methyl vanillmandelate | 2911-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl vanillmandelate
• 英文别名: α-hydroxy-4-hydroxy-3-methoxybenzeneacetic acid methyl ester；alpha,4-dihydroxy-3-methoxy-benzeneacetic acid methyl ester；Mandelic acid, 4-hydroxy-3-methoxy-, methyl ester；methyl 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetate
• CAS: 2911-74-2
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: XPQNHALAUGGUJN-UHFFFAOYSA-N

物化性质

• 沸点：
  362.9±42.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)
• 保留指数：
  1709.4

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl vanillmandelate 在 吡啶 、 盐酸 、 氯化亚砜 、 sodium acetate 、 caesium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-[3-Methoxy-4-[3-(4-phenoxy-2-propylphenoxy)propoxy]phenyl]-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  5-芳基噻唑烷-2,4-二酮类作为选择性PPARγ激动剂。

  摘要：

  设计，合成了一系列含有4-苯氧基苯基侧链的5-芳基噻唑烷-2,4-二酮，并评估了其PPAR激动剂的活性。一种这样的化合物28在db / db小鼠2型糖尿病动物模型中显示出与罗格列酮相当的葡萄糖校正水平。

  DOI：

  10.1016/s0960-894x(03)00257-9
• 作为产物：
  描述：

  甲醇 、 3-甲氧基-4-羟基扁桃酸 生成 methyl vanillmandelate
  参考文献：
  名称：

  香扁桃酸和4-羟基苄醇衍生物与L-抗坏血酸的反应

  摘要：

  香草醛扁桃酸酯和L-抗坏血酸之间的相互作用产生了环戊-2-烯一衍生物，而香草醛扁桃酸甲酯与L-抗坏血酸的反应产生了2-呋喃羧酸作为主要产物。模型3-取代的4-羟基苄醇和L-抗坏血酸产生抗坏血酸型结构，其易于脱羧而得到相应的1-芳基-1-脱氧酮糖的混合物。

  DOI：

  10.1016/s0040-4020(97)00396-7

文献信息

• Rapid flow-through fractionation of biomass to preserve labile aryl ether bonds in native lignin
  作者：Hao Zhou、Jia Yun Xu、Yingjuan Fu、Haiguang Zhang、Zaiwu Yuan、Menghua Qin、Zhaojiang Wang

  DOI：10.1039/c9gc02315a

  日期：——

  dissolved lignin from the reactor in time and space, thereby preserving these labile aryl ether bonds in native lignin. The application of RFF of poplar wood with a short residence time of 2.6 min attained 75% delignification with an equivalent of the β-O-4 motif in native lignin. Structure-preserved lignins (β-O-4 retention, 75.0%–85.4%) were also harvested from wheat straw with good lignin yields (61.7%–78

  木质素是维管束植物的第二大成分，是地球上最丰富的可再生芳香族聚合物。木质素增值的吸引力在于它可以通过分馏和提质转化为高价值的芳香族化学品和生物燃料。文献已经证明，天然木质素中芳基醚键的存在是转化的关键因素，而碳水化合物优先生产工艺（例如纸浆和纤维素乙醇生产）中的常规工业木质素经过密集的冷凝，并且由于这些键而缺乏这些联系。激烈的脱木素条件。在这里，通过使用β-O-4木质素模型二聚体GG，我们揭示了GG的急剧降解以及相对稳定的中间β-O-4二聚体C 6 C的同步形成。3在72wt％的甲酸水溶液和130°C的条件下的前5分钟内，烯醇醚和甲酰化的烯醇醚适合于生物质分馏。基于这些发现，我们提出了一种简单但有效的快速流通分级分离（RFF）策略，该策略可在时间和空间上从反应器中分离出溶解的木质素，从而在天然木质素中保留这些不稳定的芳基醚键。杨木的RFF短停留时间2.6分钟的应用获得了75％的脱木质素作用
• Asthma and allergic inflammation modulators
  申请人：Fu Zice

  公开号：US20080085891A1

  公开（公告）日：2008-04-10

  Compounds, pharmaceutical compositions and methods are provided that are useful in the treatment of inflammatory and immune-related diseases and conditions. In particular, the invention provides compounds which modulate the function and/or expression of proteins involved in atopic diseases, inflammatory conditions and cancer. The subject compounds are carboxylic acid derivatives.

  本发明提供了在治疗炎症和免疫相关疾病和病况方面有用的化合物、制药组合物和方法。特别是，本发明提供了调节参与过敏性疾病、炎症病况和癌症的蛋白质的功能和/或表达的化合物。所述化合物为羧酸衍生物。
• Fragmentation of trimethylsilyl derivatives of 2-alkoxyphenols: A further violation of the ‘even-electron rule’
  作者：Dietlinde Krauss、Hans Georg Mainx、Bernhard Tauscher、Peter Bischof

  DOI：10.1002/oms.1210201005

  日期：1985.10

  AbstractThe mass spectra of trimethylsilyl (TMS) ethers of 2‐methoxyphenols show abundant [M–30]+˙ ions originating from consecutive loss of two methyl radicals. This is illustrated by comparison of the accurate mass‐measured and linked‐scan spectra of the TMS derivatives of 2‐methoxyphenol (guaiacol), 4‐hydroxy‐3‐methoxybenzaldehyde (vanillin) and 3‐(4‐hydroxy‐3‐methoxyphenyl)‐2‐propenoic acid methyl ester (ferulic acid methyl ester) with those of the TMS derivatives of phenol, 4‐hydroxybenzaldehyde, 3‐(4‐hydroxyphenyl)‐2‐propenoic acid methyl ester (p‐coumaric acid methyl ester), 3‐methoxyphenol and 4‐methoxyphenol. This distinctive ortho effect is valuable in the identification of isomeric phenolic compounds. In the spectra of the TMS derivatives of 2‐ethoxyphenol and 2‐propoxyphenol the sequential loss of two radicals is less pronounced, because elimination of the side‐chain and a methyl group with rearrangement and hydrogen migration is competitive.
• Structure–activity relationships of the ultrapotent vanilloid resiniferatoxin (RTX): The side chain benzylic methylene
  作者：Giovanni Appendino、Abdellah Ech-Chahad、Alberto Minassi、Luciano De Petrocellis、Vincenzo Di Marzo

  DOI：10.1016/j.bmcl.2009.11.035

  日期：2010.1

  The side chain benzylic methylene is a critical element for the vanilloid activity of resiniferatoxin (2a, RTX), and introduction of branching, oxygen functions, or isosteric substitution at this center proved detrimental, with a decrease of potency of 2-3 orders of magnitude compared to the natural product. Conversely, only a modest erosion of activity was observed upon a-methylation and alpha-methylenation of the side chain. Surprisingly, introduction of an iodine atom in the guaiacyl moiety of the oxygen isoster 2h led to an unexpected and remarkable (> 1000-fold) increase of potency, affording 2i, a compound that outperforms RTX in terms of vanilloid agonism and represents the first one-digit picomolar ligand of a TRP channel discovered to date. (C) 2009 Elsevier Ltd. All rights reserved.
• US7321001B2
  申请人：——

  公开号：US7321001B2

  公开（公告）日：2008-01-22