4-O-β-D-glucopyranosyl-(E)-ferulic acid methyl ester | 94393-06-3

• 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-(E)-ferulic acid methyl ester
• 英文别名: 4β-(D-glycosyloxy)ferulic acid methyl ester；methyl 4-β-D-glucopyranosylferulate；methyl monomethylcaffeate glucoside；glucosyl methyl ferulate；methyl (E)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoate
• CAS: 94393-06-3
• 化学式: C₁₇H₂₂O₉
• 分子量: 370.356
• InChiKey: SKZYZICLYDNXFI-WOPWHSFLSA-N

物化性质

• 沸点：
  606.3±55.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-O-β-D-glucopyranosyl-(E)-ferulic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以85%的产率得到(E)-4-羟基-3-甲氧基肉桂酸4-O-β-D-吡喃葡萄糖苷
  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
• 作为产物：
  描述：

  methyl 4-(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl ferulate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到4-O-β-D-glucopyranosyl-(E)-ferulic acid methyl ester
  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

• Studies on the chemical constituents of Lilium henryi BAKER.
  作者：HIROKO SHIMOMURA、YUTAKA SASHIDA、YOSHIHIRO MIMAKI、YOICHI IITAKA

  DOI：10.1248/cpb.36.2430

  日期：——

  New bitter phenolic glycosides and a steroid glucoside have been isolated from the fresh bulbs of Lilium Henryi. On the basis of spectroscopic data, chemical evidence and X-ray crystallographic analysis, their structures have been elucidated as (2S)-1-O-p-methoxycinnamoyl-3-O-β-D-glucopyranosylglycerol (methylregaloside A), (2S)-1-O-caffeoyl-3-O-β-D-glucopyranosylglycerol (regaloside C), 3-O-feruloyl-6'-O-(4-O-β-D-glucopyranosylferuloyl)sucrose, and (25R)-3β, 26-dihydroxy-5α-cholestane-6, 22-dione 3-O-β-D-glucopyranoside. Several known components have also been isolated and identified.

  从百合科植物百合的新鲜鳞茎中分离得到了2个新的苦味酚苷和1个甾体葡萄糖苷，通过波谱数据、化学证据及X射线单晶衍射分析确定了它们的结构，分别为：(2S)-1-O-对-甲氧基肉桂酰基-3-O-β-D-吡喃葡萄糖基甘油（甲基罗果苷A）、(2S)-1-O-咖啡酰基-3-O-β-D-吡喃葡萄糖基甘油（罗果苷C）、3-O-阿魏酰基-6'-O-(4-O-β-D-吡喃葡萄糖基阿魏酰基)蔗糖和(25R)-3β，26-二羟基-5α-胆甾烷-6，22-二酮3-O-β-D-吡喃葡萄糖苷，同时还分离并鉴定了几种已知成分。
• Abe, Fumiko; Mori, Tomojiro; Yamauchi, Tatsuo, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 8, p. 2947 - 2956
  作者：Abe, Fumiko、Mori, Tomojiro、Yamauchi, Tatsuo

  DOI：——

  日期：——
• Chemical Synthesis of Hydroxycinnamic Acid Glucosides and Evaluation of Their Ability To Stabilize Natural Colors via Anthocyanin Copigmentation
  作者：Stephanie Galland、Nathalie Mora、Maryline Abert-Vian、Njara Rakotomanomana、Olivier Dangles

  DOI：10.1021/jf071205v

  日期：2007.9.1

  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.