Hydrangeaic acid | 491-79-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: Hydrangeaic acid
• 英文别名: (E)-2-hydroxy-6-(4-hydroxystyryl)benzoic acid；hydrangenic acid；hydrangeic acid；3,4'-dihydroxy-trans-stilbene-2-carboxylic acid；3,4'-dihydroxy-stilbene-2-carboxylic acid；3,4'-Dihydroxy-trans-stilben-2-carbonsaeure；2-hydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]benzoic acid
• CAS: 491-79-2；113428-99-2
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: UWXXIBUTKVUHTR-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Hydrangeaic acid 在 sodium amalgam 、 sodium carbonate 作用下， 生成 半月苔酸
  参考文献：
  名称：

  Asahina; Asano, Chemische Berichte, 1930, vol. 63, p. 429,435

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-6-甲基苯甲酸 在 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 sodium tungstate (VI) dihydrate 、 偶氮二异丁腈 、 双氧水 、 sodium hydride 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 49.08h， 生成 Hydrangeaic acid
  参考文献：
  名称：

  合成月桂酸，羟橙酸及其类似物的重要组成部分。

  摘要：

  合成了一种新的基于功能化砜的结构单元，该结构单元可通过朱莉娅烯化反应形成CC键。通过成功合成两种天然产物月桂酸，羟橙酸及其类似物的初始文库，证明了已开发构件的实用性。

  DOI：

  10.1080/14786419.2016.1274891

文献信息

• Development of Bioactive Functions in Hydrangeae Dulcis Folium. VI. Syntheses of Thunberginols A and F and Their 3'-Deoxy-Derivatives Using Regiospecific Lactonization of Stilbene Carboxylic Acid: Structures and Inhibitory Activity on Histamine Release of Hydramacrophyllols A and B.
  作者：Masayuki YOSHIKAWA、Hiromi SHIMADA、Nobuhiro YAGI、Nobutoshi MURAKAMI、Hiroshi SHIMODA、Johji YAMAHARA、Hisashi MATSUDA

  DOI：10.1248/cpb.44.1890

  日期：——

  Lactonization reaction of 2-carboxystilbene mediated by copper(II) chloride proceeded regiospecifically to give the five-membered lactone, while the bromolactonizations using N-bromosuccinimide and anodic oxidation were found to furnish the six-membered lactone. Using these regiospecific lactonization reactions as a key step, antiallergic and antimicrobial isocoumarins and the benzylidenephthalides thunberginols A and F and their 3'-deoxyanalogs were synthesized from phyllodulcin and hydrangenol.Two phthalides called hydramacrophyllols A and B were isolated from Hydrangeae Dulcis Folium and their stereostructures were determined on the basis of physicochemical and chemical evidence, which included the syntheses of hydramacrophyllols A and B from hydrangenol by the application of the lactonization method using copper(II)chloride. In addition, hydramacrophyllols A and B were found to exhibit an inhibitory effect on the histamine release from rat peritoneal exudate cells induced by antigen-antibody reaction.

  氯化铜（II）介导的 2-羧基二苯乙烯的内酯化反应进行了区域特异性反应，生成了五元内酯，而使用 N-溴代琥珀酰亚胺和阳极氧化进行的溴内酯化反应则生成了六元内酯。利用这些区域特异性内酯化反应作为关键步骤，从phyllodulcin 和 hydrangenol 合成了抗过敏和抗菌的异香豆素和苯亚甲基酞thunberginols A 和 F 及其 3'-deoxyanalogs 。根据物理化学和化学证据，从绣线菊叶中分离出了两种名为水飞蓟醇 A 和 B 的邻苯二甲酸盐，并确定了它们的立体结构，其中包括应用氯化铜（II）内酯化法从水飞蓟醇合成了水飞蓟醇 A 和 B。此外，还发现水合麦考酚 A 和 B 对抗原-抗体反应诱导的大鼠腹腔渗出细胞释放组胺具有抑制作用。
• Chemical Transformation from Dihydroisocoumarin into Benzylidenephthalide by Use of Regiospecific Oxidative Lactonization Mediated by Copper Chloride(II). Syntheses of Thunberginol F and Hydramacrophyllol A and B.
  作者：Masayuki YOSHIKAWA、Emiko HARADA、Nobuhiro YAGI、Yasuhiro OKUNO、Osamu MURAOKA、Hiroshi AOYAMA、Nobutoshi MURAKAMI

  DOI：10.1248/cpb.42.721

  日期：——

  Oxidative lactonization of 2-carboxystilbene mediated by CuCl2 proceeded regiospecifically to give the five-membered lactone. By utilizing this lactonization as a key reaction, chemical transformation from dihydroisocoumarine into benzylidenephthalide was accomplished, and it was applied to structural elucidation of two new phthalide, hydramacrophyllols A and B.

