dihydroquercetin 3,3',4',7-tetraacetate

• 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: dihydroquercetin 3,3',4',7-tetraacetate
• 英文别名: [(2R,3R)-7-acetyloxy-2-(3,4-diacetyloxyphenyl)-5-hydroxy-4-oxo-2,3-dihydrochromen-3-yl] acetate
• 化学式: C₂₃H₂₀O₁₁
• 分子量: 472.405
• InChiKey: JYNJWKIFSPJVHZ-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  dihydroquercetin 3,3',4',7-tetraacetate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以53%的产率得到6,8-dibromodihydroquercetin 3,7,3',4'-tetraacetate
  参考文献：
  名称：

  二氢槲皮素醋酸酯的差向异构化、转酰化和溴化；8-溴二氢槲皮素的合成

  摘要：

  二氢槲皮素 (dhq) 及其 3-乙酸酯在没有碱催化剂的情况下与乙酸酐反应，生成部分乙酰化产物的混合物。三种新酯通过 NMR 光谱表征为 dhq 3,7,3'-三乙酸酯、3,7,4'-三乙酸酯和 5,7,3',4'-四乙酸酯。在其熔点，纯 dhq 3,7,3',4'-四乙酸酯通过分子间乙酰转移部分转化为 dhq 3,3',4'-三乙酸酯和 dhq 五乙酸酯。在这些条件下，Dhq 7,3',4'-三乙酸酯仅产生 dhq 3',4'-二-和 3,7,3',4'-四乙酸酯。乙酰化/去乙酰化反应伴随着部分差向异构化：鉴定出 3 种具有 2,3-顺式立体化学（dhq 3-, 3,7,3',4'-tetra- 和 penta-）的新乙酸酯。Dhq 及其 3,7,3',

  DOI：

  10.2478/s11532-011-0032-8
• 作为产物：
  描述：

  taxifolin pentaacetate 在 硫酸 作用下， 生成 dihydroquercetin 3,3',4',7-tetraacetate
  参考文献：
  名称：

  Brewerton; Cambie, 1959, vol. 2, p. 95,96

  摘要：

  DOI：

文献信息

• Crystal structures of dihydroquercetin 3-acetate and dihydroquercetin 3,3<i>'</i>4<i>'</i>,7-tetraacetate: hydrogen bonding in 5-hydroxyflavanones
  作者：Eberhard Kiehlmann、Kumar Biradha、Konstantin V Domasevitch、Michael J Zaworotko

  DOI：10.1139/v99-140

  日期：1999.8.1

  The molecular structures of dihydroquercetin 3-acetate 3 and dihydroquercetin 3,3',4',7-tetraacetate 4 were determined by single crystal X-ray analysis. Comparison of their crystal data with those of 16 known 5-hydroxyflavanones shows intramolecular O(5)-H···O(4)=C hydrogen bonding, preference for nearly perpendicular orientation of the two aromatic rings and preferred sofa conformation of the heterocyclic ring. The major stabilizing force in the crystal packing pattern of 3 is intermolecular hydrogen bonding.Key words: crystal structure, dihydroquercetin, flavanones, hydrogen bonding.

  二氢槲皮素3-醋酸酯和二氢槲皮素3,3',4',7-四醋酸酯的分子结构是通过单晶X射线分析确定的。将它们的晶体数据与16种已知的5-羟基黄酮类化合物进行比较，显示了分子内O(5)-H···O(4)=C氢键的存在，以及两个芳香环几乎垂直取向和杂环环的偏好沙发构象。化合物3的晶体包装模式中的主要稳定力是分子间氢键。关键词：晶体结构、二氢槲皮素、黄酮类化合物、氢键。
• Inhibitory Compound of Tyrosinase Activity from the Sprout of Polygonum hydropiper L. (Benitade)
  作者：Mitsuo Miyazawa、Naotaka Tamura

