Hesperetin-triacetat | 6274-73-3

• 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: Hesperetin-triacetat
• 英文别名: Hesperetic triacetate；[5-acetyloxy-2-(3-acetyloxy-4-methoxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl] acetate
• CAS: 6274-73-3
• 化学式: C₂₂H₂₀O₉
• 分子量: 428.395
• InChiKey: JXQZPLOAXXMSJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Hesperetin-triacetat 在 sodium hydroxide 、 乙醇 、 氯仿 、 溴 作用下， 生成 香叶木素
  参考文献：
  名称：

  Zemplen; Bognar, Chemische Berichte, 1943, vol. 76, p. 452,457

  摘要：

  DOI：
• 作为产物：
  描述：

  橙皮甙 在 吡啶 、 硫酸 作用下， 生成 Hesperetin-triacetat
  参考文献：
  名称：

  Arthur et al., Journal of the Chemical Society, 1956, p. 632,634

  摘要：

  DOI：

文献信息

• Reduction de flavanones par le cyanoborohydrure de sodium dans l'acide trifluoroacetique - I/
  作者：Guy Lewin、Maryse Bert、Jean-Claude Dauguet、Corinne Schaeffer、Jean-Luc Guinamant、Jean-Paul Volland

  DOI：10.1016/s0040-4039(01)93420-3

  日期：——

  Reduction of natural flavanones with NaBH3CN in CF3COOH gives, depending on substituents 7 and 4′, either flavanes or 1,3-diaryl propanes.

  在CF 3 COOH中用NaBH 3 CN还原天然黄烷酮，取决于取代基7和4'，产生黄烷或1,3-二芳基丙烷。
• Lipase-catalysed selective deacetylation of peracetylated benzopyranones
  作者：Virinder S. Parmar、Ashok K. Prasad、Nawal K. Sharma、Anand Vardhan、Hari N. Pati、Sunil K. Sharma、Kirpal S. Bisht

  DOI：10.1039/c39930000027

  日期：——

  Molecular recognition has been observed in the hydrolysis of peracetates of benzopyranones by lipases from porcine pancreas and Candida cylindracea in organic solvents; the acetoxy group(s) at positions other than peri or ortho to the carbonyl group are hydrolysed preferentially.

  在有机溶剂中，猪胰腺脂肪酶和圆筒状念珠菌对苯并吡喃酮过乙酸酯的水解反应中观察到了分子识别现象；羰基以外或羰基正位上的乙酰氧基优先水解。
• 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.
• Asahina; Shinoda; Inubuse, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1928, vol. 48, p. 29
  作者：Asahina、Shinoda、Inubuse

  DOI：——

  日期：——
• Dihydrochalcone sweeteners. A study of the atypical temporal phenomena
  作者：Grant E. DuBois、Guy A. Crosby、Rebecca A. Stephenson

  DOI：10.1021/jm00136a011

  日期：1981.4

  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.