  CuCl2 介导的 2-羧基二苯乙烯的氧化内酯化反应进行区域特异性，得到五元内酯。利用该内酯化反应作为关键反应，完成了从二氢异香豆素到亚苄基苯酞的化学转化，并将其应用于两种新的苯酞——Hydrmacrophyllols A和B的结构解析。
• Compositions containing hypotriglyceridemically active stilbenoids
  申请人：Shaman Pharmaceuticals, Inc.

  公开号：US20020055541A1

  公开（公告）日：2002-05-09

  The use of isolated or purified stilbenoid compounds including longistyline A-2-carboxylic acid as a dietary supplement to mammals suffering from elevated triglyceride levels is described. The invention also relates to the use of such stibenoid compounds in combination with other hypotriglyceridemic agents.

  本发明描述了将孤立或纯化的类脂素化合物，包括长链亮胺酸A-2-羧酸，作为膳食补充剂用于患有升高的甘油三酯水平的哺乳动物。本发明还涉及使用这种类脂素化合物与其他降甘油三酯药物联合使用的方法。
• The Jominy End Quench for Light-Weight Alloy Development
  作者：J.W. Newkirk、D.S. MacKenzie

  DOI：10.1361/105994900770345809

  日期：2000.8.1

  The Jominy end quench test is well known as a method of measuring hardenability in steels. In nonferrous alloys, there is a desire to determine the effect of quenching on final properties after heat treating. The Jominy end quench test offers a method for studying many quenching conditions with a minimum of samples. The potential for developing a new understanding of the complex response of nonferrous alloys to processing conditions, especially quenching, will be presented. Examples of the properties measured on Jominy end quench specimens of aluminum and titanium alloys will be presented.

  众所周知，乔明尼端淬试验是测量钢淬透性的一种方法。在有色金属合金中，人们希望确定淬火对热处理后最终特性的影响。乔明尼端淬试验提供了一种用最少的样品研究多种淬火条件的方法。我们将介绍这种方法的潜力，以便重新认识有色金属合金对加工条件（尤其是淬火）的复杂反应。将举例说明在铝合金和钛合金的乔明尼端淬试样上测量到的特性。
• DRUGS, FOODS AND ORAL COMPOSITIONS CONTAINING STILBENE-TYPE COMPOUNDS
  申请人：Sunstar Inc.

  公开号：EP1161944A1

  公开（公告）日：2001-12-12

  The present invention provides a composition for preventing or treating diseases accompanied by a decrease in bone weight, hypertension and diseases resulting from hypertension, the composition containing, as an active component, at least one member selected from a compound represented by formula (1)    [wherein A and B are the same or different and each represents a halogen atom, an amino group, an amidino group, an anilinoamide group, a mercapto group, a sulfonic acid group, a phosphate group, a carboxy group, a hydroxy C1 to C5 alkyl group, a sugar residue, -OR1 (R1 represents a hydrogen atom, a C1 to C5 alkyl group, a hydroxy C1 to C5 alkyl group or a C2 to C5 alkenyl group.) or -OCOR2 (R2 represents a C1 to C5 alkyl group, a hydroxy C1 to C5 alkyl group or a C2 to C5 alkenyl group.). n and m are the same or different and each is an integer from 0 to 5. There are n A's and m B's each of which may be the same or different.] and its multimers.

  本发明提供了一种用于预防或治疗伴有骨重减轻的疾病、高血压和高血压引起的疾病的组合物，该组合物作为活性成分至少含有一种选自式(1)所代表的化合物的成员 [其中 A 和 B 相同或不同，且各自代表卤素原子、氨基、脒基、苯胺基、巯基、磺酸基、磷酸基、羧基、羟基 C1 至 C5 烷基、糖残基、-OR1（R1 代表氢原子、C1 至 C5 烷基、羟基 C1 至 C5 烷基或 C2 至 C5 烯基。)或 -OCOR2 (R2 代表 C1 至 C5 烷基、羟基 C1 至 C5 烷基或 C2 至 C5 烯基。)。 n 和 m 可相同或不同，且均为 0 至 5 的整数。有 n 个 A 和 m 个 B，每个 A 和 B 可以相同或不同。