4-羟基-3-(4-羟基苯基)-5-甲氧基-8,8-二甲基-6-(3-甲基-2-丁烯-1-基)-2H,8H-吡喃并[2,3-f]苯并吡喃-2-酮 | 5084-00-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 4-羟基-3-(4-羟基苯基)-5-甲氧基-8,8-二甲基-6-(3-甲基-2-丁烯-1-基)-2H,8H-吡喃并[2,3-f]苯并吡喃-2-酮
• 英文名称: scandenin
• 英文别名: 4-hydroxy-3-(4-hydroxyphenyl)-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-2-one
• CAS: 5084-00-4
• 化学式: C₂₆H₂₆O₆
• 分子量: 434.489
• InChiKey: AAKJUGSASOCUFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-羟基-3-(4-羟基苯基)-5-甲氧基-8,8-二甲基-6-(3-甲基-2-丁烯-1-基)-2H,8H-吡喃并[2,3-f]苯并吡喃-2-酮 在 溴 、 溶剂黄146 作用下， 生成 6-(2,3-dibromo-3-methyl-butyl)-4-hydroxy-3-(4-hydroxy-phenyl)-5-methoxy-8,8-dimethyl-8H-pyrano[2,3-f]chromen-2-one
  参考文献：
  名称：

  Murti et al., Proceedings - Indian Academy of Sciences, Section A, 1948, # 27, p. 111,118, 119

  摘要：

  DOI：

文献信息

• 13C NMR studies of some complex natural oxygen heterocyclics
  作者：K.V.Subba Raju、G. Srimannarayana、B. Ternai、R. Stanley、K.R. Markham

  DOI：10.1016/s0040-4020(01)97667-7

  日期：1981.1

  13C NMR spectra for a variety of isoflavones are presented and analysed. The novel isoflavone, Millettin (Xa) is shown to be closely related to Auriculatin (II). While comparison of the 13C NMR spectra did not readily prove the orientation of the fused pyran ring, the use of acetylation shifts showed unambiguously that the fusion in linear, rather than angular.

  给出并分析了各种异黄酮的13 C NMR光谱。小说中的异黄酮Millettin（Xa）与Auriculatin（II）密切相关。尽管13 C NMR谱图的比较不能轻易证明稠合吡喃环的方向，但是乙酰化位移的使用清楚地表明融合是线性的，而不是角度的。
• Isolation, Semi-Synthesis and Antifeedant Activity of Constituents from Derris scandens Benth.
  作者：P. Poorna、K. Ramakrishna、M. Suri Appa Rao

  DOI：10.14233/ajchem.2020.22801

  日期：——

  This work describes the semi-synthesis of derivatives from derris isoflavone-A (1), scandenin (2) and 6,8-diprenyl-4′,5,7-trihydroxy isoflavone (3) which are major constituents isolated from chloroform extract of Derris scandens Benth. All the semi-synthesized derivatives (4-11) were characterized by NMR and mass spectroscopic techniques. All these derivatives are evaluated for their antifeedant activity

  这项工作描述了鱼藤异黄酮-A (1)、鱼藤素 (2) 和 6,8-二异戊二烯基-4',5,7-三羟基异黄酮 (3) 衍生物的半合成，这些衍生物是从鱼藤氯仿提取物中分离出来的主要成分。德里斯扫描了本斯。所有半合成衍生物(4-11)均通过核磁共振和质谱技术进行表征。使用非选择实验室生物测定法评估所有这些衍生物对蓖麻半翅虫和烟草毛虫的拒食活性。结果表明，scandenin (2)、化合物 5、7 和 10 具有有效的杀虫活性。
• Isoflavonoids from Derris spruceana
  作者：Marcos Garcia、Marli Hiroco C. Kano、Durval Marcos Vieira、Maria Célia Do Nascimento、Walter B. Mors

  DOI：10.1016/s0031-9422(00)81713-6

  日期：1986.1
• COMPOUNDS, COMPOSITIONS AND METHODS FOR PREVENTING SKIN DARKENING
  申请人：Orlow Seth J.

  公开号：US20110190229A1

  公开（公告）日：2011-08-04

  A method for preventing hyperpigmented skin, undesired pigmentation disorder of skin, or undesired darkening of skin using coumarin compounds, the use of such compounds, and compositions and formulations thereof are disclosed. In a particular embodiment, the coumarin compounds are selected from robustic acid methyl ether, scandenin, and coumophos. The compounds may be prepared as additives to pharmaceutical and cosmetic compositions, and in personal care products such as antiperspirants. In a particular embodiment extends to an antiperspirant product containing a skin darkening inhibitory amount of a compound of the invention. Also, the present skin darkening compounds may be prepared in combination with each other. The compounds, compositions and formulations of the invention may be used for the prevention of the onset or progression of conditions characterized by unwanted skin darkening, including those that may be causally related to aberrant melanogenesis activity including, by way of non-limiting example, hyperpigmentation and others.
• COUMARIN COMPOUNDS AS MELANOGENESIS MODIFIERS AND USES THEREOF
  申请人：ORLOW Seth J.

  公开号：US20120220545A1

  公开（公告）日：2012-08-30

  Provided are coumarin compounds of formula I, for example, robustic acid methyl ether, and the use of such compounds and compositions thereof to modulate (e.g., inhibit) melanogenesis and pigmentation. wherein R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are described herein. Also provided are plant extracts containing a compound of formula I, and the use of such a plant extract to modulate (e.g., inhibit) melanogenesis and pigmentation. The compound or plant extract may be prepared as pharmaceutical and cosmetic compositions, and may be used for the prevention and treatment of conditions that are related to aberrant melanogenesis activity.