2-phenylethyl d-rutinoside | 88510-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenylethyl d-rutinoside
• 英文别名: 2-phenylethyl rutinoside；phenethyl rutinoside；phenylethyl rutinoside；phenethyl D-rutinoside；phenylethyl (6-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside；phenethyl O-rutinoside；beta-Phenylethanol beta-D-rutinoside；(2S,3R,4R,5R,6R)-2-methyl-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2-phenylethoxy)oxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 88510-08-1
• 化学式: C₂₀H₃₀O₁₀
• 分子量: 430.452
• InChiKey: OKUGUNDXBGUFPA-OCGSKHJZSA-N

物化性质

• 沸点：
  658.9±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-phenylethyl d-rutinoside 在 乙醇 、 α-rhamnosyl-β-glucosidase 作用下， 生成 6-O-(6-脱氧-alpha-L-甘露糖基)-beta-D-葡萄糖 、 苯乙醇
  参考文献：
  名称：

  α-Rhamnosyl-β-glucosidase-Catalyzed Reactions for Analysis and Biotransformations of Plant-Based Foods

  摘要：

  Most aroma compounds exist in vegetal tissues as disaccharide conjugates, rutinose being an abundant sugar moiety in grapes. The availability of aroma precursors would facilitate analytical analysis of plant-based foods. The diglycosidase alpha-rhamnosyl-beta-glucosidase from Acremonium sp. DSM 24697 efficiently transglycosylated the rutinose moiety from hesperidin to 2-phenylethanol, geraniol, and nerol in an aqueous-organic biphasic system. 2-Phenethyl rutinoside was synthesized up to millimolar level with an 80% conversion regarding the donor hesperidin. The hydrolysis of the synthesized aroma precursors was not detected in an aqueous medium. However, in the presence of ethanol as a sugar acceptor, the enzyme was able to transfer the disaccharide residue forming the alkyl-rutinoside. The aroma precursors were significantly hydrolyzed (up to 3-4% in 2 h at 30 degrees C), which indicated the potential use of the enzyme for biotechnological applications, for example, in aroma modulation of fermented foods.

  DOI：

  10.1021/jf202412e
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranosyl trichloracetamide 在 三氟化硼乙醚 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 2.0h， 生成 2-phenylethyl d-rutinoside
  参考文献：
  名称：

  Synthesis and n.m.r. spectral properties of grape monoterpenyl glycosides

  摘要：

  DOI：

  10.1016/0008-6215(90)80004-m

文献信息

• Chemoenzymatic Synthesis of Naturally Occurring Phenethyl (1→6)-β-D-Glucopyranosides
  作者：Hiroyuki Akita、Eiji Kawahara、Miho Nishiuchi、Mikio Fujii、Keisuke Kato、Yoshiteru Ida

  DOI：10.3987/com-05-10383

  日期：——
• VOIRIN, STEPHANE;BAUMES, RAYMOND;BAYONOVE, CLAUDE;MBAIRAROUA, OUBADJIM;TA+, CARBOHYDR. RES., 207,(1990) N, C. 39-56
  作者：VOIRIN, STEPHANE、BAUMES, RAYMOND、BAYONOVE, CLAUDE、MBAIRAROUA, OUBADJIM、TA+

  DOI：——

  日期：——
• Synthesis and n.m.r. spectral properties of grape monoterpenyl glycosides
  作者：Ste´phane Voirin、Raymond Baumes、Claude Bayonove、Oubadjim M'Bairaroua、Claude Tapiero

  DOI：10.1016/0008-6215(90)80004-m

  日期：1990.10
• α-Rhamnosyl-β-glucosidase-Catalyzed Reactions for Analysis and Biotransformations of Plant-Based Foods
  作者：Marisol Minig、Laura S. Mazzaferro、Rosa Erra-Balsells、Gabriela Petroselli、Javier D. Breccia

  DOI：10.1021/jf202412e

  日期：2011.10.26

  Most aroma compounds exist in vegetal tissues as disaccharide conjugates, rutinose being an abundant sugar moiety in grapes. The availability of aroma precursors would facilitate analytical analysis of plant-based foods. The diglycosidase alpha-rhamnosyl-beta-glucosidase from Acremonium sp. DSM 24697 efficiently transglycosylated the rutinose moiety from hesperidin to 2-phenylethanol, geraniol, and nerol in an aqueous-organic biphasic system. 2-Phenethyl rutinoside was synthesized up to millimolar level with an 80% conversion regarding the donor hesperidin. The hydrolysis of the synthesized aroma precursors was not detected in an aqueous medium. However, in the presence of ethanol as a sugar acceptor, the enzyme was able to transfer the disaccharide residue forming the alkyl-rutinoside. The aroma precursors were significantly hydrolyzed (up to 3-4% in 2 h at 30 degrees C), which indicated the potential use of the enzyme for biotechnological applications, for example, in aroma modulation of fermented foods.