(E)-5-(4-hydroxy-3-methylstyryl)benzene-1,3-diol | 1006685-23-9

• 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: (E)-5-(4-hydroxy-3-methylstyryl)benzene-1,3-diol
• 英文别名: 3'-methylresveratrol；5-[(E)-2-(4-hydroxy-3-methylphenyl)ethenyl]benzene-1,3-diol
• CAS: 1006685-23-9
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: MIFJPQBYDMDXRO-NSCUHMNNSA-N

物化性质

• 沸点：
  450.7±14.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-(4-hydroxy-3-methylstyryl)benzene-1,3-diol 、 加尔万氧基自由基 以 乙腈 为溶剂， 生成 2,6-二叔丁基-4-(3,5-二叔丁基-4-羟基苯亚甲基)-2,5-环己二烯-1-酮
  参考文献：
  名称：

  Effect of Methyl Substitution on the Antioxidative Property and Genotoxicity of Resveratrol

  摘要：

  Resveratrol (trans- 3,4 ',5-trihydroxystilbene) is a natural phytoalexin with various biological activities including inhibition of lipid peroxidation and free radical scavenging properties. In addition to its beneficial effects, resveratrol also has significant genotoxicity that leads to a high frequency of chromosome aberration together with micronucleus and sister chromatid exchanges. To enhance the radical scavenging activities and to reduce the genotoxicity of resveratrol, we designed 4 '-methyl resveratrol analogues where a methyl group was introduced at the ortho position relative to the 4 '-hydroxy group, which is responsible for both antioxidative activities and genotoxicity of resveratrol. These synthesized methyl analogues of resveratrol showed increased antioxidative activities against galvinoxyl radical as an oxyl radical species. Furthermore, the methyl analogues also surprisingly showed reduced in vitro genotoxicities, suggesting that methyl substitution may improve resveratrol efficacy.

  DOI：

  10.1021/tx7003008
• 作为产物：
  描述：

  (E)-1-(benzyloxy)-4-[3,5-bis(benzyloxy)styryl]-2-methylbenzene 在 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以50.4%的产率得到(E)-5-(4-hydroxy-3-methylstyryl)benzene-1,3-diol
  参考文献：
  名称：

  Effect of Methyl Substitution on the Antioxidative Property and Genotoxicity of Resveratrol

  摘要：

  Resveratrol (trans- 3,4 ',5-trihydroxystilbene) is a natural phytoalexin with various biological activities including inhibition of lipid peroxidation and free radical scavenging properties. In addition to its beneficial effects, resveratrol also has significant genotoxicity that leads to a high frequency of chromosome aberration together with micronucleus and sister chromatid exchanges. To enhance the radical scavenging activities and to reduce the genotoxicity of resveratrol, we designed 4 '-methyl resveratrol analogues where a methyl group was introduced at the ortho position relative to the 4 '-hydroxy group, which is responsible for both antioxidative activities and genotoxicity of resveratrol. These synthesized methyl analogues of resveratrol showed increased antioxidative activities against galvinoxyl radical as an oxyl radical species. Furthermore, the methyl analogues also surprisingly showed reduced in vitro genotoxicities, suggesting that methyl substitution may improve resveratrol efficacy.

  DOI：

  10.1021/tx7003008

文献信息

• SELECTIVE INHIBITION OF C4-PEP CARBOXYLASES
  申请人：HEINRICH HEINE UNIVERSITÄT DÜSSELDORF

  公开号：US20150366206A1

  公开（公告）日：2015-12-24

  The present invention relates to the use of a compound, a salt or solvate thereof as C4 plant selective herbicide wherein said compound has a structure according to formula (I) wherein A is a cyclic alkyl, aryl, heterocycloalkyl, or heteroaryl group, and B is a cyclic alkyl, aryl, heterocycloalkyl, or heteroaryl group, and wherein R 1 , R 2 , R 3 , R 4 and R 5 are, independently of each other H or an alkyl group, and wherein integer i is 0 or 1, preferably 1, and the bond (a) is a single or double bond, and wherein in case (a) is a double bond, n is 0 and X is O or S, and wherein in case (a) is a single bond n is 1, and X is H or an alkyl group, and wherein the bond (b) is a single or double bond, and wherein in case (b) is a double bond, m and p are 0, and wherein in case (b) is a single bond m and p are both 1, and/or according to formula (II) including tautomeric structures thereof, wherein R 01 and R 02 are independently of each other selected from the group consisting of H, OH, carboxylic acid, ester, alkyl, alkoxy and halogen, wherein Y 1 is selected from the group consisting of (S(=0)2), S(=0)) and (C(═O)), and wherein Y 2 is O, and wherein r is 0 or 1 and wherein in case r is 0, q and s are 1, and wherein in case r is 1, q and s are 0, and wherein R 01 , R 02 , R 04 , R 05 , R 06 , R 07 , R 04# , R 05# , R 06# , R 07# , R 09 , R 010 , R 011 and R 012 are independently of each other selected from the group consisting of H, OH, —SO3H, carboxylic acid, ester, alkyl, alkoxy and halogen, said compound being capable of binding to the malate binding site comprised by a phosphoenolpyruvate carboxylase from a C4 plant, thereby inhibiting said phosphoenolpyruvate carboxylase.
• [EN] METHOD OF TREATING AGE-RELATED MACULAR DEGENERATION<br/>[FR] MÉTHODE DE TRAITEMENT DE LA DÉGÉNÉRESCENCE MACULAIRE LIÉE À L'ÂGE
  申请人：ZHUHAI QIWEI BIO TECH LTD

  公开号：WO2020113373A1

  公开（公告）日：2020-06-11

  Provided herein are compounds/compositions that are useful for killing or inhibiting the growth of a microorganism, such as Bacillus megaterium. Also provided herein are methods of using the compounds/compositions for treating infections with a microorganism, such as Bacillus megaterium and for treating or preventing diseases or disorders associated with such infections, such as AMD.
• Effect of Methyl Substitution on the Antioxidative Property and Genotoxicity of Resveratrol
  作者：Kiyoshi Fukuhara、Ikuo Nakanishi、Atsuko Matsuoka、Tomohiro Matsumura、Sachiko Honda、Mikiko Hayashi、Toshihiko Ozawa、Naoki Miyata、Shinichi Saito、Nobuo Ikota、Haruhiro Okuda

  DOI：10.1021/tx7003008

  日期：2008.2.1

  Resveratrol (trans- 3,4 ',5-trihydroxystilbene) is a natural phytoalexin with various biological activities including inhibition of lipid peroxidation and free radical scavenging properties. In addition to its beneficial effects, resveratrol also has significant genotoxicity that leads to a high frequency of chromosome aberration together with micronucleus and sister chromatid exchanges. To enhance the radical scavenging activities and to reduce the genotoxicity of resveratrol, we designed 4 '-methyl resveratrol analogues where a methyl group was introduced at the ortho position relative to the 4 '-hydroxy group, which is responsible for both antioxidative activities and genotoxicity of resveratrol. These synthesized methyl analogues of resveratrol showed increased antioxidative activities against galvinoxyl radical as an oxyl radical species. Furthermore, the methyl analogues also surprisingly showed reduced in vitro genotoxicities, suggesting that methyl substitution may improve resveratrol efficacy.