2,3′,4,5′-tetramethoxystilbene | 20578-92-1

• 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: 2,3′,4,5′-tetramethoxystilbene
• 英文别名: 2',3,4',5-tetramethoxystilbene；2,4,3',5'-tetramethoxystilbene；3,5,2',4'-tetramethoxystilbene；TMS；trans-2,4,3',5'-tetramethoxy-stilbene；trans-2,4,3',5'-Tetramethoxy-stilben；1-[2-(2,4-Dimethoxyphenyl)ethenyl]-3,5-dimethoxybenzene
• CAS: 20578-92-1
• 化学式: C₁₈H₂₀O₄
• 分子量: 300.354
• InChiKey: JDBCWSHYEQUBLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  2,3′,4,5′-tetramethoxystilbene 在 碘 、 magnesium 、 碘甲烷 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 氧化白藜芦醇
  参考文献：
  名称：

  Benzylamide derivative compound attenuates the ultraviolet B-induced hyperpigmentation in the brownish guinea pig skin

  摘要：

  This study evaluated the effects of synthetic benzylamide compound I (2,6-dimethoxy-N-phenylbenzamide) on the ultraviolet B (UV B)-induced hyperpigmentation. of the skin. UV B-induced hyperpigmentation was elicited on brownish guinea pig skin according to the method reported by Hideya et al. [Arch Dermatol Res 290 (1998) 375] with minor modifications. A lightening effect was observed following the topical application of compound I on UV-stimulated hyperpigmentation. The skin returned to its original color after treatment with compound I. Fontana-Masson staining indicated that melanin level in the hyperpigmented area was significantly decreased in the compound I-treated animals. However, the number of melanocytes were not changed in the compound I-treated groups using the S-100 stain, which is an immunohistochemical method. In vitro experiments using the cultured melanoma cells showed a 31.7% inhibition of melanin production by compound 1 at 100 muM. In addition, this compound had no effect on the tyrosinase enzyme function. However, it exhibited a catalyzing effect on the dopachrome transformation into 5,6-dihydroxyindole-2-carboxylic acid. Overall, the pigment-lightening effects of the compound I may due to the dopachrome tautomerase stimulation. (C) 2003 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2003.09.045
• 作为产物：
  描述：

  [3,5-双(三氟甲基)苯基] 3,5-二甲氧基苄基硫醚 在 氢氧化钾 、 manganese(II) sulfate 、 NaHCO₃ buffer 、 四丁基溴化铵 、 双氧水 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 16.5h， 生成 2,3′,4,5′-tetramethoxystilbene
  参考文献：
  名称：

  3,5-双（三氟甲基）苯基砜在Julia-Kocienski直接烯烃化中

  摘要：

  3,5-双（三氟甲基）苯基（BTFP）砜7已用于与羰基化合物的Julia-Kocienski烯化反应中。砜7易于通过烷基化/氧化两步法从市售3,5-双（三氟甲基）苯硫酚中高产率（64-97％）制备。已经研究了金属化BTFP砜的稳定性并将其与杂芳基苯并噻唑-2-基（BT），1-苯基-1 H-四唑-5-基（PT）和1-叔丁基-1 H-四唑- -5-基（TBT）砜9 - 11不同的反应条件下。烷基BTFP砜之间的Julia-Kocienski烯烃7各种各样的醛以良好的收率和立体选择性提供相应的1,2-二取代的烯烃和二烯。可以在室温下使用KOH或在-78°C或室温下使用磷腈碱P2-Et和P4- t - Bu进行此一锅操作规程，已成功用于各种甲氧基化对苯二酚的高产率和立体选择性合成中如三甲基化白藜芦醇。Julia-Kocienski烯烃化反应的这些新反应条件也已用BT，PT和TBT砜进行了研究，但结果较差。脂族和芳族醛，酮和1

  DOI：

  10.1021/jo050852n

文献信息

• Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase
  作者：Suhee Song、Hyojin Lee、Youngeup Jin、Young Mi Ha、Sungjin Bae、Hae Young Chung、Hongsuk Suh

  DOI：10.1016/j.bmcl.2006.10.025

  日期：2007.1

  Oxyresveratrol and resveratrol, with hydroxy substituted trans-stilbene structure, exert potent inhibitory effects on cyclooxygenase, rat liver mitochondrial ATPase activity, and tyrosinase. As the isosteres of oxyresveratrol, a new family of hydroxyl substituted phenyl-naphthalenes were synthesized to show excellent inhibition of mushroom tyrosinase. Compound 10, which is isostere of resveratrol, showed IC50 value of 16.52 mu M in mushroom tyrosinase activity. As compared to this, the reference compound, resveratrol, showed IC50 value of 55.61 mu M. Compound 4, which is isostere of oxyresveratrol, showed IC50 value of 0.49 mu M. Among the other three derivatives, compound 13 showed IC50 value of 0.034 mu M. (c) 2006 Elsevier Ltd. All rights reserved.
• Mongolsuk et al., Journal of the Chemical Society, 1957, p. 2231
  作者：Mongolsuk et al.

  DOI：——

  日期：——
• The Antifungal Agent from Osage Orange Wood¹
  作者：Roderick A. Barnes、Nancy Nichols Gerber

  DOI：10.1021/ja01617a032

  日期：1955.6
• Takaoka, 1940, vol. <III> 3, p. 1,15
  作者：Takaoka

  DOI：——

  日期：——
• Takaoka, Nippon Kagaku Kaishi, 1940, vol. 61, p. 96
  作者：Takaoka

  DOI：——

  日期：——