undulatoside A | 58108-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: undulatoside A
• 英文别名: 7-O-β-D-glucosylnoreugenin；5-hydroxy-2-methyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 58108-99-9
• 化学式: C₁₆H₁₈O₉
• 分子量: 354.314
• InChiKey: BYYDEEAJCDGLER-YMILTQATSA-N

物化性质

• 熔点：
  235-236 °C
• 沸点：
  668.6±55.0 °C(Predicted)
• 密度：
  1.606±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  undulatoside A 在 三乙烯二胺 、 4-二甲氨基吡啶 、 氯化铋 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 7-O-[2,3,4-tri-O-acetyl-α-L-rhamnosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranosyl]-5-hydroxy-2-methylchromone
  参考文献：
  名称：

  Concise Synthesis of 5-Methoxy-6-hydroxy-2-methylchromone-7-O- and 5-Hydroxy-2-methylchromone-7-O-rutinosides. Investigation of Their Cytotoxic Activities against Several Human Tumor Cell Lines

  摘要：

  The synthesis of two novel 2-methylchromone-7-O-rutinosides is reported, and the in vitro biological activities of these compounds and their synthetic precursors have been investigated on the basis of their cytotoxicity against several human tumor cell lines. The synthesis features early stage assembly of the acidic labile glycosidic bond between sugar and 2-methylchromone aglycon under phase transfer catalyzed glycosidation conditions, whereas all the other standard glycosylation conditions specific to a wide array of rutinosyl donors bearing different anomeric leaving groups (e.g., SPh, OC(NH)CCl3, Br, OH groups) failed to furnish any detectable products.

  DOI：

  10.1021/jo102325s
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 吡啶 、 sodium methylate 、 乙酸酐 、 甲基三辛基氯化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 20.0h， 生成 undulatoside A
  参考文献：
  名称：

  Concise Synthesis of 5-Methoxy-6-hydroxy-2-methylchromone-7-O- and 5-Hydroxy-2-methylchromone-7-O-rutinosides. Investigation of Their Cytotoxic Activities against Several Human Tumor Cell Lines

  摘要：

  The synthesis of two novel 2-methylchromone-7-O-rutinosides is reported, and the in vitro biological activities of these compounds and their synthetic precursors have been investigated on the basis of their cytotoxicity against several human tumor cell lines. The synthesis features early stage assembly of the acidic labile glycosidic bond between sugar and 2-methylchromone aglycon under phase transfer catalyzed glycosidation conditions, whereas all the other standard glycosylation conditions specific to a wide array of rutinosyl donors bearing different anomeric leaving groups (e.g., SPh, OC(NH)CCl3, Br, OH groups) failed to furnish any detectable products.

  DOI：

  10.1021/jo102325s

文献信息

• Three chromones from bulbs of Pancratium biflorum
  作者：Shibnath Ghosal、Shripati Singh、Mahendra P. Bhagat、Yatendra Kumar

  DOI：10.1016/0031-9422(80)85074-6

  日期：1980.1

  Abstract Two polyoxygenated chromones, 5,7-dihydroxy-2-methylchromone (1) and 5,6-dihydroxy-7- methoxy-2-methylchromone(2), and a glucosyloxychromone, 7

  摘要 两种多氧化色酮，5,7-二羟基-2-甲基色酮 (1) 和 5,6-二羟基-7-甲氧基-2-甲基色酮 (2)，以及一种葡糖氧基色酮，7
• Noreugenin glycoside derivatives
  申请人：Universitaet Hamburg

  公开号：US10722441B2

  公开（公告）日：2020-07-28

  A use of noreugenin glycoside derivatives of formulas I, II and III as a self-tanning substance or to increase the synthesis of melanin, improve melanin transport and/or improve the distribution of melanin in suprabasal layers, preparations containing noreugenin glycoside derivatives of formulas I, II and III, and noreugenin glycoside derivatives of formulas I, II and III.

  一种将式 I、II 和 III 的去甲山豆根苷衍生物用作自黑物质或增加黑色素合成、改善黑色素运输和/或改善黑色素在基底层上的分布的用途，含有式 I、II 和 III 的去甲山豆根苷衍生物的制剂，以及式 I、II 和 III 的去甲山豆根苷衍生物。
• Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus
  作者：Zalihe Hakki、Benjamin Cao、Allison M. Heskes、Jason Q.D. Goodger、Ian E. Woodrow、Spencer J. Williams

  DOI：10.1016/j.carres.2010.07.029

  日期：2010.9

  Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K-1 and K-2. Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena. (C) 2010 Elsevier Ltd. All rights reserved.
• Dayal, Rameshwar; Dobhal, P. C., Journal of the Indian Chemical Society, 1991, vol. 68, # 8, p. 478 - 479
  作者：Dayal, Rameshwar、Dobhal, P. C.

  DOI：——

  日期：——
• NOREUGENIN-GLYKOSID-DERIVATE
  申请人：Universität Hamburg

  公开号：EP3402576B1

  公开（公告）日：2021-07-28