robustic acid methyl ester | 5307-60-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: robustic acid methyl ester
• 英文别名: robustic acid methyl ether；robustic acid methylether；SJ000286809；4,5-dimethoxy-3-(4-methoxy-phenyl)-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one；4,5-Dimethoxy-3-(4-methoxy-phenyl)-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-on；Robustinsaeure-methylester；5,6-dimethoxy-7-(4-methoxyphenyl)-2,2-dimethylpyrano[3,2-g]chromen-8-one
• CAS: 5307-60-8
• 化学式: C₂₃H₂₂O₆
• 分子量: 394.424
• InChiKey: UPHWJAWTGRBPAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  溴 、 robustic acid methyl ester 、 溶剂黄146 生成 alkaline earth salt of/the/ methylsulfuric acid
  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：
• 作为产物：
  描述：

  2,4-dihydroxy-3-iodo-6,4'-dimethoxydeoxybenzoin 在 sodium hydroxide 、 碳酸氢钠 、 potassium carbonate 、 N,N-二甲基苯胺 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 46.0h， 生成 robustic acid methyl ester
  参考文献：
  名称：

  线性3-苯基吡喃香豆素的合成：鲁棒素，鲁棒酸及其甲基醚的合成

  摘要：

  线性3-苯基吡喃香豆素，即。，健壮素（5b; R 4 = H），其甲基醚（5b; R 4 = Me），健壮酸（5c; R 4 = H），其甲基醚（5c; R 4 = Me），4-甲氧基-从相应的7-（1,1-二甲基丙-2-炔氧基）-香豆素衍生物开始合成了3-苯基黄嘌呤（5a; R 4 = H）及其甲基醚（5a; R 4 = Me）。 8位位置被易引入和可移动的基团（如碘）所封闭。后续步骤包括在NN中加热丙-2-炔基醚-二甲基苯胺，其导致环化为线性吡喃香豆素，伴随着碘的去除以及4-位甲氧基的部分去甲基化。获得的化合物与天然样品相同，并且与相应的角异构体的真实样品不同。

  DOI：

  10.1039/p19810001697

文献信息

• A pyrano-isoflavone from seeds of Milletia thonningii
  作者：E.Martinez Olivares、W. Lwande、F.Delle Monache、G.B. Marini Bettolo

  DOI：10.1016/s0031-9422(82)85056-5

  日期：1982.1

  Abstract Extraction of the seeds of Milletia thonningii gave alpinumisoflavone, its monomethyl and dimethyl derivatives, robustic acid and a new pyrano-isoflavone. The structure of the latter was established by chemical transformation and spectroscopic means.

  摘要 提取鸡血藤种子得到高山杉木异黄酮、其单甲基和二甲基衍生物、粗野酸和一种新的吡喃异黄酮。后者的结构是通过化学转化和光谱手段确定的。
• Rao; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1946, # 24, p. 465,469, 470
  作者：Rao、Seshadri

  DOI：——

  日期：——
• 30. The active principles of leguminous fish-poison plants. Part VI. Robustic acid
  作者：Stanley H. Harper

  DOI：10.1039/jr9420000181

  日期：——
• 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.