4-O-(β-D-glucopyranosyl)-trans-caffeic acid | 147511-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(β-D-glucopyranosyl)-trans-caffeic acid
• 英文别名: trans-caffeic acid 4-O-β-D-glucopyranoside；4-O-β-D-glucopyranosyl-trans-caffeic acid；(E)-4-O-(β-D-glucopyranosyl)caffeic acid；(E)-caffeic acid 4-O-β-D-glucopyranoside；4-O-(β-D-glucopyranosyl)-E-caffeic acid；4-O-β-glucopyranosyl-(E)-caffeic acid；Linocaffein；(E)-3-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
• CAS: 147511-61-3
• 化学式: C₁₅H₁₈O₉
• 分子量: 342.303
• InChiKey: OHEYCHKLBCPRLZ-VHCZEJTMSA-N

物化性质

• 沸点：
  689.2±55.0 °C(Predicted)
• 密度：
  1.625±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-O-(β-D-glucopyranosyl)-trans-caffeic acid 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 葡萄糖
  参考文献：
  名称：

  The First Cyclic Phenolic Acid Glycoside Dimer and New .ALPHA.-Tetralone and Triterpenoid Glucosides from Gentiana loureirii

  摘要：

  对 Gentiana loureirii 整个植物的进一步化学研究导致了三种新化合物的分离和表征，环状 4-O-β-<小>D-吡喃葡萄糖基咖啡酸二聚体 (1)，一种新的 α-四氢萘酮， 4-羟基-6-甲基-α-四氢萘酮4-O-β-<小>D-吡喃葡萄糖苷(2)和3β,30-二羟基-12-ursen-28-oic酸28-O- β-<小>D-吡喃葡萄糖酯 (3)，以及五种已知化合物。据我们所知，化合物1是第一个环状酚酸苷二聚体。

  DOI：

  10.1248/cpb.58.565
• 作为产物：
  描述：

  methyl 4-O-β-glucopyranosyl-(E)-caffeate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以85%的产率得到4-O-(β-D-glucopyranosyl)-trans-caffeic acid
  参考文献：
  名称：

  Chemical Synthesis of Hydroxycinnamic Acid Glucosides and Evaluation of Their Ability To Stabilize Natural Colors via Anthocyanin Copigmentation

  摘要：

  This work describes the chemical synthesis of O-aryi-beta-D-glucosides and 1 -O-beta-D-glucosyl esters of hydroxycinnamic acids. In particular, OLaryl-beta-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-beta-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl-beta-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the pi-stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.

  DOI：

  10.1021/jf071205v

文献信息

• Structure of anthocyanin from the blue petals of Phacelia campanularia and its blue flower color development
  作者：Mihoko Mori、Tadao Kondo、Kenjiro Toki、Kumi Yoshida

  DOI：10.1016/j.phytochem.2005.12.024

  日期：2006.3

  The dicaffeoyl anthocyanin, phacelianin, was isolated from blue petals of Phacelia campanularia. Its structure was determined to be 3-O-(6-O-(4'-O-(6-O-(4'-O-beta-d-glucopyranosyl-(E)-caffeoyl)-beta-d-glucopyranosyl)-(E)-caffeoyl)-beta-d-glucopyranosyl)-5-O-(6-O-malonyl-beta-d-glucopyranosyl)delphinidin. The CD of the blue petals of the phacelia showed a strong negative Cotton effect and that of the

  双咖啡酰花青素，phacelianin，是从Phacelia campanularia 的蓝色花瓣中分离出来的。其结构被确定为 3-O-(6-O-(4'-O-(6-O-(4'-O-β-d-吡喃葡萄糖基-(E)-caffeoyl)-β-d-吡喃葡萄糖基)-(E)-咖啡酰)-β-d-吡喃葡萄糖基)-5-O-(6-O-丙二酰-β-d-吡喃葡萄糖基)飞燕草素。phacelia蓝色花瓣的CD显示出强烈的负Cotton效应，有色原生质体悬浮液的CD相同，表明phacelianin的生色团可能在蓝色液泡中以逆时针堆积的方式进行分子间堆积. 在弱酸性水溶液中，phacelianin 在 CD 中显示出与花瓣相同的蓝色和负棉花效应。然而，在没有金属离子的情况下逐渐形成蓝黑色沉淀。可能需要极少量的 Al(3+) 或 Fe(3+) 来稳定蓝色溶液。Phacelianin 可能同时采取分子间和分子内堆积的形式，通
• Olinioside, 5-(4′-O-β-d-glucopyranosyl)-caffeoyloxy-5,6- dihydro-4-methyl-(2H)-pyran-2-one from Olinia usambarensis
  作者：Edward Nyandat、Emil Rwekika、Corrado Galeffi、Giovanna Palazzino、Marcello Nicoletti

  DOI：10.1016/0031-9422(93)85118-b

  日期：1993.8

  From an extract of root bark of Olinia usambarensis, which showed antifeedant activity, 5-(4'-O-beta-D-glucopyranosyl)-caffeoyloxy-5,6-dihydro-4-methyl-(2H)-pyran-2-one, named olinioside, caffeic acid, and 4-0-beta-D-glucopyranosylcaffeic acid were isolated. The structure of olinioside was assigned by chemical and spectroscopic methods.
• A tetra-acylated cyanidin 3-sophoroside-5-glucoside from the purple-violet flowers of Moricandia arvensis (L.) DC. (Brassicaceae)
  作者：Fumi Tatsuzawa、Shun Ito、Motoki Sato、Hiroki Muraoka、Kazuhisa Kato、Yoshihito Takahata、Satoshi Ogawa

  DOI：10.1016/j.phytol.2012.12.007

  日期：2013.5

  A novel tetra-acylated cyanidin 3-sophoroside-5-glucoside was isolated from the purple-violet flowers of Moricandia arvensis (L.) DC. (Family: Brassicaceae), and determined to be cyanidin 3-O-[2-O-(2-O-(4-O-(6-O-(4-O-(beta-glucopyranosyl)-trans-caffeoyl)-beta-glucopyranosyl)-trans-caffeoyl)-beta-glucopyranosyl)-6-O-(trans-caffeoyl)-beta-glucopyranoside]-5-O-[ 6-O-(malonyl)-beta-glucopyranoside] by chemical and spectroscopic methods. (C) 2013 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.
• An acylated delphinidin glycoside in the blue flowers of Evolvulus pilosus
  作者：Kenjiro Toki、Norio Saito、Kazuko Kawano、Tin Sen Lu、Atsushi Shigihara、Toshio Honda

  DOI：10.1016/s0031-9422(00)89783-6

  日期：1994.6

  A new acylated anthocyanin was isolated from the blue flowers of Evolvulus pilosus cv 'Blue Daze' as a major anthocyanin. The structure of this pigment was determined to be delphinidin 3-O-(6-O-(trans-4-O-(6-O-(trans-3-O-(beta-D-glucopyranosyl)-caffeyl)- beta-D-glucopyranosyl)-caffeyl)-beta-D-glucopyranoside)-5-O-((6-O-malonyl)-beta-D-glucopyranoside) by chemical and spectral methods.
• Helferich; Vorsatz, Journal fur praktische Chemie (Leipzig 1954), 1936, vol. <2> 145, p. 270
  作者：Helferich、Vorsatz

  DOI：——

  日期：——