteristics of tastant molecules is developed so as to allow comparison of taste appearance time (AT) and extinction time (ET) of experimental compounds. Four of the new compounds, 40 and 43-45, exhibit high sweetness potencies, ranging from 280 and 440 times sucrose, and may be useful in selected food systems. The temporal taste characteristics remain unimproved over NHDHC, however.

  DOI：

  10.1021/jm00136a011
• 作为产物：
  描述：

  (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 23.0h， 生成 3',5,7-triacetoxy-4'-methoxyflavone
  参考文献：
  名称：

  Dihydrochalcone sweeteners. A study of the atypical temporal phenomena

  摘要：

  Neohesperidin dihydrochalcone (NHDHC), known since 1963 as an intensely sweet compound, is determined to be 340 +/- 60 (p less than 0.05) times more potent than sucrose. The unusual temporal properties of this material are hypothesized as being due to the effects of metabolism, conformation, chelation, or hydrophobicity. Forty-four analogues are synthesized to test the four hypotheses, none of which are strongly supported. A method of quantitation of temporal characteristics of tastant molecules is developed so as to allow comparison of taste appearance time (AT) and extinction time (ET) of experimental compounds. Four of the new compounds, 40 and 43-45, exhibit high sweetness potencies, ranging from 280 and 440 times sucrose, and may be useful in selected food systems. The temporal taste characteristics remain unimproved over NHDHC, however.

  DOI：

  10.1021/jm00136a011

文献信息

• Synthesis, characterization, anti-inflammatory and anti-proliferative activity against MCF-7 cells of O-alkyl and O-acyl flavonoid derivatives
  作者：T. Kim-Dung Hoang、T. Kim-Chi Huynh、Thanh-Danh Nguyen

  DOI：10.1016/j.bioorg.2015.09.005

  日期：2015.12

  A series of O-alkyl and O-acyl flavonoid derivatives was synthesized in high efficiency. Alkylation and acylation of 5-hydroxyflavonoids showed that the low reactivity hydroxyl group, 5-OH, well reacted with strong reagents whereas with weaker reagents, the different products were obtained dependently on structural characteristic of ring C of respective flavonoid. In order to evaluate anti-inflammatory activity, all compounds were tested for in vitro inhibition of bovine serum albumin denaturation and in vivo inhibition of carrageenan-induced mouse paw edema. Among them, the compounds 3, 3b, 4b and 4c demonstrated more effective anti-inflammatory activity than standard drugs (diclofenac sodium and ketoprofen) in both tests. Meanwhile, the flavonoids 2, 2c, 3a and 4b displayed anti-proliferative activity against MCF-7 cell lines. Triacetyl derivative of hesperetin 4b inducing degradation of DNA in MCF-7 cells was observed. (C) 2015 Elsevier Inc. All rights reserved.
• Zemplen; Bognar, Chemische Berichte, 1943, vol. 76, p. 452,457
  作者：Zemplen、Bognar

  DOI：——

  日期：——
• Notes- A New Procedure for the Dehydragenation of Flavanones with N-Bromosuccinimide
  作者：J Looker、Myron Holm

  DOI：10.1021/jo01086a609

  日期：1959.4
• CVIII.—Anthoxanthins. Part XI. A synthesis of diosmetin and of luteolin 3′-methyl ether
  作者：Albert Lovecy、Robert Robinson、Shigehiko Sugasawa

  DOI：10.1039/jr9300000817

  日期：——
• Teoule et al., Bulletin de la Societe Chimique de France, 1959, p. 854
  作者：Teoule et al.

  DOI：——

  日期：——