3,5,3’,4’-四羟基-6,7-二甲氧基黄酮 | 29536-44-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3,5,3’,4’-四羟基-6,7-二甲氧基黄酮
• 中文别名: 3,5,3',4'-四羟基-6,7-二甲氧基黄酮
• 英文名称: 3′-dimethoxy-5,6,4′-trihydroxyflavon
• 英文别名: 3,5,3',4'-tetrahydroxy-6,7-dimethoxyflavone；6,7-dimethoxy-3,5,3',4'-tetrahydroxyflavone；6,7-dimethoy-3,5,3',4'-tetrahydroxylflavone；eupatoletin；eupatolitin；2-(3,4-dihydroxy-phenyl)-3,5-dihydroxy-6,7-dimethoxy-chromen-4-one；2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-6,7-dimethoxychromen-4-one
• CAS: 29536-44-5
• 化学式: C₁₇H₁₄O₈
• 分子量: 346.293
• InChiKey: WYKWHSPRHPZRCR-UHFFFAOYSA-N

物化性质

• 沸点：
  640.0±55.0 °C(Predicted)
• 密度：
  1.591±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

安全信息

• 海关编码：
  2914509090

制备方法与用途

广藿香素是从藁本广藿香中分离出的一种黄酮醇化合物。

反应信息

• 作为反应物：
  描述：

  3,5,3’,4’-四羟基-6,7-二甲氧基黄酮 生成 Eupatolitin-tetraacetat
  参考文献：
  名称：

  HORIE, TOKUNARU;KAWAMURA, YASUHIKO;TSUKAYAMA, MASAO;YOSHIZAKI, SHIRO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1216-1220

  摘要：

  DOI：
• 作为产物：
  描述：

  [2-(3,4-dihydroxyphenyl)-3-hydroxy-6,7-dimethoxy-4-oxochromen-5-yl] 4-methylbenzenesulfonate 生成 3,5,3’,4’-四羟基-6,7-二甲氧基黄酮
  参考文献：
  名称：

  HORIE, TOKUNARU;KAWAMURA, YASUHIKO;TSUKAYAMA, MASAO;YOSHIZAKI, SHIRO, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1216-1220

  摘要：

  DOI：

文献信息

• Structural elucidation of polymethoxyflavones from shift reagent proton NMR measurements
  作者：P. Joseph-Nathan、D. Abramo-Bruno、Ma.A. Torres

  DOI：10.1016/0031-9422(81)85114-x

  日期：1981.1
• Formation of UV-honey guides in Rudbeckia hirta
  作者：Karin Schlangen、Silvija Miosic、Ana Castro、Karin Freudmann、Maria Luczkiewicz、Florian Vitzthum、Wilfried Schwab、Sonja Gamsjäger、Maurizio Musso、Heidi Halbwirth

  DOI：10.1016/j.phytochem.2009.04.017

  日期：2009.5

  The UV-honey guides of Rudbeckia hirta were investigated by UV-photography, reflectance spectroscopy, LC-MS analysis and studies of the enzymes involved in the formation of the W-absorbing flavonols present in the petals. It was shown for the first time that the typical bull's eye pattern is already established at the early stages of flower anthesis on the front side of the petal surface, but is hidden to pollinators until the buds are open and the petals are unfolded. The rear side of the petals remains W-reflecting during the whole flower anthesis. Studies on the local distribution of 19 flavonols across the petals confirmed that the majority are concentrated in the basal part of the ray flower. However, in contrast to the earlier studies, eupatolitin 3-O-glucoside (6,7-dimethoxyquercetin 3-O-glucoside) was present in both the basal and apical parts of the petals, whereas eupatolin (6,7-dimethoxyquercetin 3-O-rhamnoside) was exclusively found in the apical parts. The enzymes involved in the formation of the flavonols in R. hirta were demonstrated for the first time. These include a rare flavonol 6-hydroxylase, which was identified as cytochrome P450-dependent monooxygenase and did not accept any methylated flavonol as substrate. All enzymes were present in the basal and apical parts of the petals, although some of them clearly showed higher activities in the basal part. This indicates that the local accumulation of flavonols in R. hirta is not achieved by a locally restricted presence of the enzymes involved in flavonol formation. (C) 2009 Elsevier Ltd. All rights reserved.
• Cisowski, W.; Dembinska-Migas, W.; Luczkiewicz, M., Polish Journal of Chemistry, 1993, vol. 67, # 5, p. 829 - 836
  作者：Cisowski, W.、Dembinska-Migas, W.、Luczkiewicz, M.

  DOI：——

  日期：——
• Flavonol 3-O-robinobiosides and 3-O-(2″-O-α-rhamnopyranosyl)-robinobiosides from Sesuvium portulacastrum
  作者：Wannaporn Disadee、Chulabhorn Mahidol、Poolsak Sahakitpichan、Somkit Sitthimonchai、Somsak Ruchirawat、Tripetch Kanchanapoom

  DOI：10.1016/j.tet.2011.04.041

  日期：2011.6

  Six new flavonol 3-O-robinobiosides and 3-O-(2 ''-O-alpha-L-rhamnopyranosyl)-robinobiosides, sesuviosides A F, were isolated from the aerial portion of Sesuvium portulacastrum together with ecdysterone, adenosine, 2'-O-methyladenosine, and L-tryptophan. The structure elucidations were based on analyses of chemical and spectroscopic data including 1D and 2D-NMR. Sesuviosides A-F and their aglycones exhibited radical scavenging activity using DPPH and ORAC assays. (C) 2011 Elsevier Ltd. All rights reserved.
• Horie, Tokunaru; Kawamura, Yasuhiko; Tsukayama, Masao, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 5, p. 1216 - 1220
  作者：Horie, Tokunaru、Kawamura, Yasuhiko、Tsukayama, Masao、Yoshizaki, Shiro

  DOI：——

  日期：——