6-glucosyloxy-7-hydroxycoumarin | 139560-95-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-glucosyloxy-7-hydroxycoumarin
• 英文别名: esculin；esculoside；6,7-Dihydroxy-cumarin-6-glucosid；Esculetin-6-glucoside；7-hydroxy-6-[[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-1-benzopyran-2-one；7-hydroxy-6-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
• CAS: 139560-95-5
• 化学式: C₁₅H₁₆O₉
• 分子量: 340.287
• InChiKey: XHCADAYNFIFUHF-GSZWNOCJSA-N

物化性质

• 沸点：
  697.7±55.0 °C(Predicted)
• 密度：
  1.679±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-glucosyloxy-7-hydroxycoumarin 在 硫酸 作用下， 生成 D-葡萄糖 、 6,7-二羟基香豆素
  参考文献：
  名称：

  Coumarins from bark of Fraxinus japonica and F. mandshurica var. japonica.

  摘要：

  从水曲柳树皮中新分离出了两种具有生物活性的香豆素：东莨菪素 (1) 和异曲西丁 (2)，以及已知的香豆素：七叶亭 (3)、七叶亭 (4)、七叶亭 (5) 和 fraxin (6)。 （木犀科）。另一方面，F. mandshurica RUPR 的树皮。变种japonica MAXIM 仅提供已知的香豆素、fraxetin (4)、fraxinol (7) 和 mandshurin (8)。

  DOI：

  10.1248/cpb.33.4069

文献信息

• Water Soluble and Activable Phenolics Derivatives with Dermocosmetic and Therapeutic Applications and Process for Preparing Said Derivatives
  申请人：Auriol Daniel

  公开号：US20090233876A1

  公开（公告）日：2009-09-17

  The invention relates to the preparation of phenolics derivatives by enzymatic condensation of phenolics selected among pyrocatechol or its derivatives with the glucose moiety of sucrose. The production of said phenolics derivatives is achieved with a glucosyltransferase (EC 2.4.1.5). These O-α-glucosides of selected phenolics are new, have a solubility in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compositions, such as antioxidative, antiviral, antibacterial, immune-stimulating, antiallergic, antihypertensive, antiischemic, antiarrhythmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application.

  该发明涉及通过酶催化将选择自间苯二酚或其衍生物的酚类与蔗糖的葡萄糖部分进行缩合来制备酚类衍生物。所述酚类衍生物的生产是通过葡萄糖转移酶（EC 2.4.1.5）实现的。所选酚类的这些O-α-葡糖苷是新的，其在水中的溶解度高于它们的原始多酚，并且在化妆品和药用组合物中具有有用的应用，如抗氧化、抗病毒、抗菌、免疫刺激、抗过敏、降压、抗缺血、抗心律失常、抗血栓形成、降胆固醇、抗脂质过氧化、肝脏保护、抗炎症、抗癌变突变、抗肿瘤、抗血栓形成和扩血管等配方，或者在任何其他应用领域中。
• Esculetin derivatives, method for manufacture thereof, and pharmaceutical composition
  申请人：Kureha Chemical Industry Co., Ltd.

  公开号：EP0719770A1

  公开（公告）日：1996-07-03

  A compound of the formula (I): wherein R1 and R2 are, independently, -CON(R4)R5, or a monosaccharide, or acylated monosaccharide group, with the proviso that at least one of R1 and R2 is -CON(R4)R5, and R4 and R5 are, independently, a hydrogen atom, or a hydroxyl, alkyl, aryl, or aralkyl group, or R4 and R5 together with the nitrogen atom attached thereto form a 3- to 7-membered saturated cycloaliphatic amino group, and R3 is a hydrogen atom, or a hydroxyl, alkyl, aryl, aralkyl, or -COOR8 group, and R3 is at 3- or 4-position, and R8 is a hydrogen atom or an alkyl group, or a salt thereof is disclosed. The compound has a function to inhibit a matrix metalloproteinase.

