coniferyl acetate | 79440-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: coniferyl acetate
• 英文别名: 3-(4-Hydroxy-3-methoxyphenyl)prop-2-EN-1-YL acetate；3-(4-hydroxy-3-methoxyphenyl)prop-2-enyl acetate
• CAS: 79440-81-6
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: XLZFUNZRKIQHOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  coniferyl acetate 在 propenylphenol synthase from Larrea tridentata 、 还原型辅酶Ⅰ 作用下， 以 aq. buffer 为溶剂， 生成 丁香酚
  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：

  4-乙酰氧基-3-甲氧基肉桂酸 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 乙酸肼 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 coniferyl acetate
  参考文献：
  名称：

  Preparation of monolignol γ-acetate, γ-p-hydroxycinnamate, and γ-p-hydroxybenzoate conjugates: selective deacylation of phenolic acetates with hydrazine acetate

  摘要：

  我们在这里报告了一种可靠且简便的合成方法，可以合成一系列单酚γ-p-羟基肉桂酸盐（包括p-香豆酸、香豆酸盐和咖啡酸盐）、γ-醋酸盐和γ-p-羟基苯甲酸盐结合物，许多尚未被报道过。这些化合物可能是天然木质素生物合成过程中的中间体，或是即将用于设计木质素的新单体结合物。关键在于开发了一种高选择性的酚酸酯去酰基化方法；即一种能够切割酚酸酯，同时保持敏感的单酚酯结合物不被破坏的方法。

  DOI：

  10.1039/c3ra42818d

文献信息

• GLYCOSIDE COMPOUND
  申请人：AJINOMOTO CO., INC.

  公开号：US20130288992A1

  公开（公告）日：2013-10-31

  Compounds of formula (I″) wherein: R 11 , R 12 , R 13 , R 14 and R 15 are hydrogen, hydroxyl, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkyl-carbonyloxy, or a G-O— group, and at least one of R 11 , R 12 , R 13 , R 14 and R 15 is a G-O— group, wherein G is a saccharide residue, X 1 is a single bond, or a methylene group, an ethylene group, a trimethylene group, a vinylene group or —CH═CH—CH 2 —, X 2 is —CO—O— or —O—CO—, p and q are integer ofs 0 to 7, and p+q=0 to 8, Y 1 is methylene, ethylene or an alkenylene group having a carbon number of 2 to 15 and 1 to 3 double bonds, and R 16 and R 17 are hydrogen, methyl or ethyl, or R 16 and R 17 form a C 3-6 cycloalkyl group, are useful as GLP-1 secretion promoting agents.

  式（I″）的化合物 其中： R11，R12，R13，R14和R15为氢，羟基，C1-6烷基，C1-6烷氧基，C1-6烷基羰氧基或G-O-基团，且R11，R12，R13，R14和R15中至少有一个是G-O-基团，其中G是糖残基， X1是单键，或亚甲基基团，乙烯基团，三亚甲基基团，乙烯基团或-CH=CH-CH2-， X2是-CO-O-或-O-CO-， p和q是0到7的整数，且p+q=0到8， Y1是亚甲基，乙烯基或碳数为2到15且具有1到3个双键的烯基基团，以及 R16和R17为氢，甲基或乙基，或R16和R17形成C3-6环烷基基团，可用作GLP-1分泌促进剂。
• Biomimetic Oxidation of Monolignol Acetate and <i>p</i>-Coumarate by Silver Oxide in 1,4-Dioxane
  作者：Ayana Yamashita、Takao Kishimoto、Masahiro Hamada、Noriyuki Nakajima、Daisuke Urabe

  DOI：10.1021/acs.jafc.9b07682

  日期：2020.2.19

  Lignin acylated with acetate and/or p-coumarate is common in many herbaceous plants. Herein, the biomimetic oxidation of γ-acylated monolignols with Ag2O was studied to understand the effect of γ-acyl groups on monolignol polymerization. The oxidation of sinapyl acetate gave γ-acylated and α-acylated β-O-4 dimers in 71 and 9.5% yields, respectively. The oxidation of sinapyl p-coumarate produced γ-acylated

  用乙酸盐和/或对香豆酸盐酰化的木质素在许多草本植物中很常见。在本文中，研究了用Ag2O仿生氧化γ-酰化的单木质醇，以了解γ-酰基对单木质醇聚合的影响。乙酸芥子酸酯的氧化分别以71和9.5％的产率得到γ-酰化的和α-酰化的β-O-4二聚体。芥子酸对香豆酸酯的氧化分别以53％和16％的产率产生了γ-酰化的β-O-4和γ-酰化的四氢化萘β-β二聚体。仅对-香豆酸酯中的芥子醇部分反应，并且对-香豆酸酯部分保持不变，这表明对香豆酸未结合到酰化的木质素中的木质素主链中。本研究中使用的所有γ-酰化单木酚均生成γ-酰化的β-O-4二聚体，这表明γ-酰化的单木酚充当木质素单体。
• <i>p</i> -Cymene as Solvent for Olefin Metathesis: Matching Efficiency and Sustainability
  作者：Artur V. Granato、Alexandra G. Santos、Eduardo N. dos Santos

  DOI：10.1002/cssc.201700116

  日期：2017.4.22

  The underexploited biorenewable p‐cymene is employed as a solvent for the metathesis of various substrates. p‐Cymene is a nontoxic compound that can be obtained in large amounts as a side product of the cellulose and citrus industry. For the cross‐metathesis of estragole with methyl acrylate, this solvent prevents the consecutive double‐bond isomerization of the product and affords the best yield of

  该低度生物可再生p -cymene被用作用于各种基材的复分解的溶剂。对‐Cymene是无毒的化合物，可以作为纤维素和柑橘工业的副产品大量获得。为了使雌草酮与丙烯酸甲酯进行交叉复分解，该溶剂可防止产品连续的双键异构化，并在所有测试的溶剂中提供最佳收率。对于烯烃复分解中的许多底物（包括药物前体）和p的使用，不希望的连续异构化是一个重大挑战苯丙胺类作为溶剂可能是防止这种情况的一种方法。对于这项工作中测试的三种底物，该溶剂比甲苯具有更好的复分解性能，与其他两种底物的性能相当。
• DFRC Method for Lignin Analysis. 1. New Method for β-Aryl Ether Cleavage:  Lignin Model Studies
  作者：Fachuang Lu、John Ralph

  DOI：10.1021/jf970539p

  日期：1997.12.1

  A new method for selective and efficient cleavage of arylglycerol-beta-aryl (beta-O-4) ether linkages in lignins is described and applied to several Lignin beta-ether models. The term "DFRC" was coined for derivatization followed by reductive cleavage. Derivatization, accompanied by cell wall solubilization, is accomplished with acetyl bromide (AcBr); reductive cleavage of resulting beta-bromo ethers utilizes zinc in acetic acid. Degradation monomers, 4-acetoxycinnamyl acetates, from beta-ether cleavage by the DFRC method were identified by NMR, CC-MS, and comparison of GC retention times with authentic compounds. Under the conditions used in this study, the beta-ether linkage of all models was cleaved in very high (> 92%) yield. The DFRC method produces simpler mixtures of monomers with higher yields than alternative hydrolytic methods. Because of its relative simplicity, mild conditions, and exceptional selectivity, this method should become a powerful analytical method for lignin characterization.
• Selective deacetylation of aromatic acetates by aminolysis
  作者：Per M»nsson

  DOI：10.1016/s0040-4039(00)86757-x

  日期：1982.1