3, 4-dihydroxylcinnamaldehyde | 68149-78-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 3, 4-dihydroxylcinnamaldehyde
• 英文别名: caffeoyl aldehyde；caffeoylaldehyde；caffeyl aldehyde；caffealdehyde；Caffeicaldehyd；3-(3,4-Dihydroxy-phenyl)-2-propenal；3-(3,4-dihydroxyphenyl)prop-2-enal
• CAS: 68149-78-0
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: AXMVYSVVTMKQSL-UHFFFAOYSA-N

物化性质

• 沸点：
  380.0±32.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)
• LogP：
  1.351 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3, 4-dihydroxylcinnamaldehyde 在 Plagiochasma appendiculatum alkenal double bond reductase 2 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.5h， 生成 3-(3,4-二羟基-苯基)-丙醛
  参考文献：
  名称：

  A single amino acid determines the catalytic efficiency of two alkenal double bond reductases produced by the liverwortPlagiochasma appendiculatum

  摘要：

  Alkenal double bond reductases (DBRs) catalyze the NADPH‐dependent reduction of the α,β‐unsaturated double bond of many secondary metabolites. Two alkenal double bond reductase genes PaDBR1 and PaDBR2 were isolated from the liverwort species Plagiochasma appendiculatum. Recombinant PaDBR2 protein had a higher catalytic activity than PaDBR1 with respect to the reduction of the double bond present in hydroxycinnamyl aldehydes. The residue at position 56 appeared to be responsible for this difference in enzyme activity. The functionality of a C56 to Y56 mutation in PaDBR1 was similar to that of PaDBR2. Further site‐directed mutagenesis and structural modeling suggested that the phenol ring stacking between this residue and the substrate was an important determinant of catalytic efficiency.

  DOI：

  10.1016/j.febslet.2013.07.051
• 作为产物：
  描述：

  4-propenylcatechol 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 生成 3, 4-dihydroxylcinnamaldehyde
  参考文献：
  名称：

  二氢迷幻素在减少尼古丁衍生亚硝胺酮 (NNK) 诱导的 A/J 小鼠肺 DNA 损伤中抗肺癌发生的体内构效关系

  摘要：

  有烟的地方…… ：研究了二氢迷幻素 (DHM) 对尼古丁衍生的亚硝胺酮 (NNK) 诱导的 A/J 小鼠 DNA 损伤的结构-活性关系，不仅鉴定了更有效的类似物，还开发了体内化学探针未来 DHM 预防肺癌的机制特征。

  DOI：

  10.1002/cmdc.202100727

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。
• Novel Compounds for Modulating Cell Proliferation
  申请人：Roifman M. Chaim

  公开号：US20070243612A1

  公开（公告）日：2007-10-18

  Novel styrylacrylonitrile compounds which are useful in treating a variety of cell proliferative disorders such as cancer are disclosed.

  本发明揭示了一种新型的苯乙烯腈化合物，可用于治疗多种细胞增殖性疾病，如癌症。
• Compounds for modulating cell proliferation
  申请人：Roifman M. Chaim

  公开号：US20070197660A1

  公开（公告）日：2007-08-23

  Compounds having the Formula (I) or (III) wherein R 1 , R 2 and R 3 are each independently selected from H, OH, C 1-6 alkyl, C 1-6 alkoxy, NH 2 , NH—(C 1-6 alkyl), N(C 1-6 alkyl)(C 1-6 alkyl), SH, S—C 1-6 alkyl, NO 2 , CF 3 , OCF 3 , and halo; R 4 is unsubstituted Ar or Ar substituted with 1-4 substituents independently selected from C 1-6 alkyl, C 1-6 alkoxy and halo; X is selected from (CH 2 CH 2 O) n and (CH) n , and n=1-4, salts, solvates and hydrates thereof, useful for modulating or inhibiting cell proliferation, are described.

  本发明提供具有式（I）或（III）的化合物，其中R1、R2和R3各自独立地选择自H、OH、C1-6烷基、C1-6烷氧基、NH2、NH—（C1-6烷基）、N（C1-6烷基）（C1-6烷基）、SH、S—C1-6烷基、NO2、CF3、OCF3和卤素；R4为未取代的Ar或取代了1-4个取代基的Ar，所述取代基各自独立地选择自C1-6烷基、C1-6烷氧基和卤素；X选择自（CH2CH2O）n和（CH）n，其中n=1-4，其盐、溶剂合物和水合物，可用于调节或抑制细胞增殖。
• A single amino acid determines the catalytic efficiency of two alkenal double bond reductases produced by the liverwort<i>Plagiochasma appendiculatum</i>
  作者：Yifeng Wu、Yuanheng Cai、Yi Sun、Ruixue Xu、Haina Yu、Xiaojuan Han、Hongxiang Lou、Aixia Cheng

  DOI：10.1016/j.febslet.2013.07.051

  日期：2013.9.17

  Alkenal double bond reductases (DBRs) catalyze the NADPH‐dependent reduction of the α,β‐unsaturated double bond of many secondary metabolites. Two alkenal double bond reductase genes PaDBR1 and PaDBR2 were isolated from the liverwort species Plagiochasma appendiculatum. Recombinant PaDBR2 protein had a higher catalytic activity than PaDBR1 with respect to the reduction of the double bond present in hydroxycinnamyl aldehydes. The residue at position 56 appeared to be responsible for this difference in enzyme activity. The functionality of a C56 to Y56 mutation in PaDBR1 was similar to that of PaDBR2. Further site‐directed mutagenesis and structural modeling suggested that the phenol ring stacking between this residue and the substrate was an important determinant of catalytic efficiency.
• <i>In vivo</i> Structure‐Activity Relationship of Dihydromethysticin in Reducing Nicotine‐Derived Nitrosamine Ketone (NNK)‐Induced Lung DNA Damage against Lung Carcinogenesis in A/J Mice
  作者：Santanu Hati、Qi Hu、Zhiguang Huo、Junxuan Lu、Chengguo Xing

  DOI：10.1002/cmdc.202100727

  日期：2022.4.5

  Where there‘s smoke …: The structure-activity relationship of dihydromethysticin (DHM) on nicotine-derived nitrosamine ketone (NNK)-induced DNA damage in A/J mice was investigated, which not only identified more potent analogs but also developed in vivo chemical probes for future mechanistic characterization of DHM in preventing lung carcinogenesis.

  有烟的地方…… ：研究了二氢迷幻素 (DHM) 对尼古丁衍生的亚硝胺酮 (NNK) 诱导的 A/J 小鼠 DNA 损伤的结构-活性关系，不仅鉴定了更有效的类似物，还开发了体内化学探针未来 DHM 预防肺癌的机制特征。