2-(3,4-二羟基苯基)-5,7-二羟基色烯正离子-3-基6-O-(羧基乙酰基)-β-D-吡喃葡萄糖苷 | 171828-62-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-(3,4-二羟基苯基)-5,7-二羟基色烯正离子-3-基6-O-(羧基乙酰基)-β-D-吡喃葡萄糖苷
• 英文名称: cyanidin 3-O-(6''-O-malonyl-β-glucopyranoside)
• 英文别名: cyanidin 3-(6''-malonyl)glucoside；Cy3malglc；Cyanidin 3-O-(6-O-malonyl-beta-D-glucoside)；3-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromenylium-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• CAS: 171828-62-9
• 化学式: C₂₄H₂₃O₁₄
• 分子量: 535.438
• InChiKey: ROQLTZUOXIQBDO-JZWLZXDTSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  225
• 氢给体数：
  8
• 氢受体数：
  13

安全信息

• WGK Germany：
  3
• 储存条件：
  存储条件：2-8°C，密封保存，干燥处避光。

反应信息

• 作为反应物：
  描述：

  2-(3,4-二羟基苯基)-5,7-二羟基色烯正离子-3-基6-O-(羧基乙酰基)-β-D-吡喃葡萄糖苷 在 盐酸 作用下， 以 水 为溶剂， 反应 48.0h， 生成 cyanidin-3-glucoside
  参考文献：
  名称：

  New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability

  摘要：

  Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications.

  DOI：

  10.1016/j.foodchem.2019.125796

文献信息

• Characterization of Anthocyanins and Pyranoanthocyanins from Blood Orange [<i>Citrus sinensis</i> (L.) Osbeck] Juice
  作者：Silke Hillebrand、Michael Schwarz、Peter Winterhalter

  DOI：10.1021/jf0487957

  日期：2004.12.1

  Anthocyanins from blood orange [Citrus sinensis (L.) Osbeck] juices were isolated and purified by means of high-speed countercurrent chromatography and preparative high-performance liquid chromatography. Structures of the pigments were then elucidated by electrospray ionization multiple mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy. The major anthocyanins of the juice were characterized

  通过高速逆流色谱法和制备型高效液相色谱法分离并纯化了血橙[Citrus sinensis（L.）Osbeck]果汁中的花色苷。然后通过电喷雾电离多重质谱和核磁共振（NMR）光谱阐明颜料的结构。果汁中主要花色苷的特征为花青素3-葡糖苷和花青素3-（6“-丙二酰葡糖苷）。此外，检测到6种次要花色苷，并将其鉴定为花青素3,5-二葡糖苷，飞燕草素3-葡糖苷，花青素3-槐糖苷。 ，delphinidin 3-（6“-丙二糖基葡糖苷），peonidin 3-（6”-丙二糖基葡糖苷）和花青素3-（6“-二草酰葡糖苷）。这是第一次报告血橙中后一种化合物的出现，连同完整的NMR光谱数据。进一步的研究表明存在四种花青素衍生的色素，这些色素是在果汁的长时间存储过程中，花青素与羟基肉桂酸之间的直接反应形成的。通过将它们的质谱和色谱性质与合成参考化合物进行比较，将这些新颖的吡喃花色素苷鉴定为花青素3-葡萄糖苷的4-
• Optimisation of extraction procedure and development of LC–DAD–MS methodology for anthocyanin analysis in anthocyanin-pigmented corn kernels
  作者：H.T. Hong、M.E. Netzel、T.J. O'Hare

  DOI：10.1016/j.foodchem.2020.126515

  日期：2020.7

  An ultra-high-performance liquid chromatography-diode array detector-mass spectrometry method was developed for characterisation and quantification of anthocyanin components in complex corn-kernel matrices. The anthocyanin profiles and total anthocyanin content (TAC) of mature seeds of five types of anthocyanin-pigmented corn were reported. Internal standard was used to validate the efficiency of extraction and optimise the liquid extraction procedure for anthocyanins. A total of eighteen anthocyanins were identified and quantified. Cyanidin-based glucosides were the major pigments of purple-pericarp sweetcorn (75.5% of TAC) and blue-aleurone maize (91.6%), while pelargonidin-based glucosides composed the main anthocyanins of reddish-purple-pericarp sweetcorn (61.1%) and cherry-aleurone maize (74.6%). Importantly, previous studies reported the presence of acetylated and succinylated anthocyanins in corn kernels; these compounds were found to be artefact pigments, generated during the extraction process. These crucial findings provide the correct anthocyanin profiles of pigmented corns, and emphasise the importance of using acidified solutions for the extraction of corn-based anthocyanins.
• New acylated cyanidin glycosides extracted from underutilized potential sources: Enzymatic synthesis, antioxidant activity and thermostability
  作者：Fernanda Fernandez-Aulis、Andrea Torres、Ernesto Sanchez-Mendoza、Luis Cruz、Arturo Navarro-Ocana

  DOI：10.1016/j.foodchem.2019.125796

  日期：2020.3

  Interest in anthocyanins has increased remarkably in recent decades, although their wider application has been hampered by instability problems. Thus, this study aimed at developing a strategy to gain access to more stable anthocyanins via enzymatic esterification. For that purpose, three cyanidin derivatives were obtained from underutilized, but easily accessible sources, and their total anthocyanin content was quantified. The purity of cyanidins obtained ranged from 40% to 88% depending on their source. Subsequently, the critical enzymatic reaction conditions were established, and the best results were found using tert-butanol as a solvent, 20 g/L of lipase B from Candida Antarctica, and vinyl cinnamate as acyl donor at ratio 250:1 (acyl donor to anthocyanin). Finally, five new acylated anthocyanin derivatives were synthesized with improved antioxidant activity and thermostability, in comparison to the cyanidin-3-glucoside, which is an advantageous feature for industrial applications.