trans-p-hydroxycinnamyl acetate | 619334-27-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-p-hydroxycinnamyl acetate
• 英文别名: trans-Coumaryl acetate；[(E)-3-(4-hydroxyphenyl)prop-2-enyl] acetate
• CAS: 619334-27-9
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: UUEPXFWSBUIUAZ-NSCUHMNNSA-N

物化性质

• 沸点：
  343.4±30.0 °C(Predicted)
• 密度：
  1.162±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-p-hydroxycinnamyl acetate 在 allylphenol synthase from Larreatri dentata 、 还原型辅酶Ⅰ 作用下， 以 aq. buffer 为溶剂， 生成 (E)-1-(4-hydroxyphenyl)propene
  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：

  acetyl-CoA 、 4-(3-羟基丙-1-烯基)苯酚 在 Larrea tridentata cinnamyl alcohol acyltransferase-1 作用下， 以 aq. buffer 为溶剂， 反应 0.5h， 生成 trans-p-hydroxycinnamyl acetate
  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

文献信息

• Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction
  作者：Daniel G. Vassão、David R. Gang、Takao Koeduka、Brenda Jackson、Eran Pichersky、Laurence B. Davin、Norman G. Lewis

  DOI：10.1039/b605407b

  日期：——

  Propenyl- and allyl-phenols, such as methylchavicol, p-anol and eugenol, have gained importance as flavoring agents and also as putative precursors in the biosynthesis of 9,9′-deoxygenated lignans, many of which have potential medicinal applications. In spite of several decades of investigation, however, the complete biosynthetic pathway to a propenyl/allylphenol had not yet been reported. We have subjected a Thai basil variety accumulating relatively large amounts of the simplest volatile allylphenol, methylchavicol, to in vivo administration of radiolabeled precursors and assays of protein preparations in vitro. Through these experiments, the biosynthesis of chavicol was shown to occur via the phenylpropanoid pathway to p-coumaryl alcohol. Various possibilities leading to deoxygenation of the latter were examined, including reduction of the side-chain double bond to form p-dihydrocoumaryl alcohol, followed by dehydration to afford chavicol, as well as formation of p-methoxycinnamyl alcohol, with further side-chain modification to afford methylchavicol. A third possibility studied was activation of the side-chain alcohol of p-coumaryl alcohol, e.g.via esterification, to form a more facile leaving group via reductive elimination. The latter was shown to be the case using p-coumaryl esters as potential substrates for a NAD(P)H-dependent reductase to afford chavicol, which is then O-methylated to afford methylchavicol.

  丙烯基和烯丙基苯酚（如甲基茶维醇、对乙醇和丁香酚）作为调味剂和 9,9′-脱氧木酚素生物合成的假定前体（其中许多具有潜在的药用价值），其重要性日益凸显。然而，尽管经过了几十年的研究，丙烯基/烯丙基酚的完整生物合成途径仍未见报道。我们对一种积累了相对大量最简单挥发性烯丙基酚（甲基芹维醇）的泰国罗勒品种进行了体内放射性标记前体给药和体外蛋白质制备试验。通过这些实验，证明了俏皮醇的生物合成是通过苯丙醇途径转化为对迷迭香醇的。研究了导致后者脱氧的各种可能性，包括还原侧链双键形成对二氢香豆醇，然后脱水生成茶维醇，以及形成对甲氧基肉桂醇，进一步修饰侧链生成甲基茶维醇。研究的第三种可能性是通过酯化等方式活化对羟基肉桂醇的侧链醇，从而通过还原消除形成更容易离开的基团。研究表明，将对香豆素酯作为 NAD(P)H 依赖性还原酶的潜在底物，可以生成茶维醇，然后将茶维醇 O-甲基化，生成甲基茶维醇。
• Biosynthesis of <i>t</i>-Anethole in Anise: Characterization of <i>t</i>-Anol/Isoeugenol Synthase and an <i>O</i>-Methyltransferase Specific for a C7-C8 Propenyl Side Chain    
  作者：Takao Koeduka、Thomas J. Baiga、Joseph P. Noel、Eran Pichersky

  DOI：10.1104/pp.108.128066

  日期：2009.1.6

  The phenylpropene t-anethole imparts the characteristic sweet aroma of anise (Pimpinella anisum, family Apiaceae) seeds and leaves. Here we report that the aerial parts of the anise plant accumulate t-anethole as the plant matures, with the highest levels of t-anethole found in fruits. Although the anise plant is covered with trichomes, t-anethole accumulates inside the leaves and not in the trichomes or the epidermal cell layer. We have obtained anise cDNA encoding t-anol/isoeugenol synthase 1 (AIS1), an NADPH-dependent enzyme that can biosynthesize t-anol and isoeugenol (the latter not found in anise) from coumaryl acetate and coniferyl acetate, respectively. In addition, we have obtained a cDNA encoding S-[methyl-14C]adenosyl-l-methionine:t-anol/isoeugenol O-methyltransferase 1 (AIMT1), an enzyme that can convert t-anol or isoeugenol to t-anethole or methylisoeugenol, respectively, via methylation of the para-OH group. The genes encoding AIS1 and AIMT1 were expressed throughout the plant and their transcript levels were highest in developing fruits. The AIS1 protein is 59% identical to petunia (Petunia hybrida) isoeugenol synthase 1 and displays apparent K  m values of 145 μ  m for coumaryl acetate and 230 μ  m for coniferyl acetate. AIMT1 prefers isoeugenol to t-anol by a factor of 2, with K  m values of 19.3 μ  m for isoeugenol and 54.5 μ  m for S-[methyl-14C]adenosyl-l-methionine. The AIMT1 protein sequence is approximately 40% identical to basil (Ocimum basilicum) and Clarkia breweri phenylpropene O-methyltransferases, but unlike these enzymes, which do not show large discrimination between substrates with isomeric propenyl side chains, AIMT1 shows a 10-fold preference for t-anol over chavicol and for isoeugenol over eugenol.

