芥子醇 | 537-33-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 芥子醇
• 中文别名: 4-羟基-3,5-二甲氧基肉桂醇
• 英文名称: Syringenin
• 英文别名: sinapyl alcohol；4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenol；4-Hydroxy-3,5-dimethoxy-cinnamyl alcohol；4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenol
• CAS: 537-33-7
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: LZFOPEXOUVTGJS-UHFFFAOYSA-N

物化性质

• 熔点：
  61-65 °C (lit.)
• 沸点：
  384.7±37.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈（少许）、氯仿（少许）
• LogP：
  1.361 (est)
• 稳定性/保质期：

  存在于烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 安全说明：
  S26
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

制备方法与用途

Sinapyl酒精是一种具有口服活性的抗炎和抗氧化剂。它能够降低诱导型一氧化氮合酶和COX-2的表达水平。

反应信息

• 作为反应物：
  描述：

  芥子醇 在 allylphenol synthase from Larreatri dentata 、 Larrea tridentata cinnamyl alcohol acyltransferase-1 、 还原型辅酶Ⅰ 作用下， 以 aq. buffer 为溶剂， 反应 0.5h， 生成 4-丙烯基-2,6-二甲氧基苯酚
  参考文献：
  名称：

  Allyl/propenyl phenol synthases from the creosote bush and engineering production of specialty/commodity chemicals, eugenol/isoeugenol, in Escherichia coli

  摘要：

  The creosote bush (Larrea tridentata) harbors members of the monolignol acyltransferase, allylphenol synthase, and propenylphenol synthase gene families, whose products together are able to catalyze distinct regiospecific conversions of various monolignols into their corresponding allyl- and propenyl-phenols, respectively. In this study, co-expression of a monolignol acyltransferase with either substrate versatile allylphenol or propenylphenol synthases in Escherichia coli established that various monolignol substrates were efficiently converted into their corresponding allyl/propenyl phenols, as well as providing proof of concept for efficacious conversion in a bacterial platform. This capability thus potentially provides an alternate source to these important plant phytochemicals, whether for flavor/fragrance and fine chemicals, or ultimately as commodities, e.g., for renewable energy or other intermediate chemical purposes. Previous reports had indicated that specific and highly conserved amino acid residues 84 (Phe or Val) and 87 (Ile or Tyr) of two highly homologous allyl/propenyl phenol synthases (circa 96% identity) from a Clarkia species mainly dictate their distinct regiospecific catalyzed conversions to afford either allyior propenyl-phenols, respectively. However, several other allyl/propenyl phenol synthase homologs isolated by us have established that the two corresponding amino acid 84 and 87 residues are not, in fact, conserved. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.abb.2013.10.019
• 作为产物：
  描述：

  刺五加苷 在 emulsin 作用下， 生成 芥子醇
  参考文献：
  名称：

  Pauly; Strassberger, Chemische Berichte, 1929, vol. 62, p. 2279

  摘要：

  DOI：

文献信息

• 具有肝病疗效的化合物
  申请人：江苏新元素医药科技有限公司

  公开号：CN112250689B

  公开（公告）日：2022-01-18

  本发明公开了一类具有肝病疗效的化合物，它为具有通式(I)所示的化合物、光学异构体或其药学上可接受的盐，本发明的化合物可应用于肝病的治疗或预防，特别是在治疗或预防脂肪肝、肝纤维化或肝硬化的药物方面，具有良好的应用前景。
• Chemodivergent hydrogenolysis of eucalyptus lignin with Ni@ZIF-8 catalyst
  作者：Xue Liu、Helong Li、Ling-Ping Xiao、Run-Cang Sun、Guoyong Song

  DOI：10.1039/c8gc03511c

  日期：——

  Chemodivergent hydrogenolysis of eucalyptus biomass leading to 4-propanol- or 4-propyl-substituted phenols, together with a well-preserved carbohydrate component, was achieved by using Ni@ZIF-8 catalyst.

  通过使用Ni@ZIF-8催化剂，实现了对桉树木质素的化学多样性氢解，产生了4-丙醇或4-丙基取代的酚类化合物，同时保留了良好的碳水化合物组分。

• Non-plasmonic Ni nanoparticles catalyzed visible light selective hydrogenolysis of aryl ethers in lignin under mild conditions
  作者：Peifeng Li、Yixuan Ouyang、Gang Xiao、Yilin Zhao、Sarina Sarina、Jan Baeyens、Haijia Su、Huai-Yong Zhu

  DOI：10.1039/d1gc01953h

  日期：——

  solar-to-chemical conversion. We report a novel photocatalysis process for the selective hydrogenolysis of aryl ethers in lignin on a heterogeneous catalyst of non-precious Ni nanoparticles supported on ZrO2. Three aryl ether bonds in lignin were successfully cleaved under mild conditions with excellent conversion and good to excellent selectivity under visible light irradiation. We also used solar irradiation to

  广泛用于热催化的多功能 VIII 族金属的光驱动催化在太阳能到化学转化方面具有巨大潜力。我们报告了一种新的光催化工艺，用于在 ZrO 2上负载的非贵镍纳米颗粒的多相催化剂上选择性氢解木质素中的芳基醚. 木质素中的三个芳基醚键在温和条件下成功裂解，在可见光照射下具有优异的转化率和良好的选择性。我们还使用太阳辐射来证明总能耗显着降低。光照射激发了 Ni 纳米颗粒中的带间跃迁，由此产生的高能电子增强了芳醚的还原裂解活性。其应用潜力通过脱碱性木质素的解聚得到9.84wt%的总单体产率来说明，其中香草醛、愈创木酚和夹竹桃素作为三种主要产物。
• The synthesis and analysis of advanced lignin model polymers
  作者：C. S. Lancefield、N. J. Westwood

  DOI：10.1039/c5gc01334h

  日期：——

  Advanced lignin model polymers have been synthesised to aid in the development of new methods for lignin valorisation.

  高级木质素模型聚合物已经合成，以帮助开发木质素增值的新方法。
• Improved Pd/Ru metal supported graphene oxide nano-catalysts for hydrodeoxygenation (HDO) of vanillyl alcohol, vanillin and lignin
  作者：Shalini Arora、Neeraj Gupta、Vasundhara Singh

  DOI：10.1039/d0gc00052c

  日期：——

  Ru@GO and Pd/Ru@GO as hydrodeoxygenation (HDO) catalysts, forming p-creosol from vanillin, vanillyl alcohol and lignin after photo-catalytic fragmentation under mild conditions.

  Ru@GO和Pd/Ru@GO作为水脱氧（HDO）催化剂，在温和条件下光催化分解后，从香草醛、香草醇和木质素形成p-甲酚。