(+)-Fustin | 4382-36-9

• 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: (+)-Fustin
• 英文别名: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-2,3-dihydrochromen-4-one
• CAS: 4382-36-9
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: FNUPUYFWZXZMIE-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-Fustin 在 间苯三酚 作用下， 以 乙酸乙酯 为溶剂， 反应 9.0h， 以28%的产率得到漆黄素 ( 紫铆素)
  参考文献：
  名称：

  α-酮醇的光化学脱氧：二氢黄酮醇-黄酮酮转化

  摘要：

  在无水乙酸乙酯中辐照光学纯的2,3-反-3-羟基黄酮类化合物直接导致游离酚类黄烷酮类似物的完全保留在C（2）的配置。类似地，它们的甲基醚得到相应的黄烷酮和黄酮。该反应代表在Clemmensen条件下还原的光化学当量。

  DOI：

  10.1039/p19800001003
• 作为产物：
  描述：

  3,4-双(甲氧基甲氧基)苯甲醛 在 盐酸 、 氢氧化钾 、 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 34.25h， 生成 (+)-Fustin
  参考文献：
  名称：

  Takahashi, Hiroshi; Kubota, Yumiko; Igushi, Mieko, Heterocycles, 1986, vol. 24, # 2, p. 369 - 377

  摘要：

  DOI：

文献信息

• Kinetic Model for the Antiradical Activity of the Isolated <i>p</i>-Catechol Group in Flavanone Type Structures Using the Free Stable Radical 2,2-Diphenyl-1-picrylhydrazyl as the Antiradical Probe
  作者：José M. Sendra、Enrique Sentandreu、José L. Navarro

  DOI：10.1021/jf070689s

  日期：2007.7.1

  acetonitrile the reduction curves completely lacked the slow kinetics step. From the results, a kinetic model for the reaction of reduction of the DPPH* by the isolated p-catechol group in flavanone type structures is proposed. According to this model, the p-catechol group rapidly transfers two hydrogen atoms to DPPH*, through a fast rate constant k1, yielding the corresponding o-quinone. Then, the intermediate

  三种溶剂中含有分离的对儿茶酚基团的黄烷酮（紫杉醇，二十烷三醇，分光光度法和液相质谱法测定了反应混合物质谱的时间演化。在含酒精的溶剂中，还原曲线由最初的短暂但快速的动力学步骤组成，随后是较长的缓慢的动力学步骤；相反，在乙腈中，还原曲线完全缺少慢动力学步骤。根据结果​​，提出了在黄烷酮类结构中分离的对-邻苯二酚基团还原DPPH *的反应的动力学模型。根据这个模型，对苯二酚基团通过快速速率常数k1将两个氢原子迅速转移至DPPH *，得到相应的邻醌。然后，中间体邻醌通过缓慢的速率常数k 2与醇溶剂形成加合物，并再生对儿茶酚基团。再生的对苯二酚基团通过快速速率常数k3减少了额外的DPPH *，生成了相应的邻苯二酚，邻苯二酚可与溶剂形成新的加合物以再生对苯二酚基团，依此类推。从动力学模型中，导出了两个非常明确的动力学方程式，它们非常适合从所进行的所有实验中从所有被测化合物中获得的实验数据点，从而可以准
• Metabolites from the purple heartwood of mimosoideae. Part 3. Acacia crombei C. T. White: structure and partial synthesis of crombenin, a natural spiropeltogynoid
  作者：Edward V. Brandt、Daneel Ferreira、David G. Roux

  DOI：10.1039/p19810001879

  日期：——

  pirobenzofuran-3(2H)-one, the first spiropeltogynoid, is related to the concomitant crombeone (8-hydroxypeltogynone) from which it is derived via oxidation with alkaline hydrogen peroxide of the chalcone intermediate. The method of synthesis and i.r. spectroscopy define the stereochemistry as either 2(3′)R,4′R or 2(3′)S,4′S. Crombenin is accompanied by the first natural 5,6-dihydroxyphthalide.

  Crombenin，4,4'，6,6'，7- pentahydroxyisochroman -3'- spirobenzofuran-3（2 ħ） -酮，第一spiropeltogynoid，是关系到伴随crombeone（8- hydroxypeltogynone）从其衍生自通过查尔酮中间体用碱性过氧化氢氧化。合成和红外光谱法将立体化学定义为2（3'）R，4'R或2（3'）S，4 'S。crombenin伴随着第一个天然的5,6-二羟基邻苯二酚。
• Synthesis and Cyclization of 1-(2-Hydroxyphenyl)-2-propen-1-one Epoxides:  3-Hydroxychromanones and -flavanones <i>versus</i> 2-(1-Hydroxyalkyl)-3-coumaranones
  作者：Tamás Patonay、Albert Lévai、Csaba Nemes、Tibor Timár、Gábor Tóth、Waldemar Adam

  DOI：10.1021/jo960163z

  日期：1996.1.1

  Competitive alpha and beta cyclization of 2'-hydroxychalcone epoxides affords 2-(alpha-hydroxybenzyl)-3-coumaranone and/or 3-hydroxyflavanones, which depends on the conditions employed. Epoxidation of 2'-hydroxychalcones by dimethyldioxirane followed by either base- or acid-catalyzed ring closure provides a novel, general, and efficient method for the synthesis of trans-3-hydroxyflavanones, which includes also the naturally occurring derivatives. Extension of this two-step procedure to 1-(2-hydroxyphenyl)-2-alken-1-ones was also accomplished. A strong preference for alpha cyclization was observed in the case of beta-unsubstituted or -monoalkylated alpha,beta-enones, while both 2,2-dimethyl-3-hydroxychromanones and 2-(1-hydroxy-1-methylethyl)-3-coumaranones were obtained from the beta,beta-dimethylated substrates.
• FLAVONOIDDERIVAT ZUR BEHANDLUNG VON ZAHNKARIES
  申请人：Mühlbauer Technology GmbH

  公开号：EP4017585A1

  公开（公告）日：2022-06-29
• Rhus Verniciflua Stokes Extract Having Increased Content Of Active Flavonoid Compound And Method For Preparing Same
  申请人：Park Sang-Jae

  公开号：US20120283322A1

  公开（公告）日：2012-11-08

  The present invention relates to Rhus verniciflua Stokes extract having an increased content of an active flavonoid compound through a gas bubbling treatment, a method for preparing the Rhus verniciflua Stokes extract, and a method for converting fustin into fisetin through the gas bubbling treatment of a solution containing fustin. The method for preparing the Rhus verniciflua Stokes extract of the present invention can convert the conventional Rhus verniciflua Stokes extract having high content of fustin and low content of fisetin into a Rhus verniciflua Stokes extract having high content of fisetin. Therefore, the Rhus verniciflua Stokes extract of the present invention can be commercialized into natural anticancer agents, anticancer and cancer prevention food products, and health functional foods due to the excellent bioactivity thereof, and promote the development of relevant industries through the high added-value of Rhus verniciflua Stokes. In addition, the method for converting fustin into fisetin can be applied to other natural substances and be used as a method for enhancing the functionality thereof by increasing the content of a high active flavonoid, thereby becoming an enabling technology that can lead high-functionalization of natural substances.