2-coumaric acid β-D-glucopyranoside | 18462-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-coumaric acid β-D-glucopyranoside
• 英文别名: melilotoside；2-(beta-d-Glucosyloxy)-cinnamic acid；3-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
• CAS: 18462-99-2
• 化学式: C₁₅H₁₈O₈
• 分子量: 326.303
• InChiKey: GVRIYIMNJGULCZ-TVKJYDDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  23
• 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：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-coumaric acid β-D-glucopyranoside 在 sodium acetate 作用下， 以 水 为溶剂， 反应 20.0h， 生成 香豆素
  参考文献：
  名称：

  Synergy Effect of Sodium Acetate and Glycosidically Bound Volatiles on the Release of Volatile Compounds from the Unscented Cut Flower (Delphinium elatum L. “Blue Bird”)

  摘要：

  Many modern floricultural varieties have lost their scent during traditional breeding programs. The factors that result in the nonscent emission of some cut flowers remain unclear. The objective of this study was to investigate whether the nonscent emission is due to one of the factors, the lack of suitable substrates (or precursors of scent compounds). Using solid-phase microextraction and dynamic headspace volatile sampling techniques, the supplement of nonvolatile compounds such as 2-coumaric acid glucoside to the unscented cut flower such as Delphinium elatum L. "Blue Bird" enhanced the emission of scent from the flower, which was sufficient for detection by the human olfaction. Interestingly, compared with feeding with each compound, the combination of sodium acetate and 2-coumaric acid glucoside showed the synergy effect on enhancement of coumarin, a cherry leaf-like scent emission from the flower, which is due to one of factors that sodium acetate enhanced the activity of beta-glucosidase being involved in the formation of the scent compound. These results suggest that some enzymes responsible for the formation of floral scents indeed occur in the unscented flowers such as Delphinium elatum L. "Blue Bird", and the non- or low-scent emission of the flowers are due to the lack of suitable substrates.

  DOI：

  10.1021/jf901176m
• 作为产物：
  描述：

  在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以57.8%的产率得到2-coumaric acid β-D-glucopyranoside
  参考文献：
  名称：

  Synergy Effect of Sodium Acetate and Glycosidically Bound Volatiles on the Release of Volatile Compounds from the Unscented Cut Flower (Delphinium elatum L. “Blue Bird”)

  摘要：

  Many modern floricultural varieties have lost their scent during traditional breeding programs. The factors that result in the nonscent emission of some cut flowers remain unclear. The objective of this study was to investigate whether the nonscent emission is due to one of the factors, the lack of suitable substrates (or precursors of scent compounds). Using solid-phase microextraction and dynamic headspace volatile sampling techniques, the supplement of nonvolatile compounds such as 2-coumaric acid glucoside to the unscented cut flower such as Delphinium elatum L. "Blue Bird" enhanced the emission of scent from the flower, which was sufficient for detection by the human olfaction. Interestingly, compared with feeding with each compound, the combination of sodium acetate and 2-coumaric acid glucoside showed the synergy effect on enhancement of coumarin, a cherry leaf-like scent emission from the flower, which is due to one of factors that sodium acetate enhanced the activity of beta-glucosidase being involved in the formation of the scent compound. These results suggest that some enzymes responsible for the formation of floral scents indeed occur in the unscented flowers such as Delphinium elatum L. "Blue Bird", and the non- or low-scent emission of the flowers are due to the lack of suitable substrates.

  DOI：

  10.1021/jf901176m

文献信息

• Synergy Effect of Sodium Acetate and Glycosidically Bound Volatiles on the Release of Volatile Compounds from the Unscented Cut Flower (<i>Delphinium elatum</i> L. “Blue Bird”)
  作者：Ziyin Yang、Sakura Endo、Aya Tanida、Kenji Kai、Naoharu Watanabe

  DOI：10.1021/jf901176m

  日期：2009.7.22

  Many modern floricultural varieties have lost their scent during traditional breeding programs. The factors that result in the nonscent emission of some cut flowers remain unclear. The objective of this study was to investigate whether the nonscent emission is due to one of the factors, the lack of suitable substrates (or precursors of scent compounds). Using solid-phase microextraction and dynamic headspace volatile sampling techniques, the supplement of nonvolatile compounds such as 2-coumaric acid glucoside to the unscented cut flower such as Delphinium elatum L. "Blue Bird" enhanced the emission of scent from the flower, which was sufficient for detection by the human olfaction. Interestingly, compared with feeding with each compound, the combination of sodium acetate and 2-coumaric acid glucoside showed the synergy effect on enhancement of coumarin, a cherry leaf-like scent emission from the flower, which is due to one of factors that sodium acetate enhanced the activity of beta-glucosidase being involved in the formation of the scent compound. These results suggest that some enzymes responsible for the formation of floral scents indeed occur in the unscented flowers such as Delphinium elatum L. "Blue Bird", and the non- or low-scent emission of the flowers are due to the lack of suitable substrates.