(E)-3,4-dihydroxy-5-methoxycinnamic acid methyl ester | 123692-72-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3,4-dihydroxy-5-methoxycinnamic acid methyl ester
• 英文别名: methyl 5-hydroxyferulate；4,5-Dihydroxy-3-methoxy-zimtsaeure-methylester, (3-Methoxy-kaffeesaeure-methylester)；3-Methoxy-kaffeesaeure-methylester；3,4-Dihydroxy-5-methoxy-trans-cinnamic acid methyl ester；methyl (E)-3-(3,4-dihydroxy-5-methoxyphenyl)prop-2-enoate
• CAS: 123692-72-8
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: AAKKARXDZDUXHU-ONEGZZNKSA-N

物化性质

• 沸点：
  405.1±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (E)-3,4-dihydroxy-5-methoxycinnamic acid methyl ester 在 palladium/alumina 氢气 作用下， 生成 4,5-Dihydroxy-3-methoxy-hydrozimtsaeure-methylester (3-Methoxy-hydrokaffeesaeure-methylester)
  参考文献：
  名称：

  Horner,L. et al., Chemische Berichte, 1965, vol. 98, p. 1233 - 1245

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基丙二酸氢 、 3,4-二羟基-5-甲氧基苯甲醛 生成 (E)-3,4-dihydroxy-5-methoxycinnamic acid methyl ester
  参考文献：
  名称：

  Horner,L. et al., Chemische Berichte, 1965, vol. 98, p. 1233 - 1245

  摘要：

  DOI：

文献信息

• Insights into lignin primary structure and deconstruction from Arabidopsis thaliana COMT (caffeic acid O-methyl transferase) mutant Atomt1
  作者：Syed G. A. Moinuddin、Michaël Jourdes、Dhrubojyoti D. Laskar、Chanyoung Ki、Claudia L. Cardenas、Kye-Won Kim、Dianzhong Zhang、Laurence B. Davin、Norman G. Lewis

  DOI：10.1039/c004817h

  日期：——

  The Arabidopsis mutant Atomt1 lignin differs from native lignin in wild type plants, in terms of sinapyl (S) alcohol-derived substructures in fiber cell walls being substituted by 5-hydroxyconiferyl alcohol (5OHG)-derived moieties. During programmed lignin assembly, these engender formation of benzodioxane substructures due to intramolecular cyclization of their quinone methides that are transiently formed following 8-O-4′ radical-radical coupling. Thioacidolytic cleavage of the 8-O-4′ inter-unit linkages in the Atomt1 mutant, relative to the wild type, indicated that cleavable sinapyl (S) and coniferyl (G) alcohol-derived monomeric moieties were stoichiometrically reduced by a circa 2 : 1 ratio. Additionally, lignin degradative analysis resulted in release of a 5OHG–5OHG–G trimer from the Atomt1 mutant, which then underwent further cleavage. Significantly, the trimeric moiety released provides new insight into lignin primary structure: during polymer assembly, the first 5OHG moiety is linked via a C8–O–X inter-unit linkage, whereas subsequent addition of monomers apparently involves sequential addition of 5OHG and G moieties to the growing chain in a 2 : 1 overall stoichiometry. This quantification data thus provides further insight into how inter-unit linkage frequencies in native lignins are apparently conserved (or near conserved) during assembly in both instances, as well as providing additional impetus to resolve how the overall question of lignin macromolecular assembly is controlled in terms of both type of monomer addition and primary sequence.

  拟南芥突变体 Atomt1 木质素与野生型植物中的原生木质素不同，纤维细胞壁中由 sinapyl (S) 醇衍生的亚结构被 5-hydroxyconiferyl 醇 (5OHG) 衍生的分子取代。在木质素的程序化组装过程中，由于 8-O-4′ 自由基-自由基偶联后瞬时形成的醌基甲烷的分子内环化作用，这些醌基甲烷会形成苯并二恶烷亚结构。与野生型相比，Atomt1 突变体中 8-O-4′ 单元间连接的硫代酸裂解表明，可裂解的桧醇（S）和松柏醇（G）衍生的单体分子以约 2 ：1 的比例减少。此外，木质素降解分析还导致 Atomt1 突变体释放出 5OHG-5OHG-G 三聚体，然后进一步裂解。值得注意的是，释放出的三聚体提供了对木质素一级结构的新认识：在聚合物组装过程中，第一个 5OHG 分子通过 C8-O-X 单元间连接，而随后单体的添加显然涉及 5OHG 和 G 分子以 2 ：1 的总比例。因此，这些定量数据让我们进一步了解了在这两种情况下，原生木质素中的单元间连接频率是如何在组装过程中保持不变（或接近不变）的，同时也为解决木质素大分子组装的整体问题提供了更多动力，即单体添加类型和主序是如何受控的。
• Chemical Constituents of the Pericarp of<i>Platycladus orientalis</i>
  作者：Yueh-Hsiung Kuo、Wen-Chin Chen

  DOI：10.1002/jccs.199900110

  日期：1999.10

  AbstractIn previous papers, we have reported two new compounds, 15‐hydroxypinusolidic acid and platydiol, from the pericarp of Platycladus orientalis. In addition to the above compounds, the isolation and identification of twenty‐one compounds from the same source are described. Their structures were determined on the basis of spectral evidence as well as direct comparison with authentic samples. These compounds included four fatty alcohols and acids, three monolignols, one sesquiterpene, nine diterpenes, two steroids, one flavone, and one sugar. Among these, docosyl 3‐hydroxyferulate is a new compound. And docosyl trans‐ and cis‐ferulates were isolated in pure form.
• BARTHES, PASCALE;DURAN, HUBERT;GORRICHON, LILIANE, J. LABELL. COMPOUNDS AND RADIOPHARM., 29,(1991) N, C. 797-804
  作者：BARTHES, PASCALE、DURAN, HUBERT、GORRICHON, LILIANE

  DOI：——

  日期：——
• US6540997B1
  申请人：——

  公开号：US6540997B1

  公开（公告）日：2003-04-01
• Horner,L. et al., Chemische Berichte, 1965, vol. 98, p. 1233 - 1245
  作者：Horner,L. et al.

  DOI：——

  日期：——