  DOI：10.1248/bpb.30.595

  日期：——

  A tyrosinase inhibitor was isolated from the sprout of Polygonum hydropiper L. (Benitade) by activity-guided fractionation and identified as (2R,3R)-(+)-taxifolin (1) by spectroscopic means. Compound 1 inhibited 70% of tyrosinase activity at a concentration of 0.50 mM. ID50 (50% inhibition dose) value of compound 1 was 0.24 mM. As compared with tyrosinase inhibitor known cosmetic agent such as arbutin and kojic acid, compound 1 was more inhibited than the former and showed inhibitory effect equal to that of the latter. To study the inhibitory effect of (2R,3R)-(+)-taxifolin derivatives against tyrosinase activity, 3,7,3′,4′-taxifolin tetraacetate (2) and 5,7,3′,4′-taxifolin teramethyl ether (3) were also assayed together with compound 1.

  从Polygonum hydropiper L.（香葱）的芽中通过活性引导分馏分离出了一种酪氨酸酶抑制剂，并通过光谱法鉴定为(2R,3R)-(+)-taxifolin (1)。化合物1在0.50 mM的浓度下抑制了70%的酪氨酸酶活性。化合物1的ID50（50%抑制剂量）值为0.24 mM。与已知的酪氨酸酶抑制剂化妆品成分，如熊果苷和曲酸相比，化合物1对前者的抑制效果更强，对后者的抑制效果相当。为了研究(2R,3R)-(+)-taxifolin衍生物对酪氨酸酶活性的抑制作用，3,7,3′,4′-taxifolin四乙酰酸酯（2）和5,7,3′,4′-taxifolin三甲醚（3）也与化合物1一起进行了测试。
• Five diterpenes and other constituents from nine Baccharis species
  作者：Ferdinand Bohlmann、Christa Zdero、Michael Grenz、Autar K. Dhar、Harold Robinson、Robert M. King

  DOI：10.1016/0031-9422(81)85107-2

  日期：1981.1

  Abstract The investigation of nine Baccharis species afforded, in addition to known compounds, three new clerodane derivatives related to bacchotricuneatin B, two ent -labdane derivatives, two 3-acetoxyflavanones, a benzofuran derivative and a chromene. The overall picture of the chemistry of this large genus is still not very clear.

  摘要 除已知化合物外，对九种 Baccharis 的研究还提供了三种与 bacchotricuneatin B 相关的新克罗丹衍生物、两种 ent-labdane 衍生物、两种 3-乙酰氧基黄烷酮、一种苯并呋喃衍生物和一种色烯。这个大属的化学整体图仍然不是很清楚。
• PREPARATION AND PARTIAL DEACETYLATION OF DIHYDROQUERCETIN ACETATES
  作者：E. Kiehlmann

  DOI：10.1080/00304949909355676

  日期：1999.2
• Methylation of Dihydroquercetin Acetates:  Synthesis of 5-<i>O</i>-Methyldihydroquercetin
  作者：Eberhard Kiehlmann、Peter W. Slade

  DOI：10.1021/np034005w

  日期：2003.12.1

  The major products of methylation of dihydroquercetin (1, dhq) with diazomethane have been identified as 7-O-methyldhq (9), 7,3'-di-0-methyldhq (10), 7,4'-di-O-methyldhq (11), and 7,3',4'-tri-O-methyldhq (2). With dhq 3,7,3',4'-tetraacetate (6), dhq 3,5,3',4'-tetraacetate (5), dhq 3,3',4'-triacetate (7), dhq 7,3',4'triacetate (8), and dhq 3-acetate (4) the same reaction affords mainly 5-O-methyldhq 3,7,3',4'-tetraacetate (15), 7-O-methyldhq 3,5,3',4'-tetraacetate (13), 7-O-methyldhq 3,3',4'-triacetate (14), 5-O-methyldhq 7,3',4'triacetate (25), and 7-O-methyldhq 3-acetate (12), respectively. The methylation of 8 is accompanied by intermolecular acetyl migration from phenolic oxygen to the hydroxy group of the heterocyclic ring. 5-O-Methyldhq (28) is accessible by deacetylation of 25. 5,7-Di-O-methyldhq (29), four known methyl ethers, 13 new and three known methyl ether acetates of dhq, and six new isomers with 2,3-cis stereochemistry were spectroscopically identified.