  摘要：苯丙烯基丙烯醚对茴香（小茴香，伞形科）种子和叶子具有特有的甜香气味。本文报告了小茴香植物的地上部分随着植物成熟而积累苯丙烯基丙烯醚，其中果实中含有最高水平的苯丙烯基丙烯醚。尽管小茴香植物覆盖着毛茸茸的细胞，但苯丙烯基丙烯醚积累在叶子内部而不是细胞表皮或细胞外毛茸茸的层内。我们获得了编码t-anol/isoeugenol合酶1（AIS1）的小茴香cDNA，这是一种依赖于NADPH的酶，可以从香豆酸乙酯和香柏酸乙酯中生物合成t-anol和异丁香酚（后者在小茴香中不存在）。此外，我们还获得了编码S-[甲基-14C]腺苷-l-甲硫氨酸：t-anol/isoeugenol O-甲基转移酶1（AIMT1）的cDNA，这是一种酶，可以通过对对位-OH基团的甲基化将t-anol或异丁香酚转化为t-anethole或甲基异丁香酚。编码AIS1和AIMT1的基因在整个植物中表达，它们的转录水平在发育的果实中最高。AIS1蛋白与矮牵牛（Petunia hybrida）异丁香合酶1的相似性为59％，对香豆酸乙酯和香柏酸乙酯的显性Km值分别为145μm和230μm。AIMT1更喜欢异丁香酚而不是t-anol，其对S-[甲基-14C]腺苷-l-甲硫氨酸的Km值为19.3μm，对异丁香酚的Km值为54.5μm。AIMT1蛋白序列与罗勒（Ocimum basilicum）和Clarkia breweri苯丙烯基丙烯醚O-甲基转移酶大约相似40％，但与这些酶不同的是，它们在具有异构丙烯基侧链的底物之间不显示大的区分，而AIMT1则对t-anol比chavicol更倾向于异丁香酚比丁香酚更倾向于10倍。
• Novel dihydropyridine derivatives and process for preparing the same
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0145434A2

  公开（公告）日：1985-06-19

  Dihydropyridine derivatives and salts thereof represented by the general formula, which possess excellent calcium antagonist effect, hypoten- sive effect, platelets aggregation inhibitory effect, phosphodiesterase inhibitory effect, calmodulin inhibitory effect and peroxidized lipid lowering effect, and thus dihydropyridine derivatives and salts thereof are useful as a coronary blood flow improving agent such as coronary vasodilator, hypotensive agent, prophylaxis and treating agents for thrombosis, phosphodiesterase inhibitory agent, peroxidized lipid metabolism lowering agent, anti-inflammatory agent and others.

  通式代表的二氢吡啶衍生物及其盐、 具有良好的钙拮抗剂作用、降血压作用、血小板聚集抑制作用、磷酸二酯酶抑制作用、钙调素抑制作用和过氧化脂质降低作用、因此，二氢吡啶衍生物及其盐类可用作冠状动脉血流改善剂，如冠状动脉血管扩张剂、降血压剂、血栓预防和治疗剂、磷酸二酯酶抑制剂、过氧化脂质代谢降低剂、消炎剂等。
• Compositions of Alpinia galanga or Alpinia conchigera with high content of 1'S-1'-acetoxychavicol acetate suitable for pharmaceutical processing
  申请人：Nerthus ApS

  公开号：EP2952201A1

  公开（公告）日：2015-12-09

  The present invention relates to a method for preparing a granulate composition of rhizomes from Alpinia galanga or Alpinia conchigera having a high content of 1'S-1'-acetoxychavicol acetate and low microbiological count, which is suitable for preparing orally ingestible dosage forms such as tablets or capsules.

  本发明涉及一种制备 1'S-1'-acetoxychavicol acetate（1'S-1'-乙酰氧基儿茶酚醋酸酯）含量高、微生物数量低的高良姜或高良姜根茎颗粒组合物的方法，该组合物适用于制备片剂或胶囊等口服剂型。
• Method for preparing pharmaceutical compositions of rhizomes from Alpinia galanga or Alpinia conchigera having a high content of 1′S-1′-acetoxychavicol acetate (ACA)
  申请人：NERTHUS APS

  公开号：US10603349B2

  公开（公告）日：2020-03-31

  The present invention relates to a method for preparing a granulate composition of rhizomes from Alpinia galanga or Alpinia conchigera having a high and stable content of 1′S-1′-acetoxychavicol acetate and low microbiological count, which is suitable for preparing orally ingestible dosage forms such as tablets or capsules.

  本发明涉及一种制备1′S-1′-乙酰氧基儿茶酚乙酸酯含量高且稳定、微生物数量低的高良姜或高良姜根茎颗粒组合物的方法，该组合物适用于制备片剂或胶囊等口服剂型。