  式 (I) 的化合物： 其中 R1 和 R2 独立地为-CON(R4)R5，或单糖，或酰化单糖基团，但 R1 和 R2 中至少有一个为-CON(R4)R5，且 R4 和 R5 独立地为氢原子，或羟基、烷基、芳基或芳烷基、或 R4 和 R5 与相连的氮原子一起形成 3 至 7 元饱和环脂族氨基，且 R3 是氢原子，或羟基、烷基、芳基、芳烷基或 -COOR8 基团，且 R3 位于 3 位或 4 位，且 R8 是氢原子或烷基，或公开了其盐。该化合物具有抑制基质金属蛋白酶的功能。
• Water soluble phenolics derivatives with dermocosmetic and therapeutic applications
  申请人：Libragen

  公开号：EP1867729A1

  公开（公告）日：2007-12-19

  The invention relates to the preparation of phenolics derivatives by enzymatic condensation of phenolics selected among pyrocatechol or its derivatives including (i) protocatechuic acid and its derivatives, (ii) 3,4-dihydroxycinnamic acid with its transisomer or caffeic acid and its derivatives, especially hydrocaffeic acid, rosmarinic acid, chlorogenic acid and caffeic acid phenethyl ester, and with its cis-isomer and its derivatives, especially esculin, (iii) dihydroxyphenylglycol, and (iv) members of the flavonoid familly such as taxifolin and fustin (dihydroflavonols), fisetin (a flavonol), eriodictyol (a flavanone), , with the glucose moiety of sucrose. The production of said phenolics derivatives is achieved with a glucosyltransferase (EC 2.4.1.5) obtained from a culture of Leuconostoc species, and more particularly from the culture of Leuconostoc mesenteroides NRRL B-512F. These O-glucosides of selected phenolics are new, have a solubility in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compositions, such as antioxidative, antiviral, antibacterial, immune-stimulating, antiallergic, antihypertensive, antiischemic, antiarrhytmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application. All the more, glucosylated phenolics derivatives objects of the invention can be hydrolyzed by the human natural microbiotes, thus releasing the active part of the phenolic compound upon time during their usage or by an α-glucosidase (EC 3.2.1.20).

  本发明涉及用酶缩合法制备酚类衍生物，所选酚类包括焦儿茶酚或其衍生物，包括(i) 原儿茶酸及其衍生物，(ii) 3,4-二羟基肉桂酸与其反式异构体或咖啡酸及其衍生物，特别是氢咖啡酸、(iii) 二羟基苯甘醇，以及 (iv) 黄酮家族成员，如 taxifolin 和 fustin（二氢黄酮醇）、fisetin（一种黄酮醇）、eriodictyol（一种黄酮），以及蔗糖的葡萄糖分子。上述酚类衍生物的生产是通过一种葡糖基转移酶（EC 2.4.1.5）实现的，该酶是从白色念珠菌（Leuconostoc species）的培养物中获得的，尤其是从中肠白色念珠菌（Leuconostoc mesenteroides NRRL B-512F）的培养物中获得的。抗高血压、抗缺血、抗心律失常、抗血栓、降胆固醇、抗脂过氧化、保肝、抗炎、抗癌、抗突变、抗肿瘤、抗血栓和血管扩张配方，或任何其他应用领域。此外，本发明的葡糖基化酚类衍生物可被人体天然微生物水解，从而在使用过程中或通过α-葡萄糖苷酶（EC 3.2.1.20）释放出酚类化合物的活性部分。
• Esculetin derivatives and method for manufacture thereof, use thereof, and pharmaceutical composition
  申请人：KUREHA CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0654479B1

  公开（公告）日：2000-03-15
• Phenolic compounds with cosmetic and therapeutic applications
  申请人：Libragen

  公开号：EP2027279B1

  公开（公告）日：2012-04-18