Guaiacylglycerol-β,γ-bis-coniferyl ether | 107443-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Guaiacylglycerol-β,γ-bis-coniferyl ether
• 英文别名: Guajacylglycerin-bis-coniferylether H；4-[3-hydroxy-1,2-bis[4-(3-hydroxyprop-1-enyl)-2-methoxyphenoxy]propyl]-2-methoxyphenol
• CAS: 107443-37-8
• 化学式: C₃₀H₃₄O₉
• 分子量: 538.595
• InChiKey: RGTXPDPNPBRARZ-UHFFFAOYSA-N

物化性质

• 沸点：
  781.9±60.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  127.07
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  松柏醇 在 horseradish peroxidase type II 、 双氧水 、 Hexamethyldecyltrimethylammonium sulfate 作用下， 以 phosphate buffer 为溶剂， 反应 0.08h， 生成 Guaiacylglycerol-β,γ-bis-coniferyl ether 、 4,4'-[六氢呋喃并[3,4-c]呋喃-1,4-二基]双(2-甲氧基苯酚) 、 、 (±)-dehydrodiconiferyl alcohol
  参考文献：
  名称：

  A New In Vitro Model of Lignin Biosynthesis

  摘要：

  A strictly coordinate sequence of radical and ionic steps appears to be the mechanism by which oligolignols are generated. A synthetic lignin was produced under micellar conditions [Eq. (1)], and the beginning of the polymerization process was studied by electrospray ionization mass spectrometry. CTA=cetyltrimethylammonium ion.

  DOI：

  10.1002/(sici)1521-3773(19990503)38:9<1283::aid-anie1283>3.0.co;2-z

文献信息

• Lignin Chemistry: Biosynthetic Study and Structural Characterisation of Coniferyl Alcohol Oligomers Formed In Vitro in a Micellar Environment
  作者：Samantha Reale、Francesca Attanasio、Nicoletta Spreti、Francesco De Angelis

  DOI：10.1002/chem.200903302

  日期：2010.5.25

  generated in it, represent a closer mimicry of the natural microenvironment since an enzyme, under micellar conditions, reproduces the cell system better than in buffer alone. On the basis of the oligomers structures a new biosynthetic perspective was proposed that focused attention on a coniferyl alcohol dimeric quinone methide as the key intermediate of the reaction. A formal, strictly alternate sequence

  松柏醇木质素模型（所谓的脱氢聚合产物，DHP）是在均质条件下通过胶束化阳离子表面活性剂的存在而在水中制备的。报告了在我们的反应条件下对酶系统过氧化物酶/ H 2 O 2的活性的完整研究，直至五聚体的所有反应产物的特征均是11 H NMR光谱和ESI质谱。我们的系统以及在其中生成的分子代表了自然的微环境的近似模拟，因为在胶束条件下，酶比仅在缓冲液中能更好地复制细胞系统。在低聚物结构的基础上，提出了新的生物合成观点，该观点将注意力集中在作为反应的关键中间体的松柏油基二聚体醌甲基化物上。自由基和离子步骤的正式，严格交替的序列强调了该反应，从而生成有序的寡聚寡核苷酸结构。作为其他模型木质素的替代品，我们的木质素在低聚物单元之间的自由基偶联程度较低。这为观察到细胞壁中自由基产生的速率较低提供了更接近的生物合成情况。
• On the reactivity of the Melanocarpus albomyces laccase and formation of coniferyl alcohol dehydropolymer (DHP) in the presence of ionic liquid 1-allyl-3-methylimidazolium chloride
  作者：Maarit Lahtinen、Liisa Viikari、Pirkko Karhunen、Janne Asikkala、Kristiina Kruus、Ilkka Kilpeläinen

  DOI：10.1016/j.molcatb.2012.09.005

  日期：2013.1

  Some ionic liquids are able to dissolve wood, including lignin and lignocellulose, and thus they provide an efficient reaction media for modification of globally abundant wood-based polymers. Lignin can be modified with laccases (EC 1.10.3.2), multicopper oxidases, which selectively catalyze the oxidation of phenolic hydroxyl to the phenoxy radical in lignin by using oxygen as the co-substrate and an electron acceptor. Many enzymes, including laccases, retain their catalytic activity in the presence of ionic liquids. However, the enzyme activity is usually decreased in the presence of ionic liquids, and the most deactivating ionic liquids have been observed to be those dissolving wood most efficiently. In the present study the activity, pH optimum and catalyzed oxidation of coniferyl alcohol by the laccase from the ascomycete Melanocarpus albomyces was investigated in the ionic liquid 1-allyl-3-methyl-imidazolium chloride ([Amim]Cl), known to dissolve wood and expected to affect the laccase activity. Indeed, with an increasing concentration of [Amim]Cl, the activity of M. albomyces laccase decreased, and the pH range of the enzyme activity was narrowed. The pH optimum, using 2,6-dimethoxyphenol as the substrate, was shifted from 6.5 to 6.0 when the amount of [Amim]Cl was increased to 60% (m-%). It was also found that the inhibition of laccase with NaN3 was not as severe in the ionic liquid as in water. The insoluble fraction of the dehydropolymer (DHP) formed in the presence of [Amim]Cl had clearly higher molecular weight compared to the one formed in water. DHPs formed in the absence and presence of [Amim]Cl both contained beta-5, beta-beta, beta-O-4, alpha-C=O/beta-O-4 and alpha-O-4/beta-O-4 structures. However, in the presence of [Amim]Cl, less beta-O-4, slightly less beta-5 and more beta-beta structures were formed. (C) 2012 Elsevier B.V. All rights reserved.
• A New In Vitro Model of Lignin Biosynthesis
  作者：Francesco De Angelis、Rosario Nicoletti、Nicoletta Spreti、Franca Verì

  DOI：10.1002/(sici)1521-3773(19990503)38:9<1283::aid-anie1283>3.0.co;2-z

  日期：1999.5.3

  A strictly coordinate sequence of radical and ionic steps appears to be the mechanism by which oligolignols are generated. A synthetic lignin was produced under micellar conditions [Eq. (1)], and the beginning of the polymerization process was studied by electrospray ionization mass spectrometry. CTA=cetyltrimethylammonium ion.