D-cymarose | 89253-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-cymarose
• 英文别名: α-D-cymaropyranose；α-D-cymarose；alpha-D-Cymarose pyranose；(2S,4S,5R,6R)-4-methoxy-6-methyloxane-2,5-diol
• CAS: 89253-98-5
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: DBDJCJKVEBFXHG-JRTVQGFMSA-N

物化性质

• 沸点：
  288.7±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  D-(-)-trans-erythro-1,1-dimethoxy-3,4-epoxyhexan-5-ol 在 ion-exchange resin KU-2 、 sodium methylate 作用下， 以 水 为溶剂， 反应 16.0h， 生成 D-cymarose
  参考文献：
  名称：

  Arshava, B. M.; Raifel'd, Yu. E.; Makin, S. M., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 8.1, p. 1439 - 1445

  摘要：

  DOI：

文献信息

• Steroidal Glycosides from Roots of Cynanchum otophyllum
  作者：Xin-Xin Yang、Yong-Rui Bao、Shuai Wang、Rui-Qing Zhu、Li-Na Bao、Yu-Peng Guan、Xian-Sheng Meng

  DOI：10.1007/s10600-015-1388-3

  日期：2015.7

  Four steroids were isolated from the ethyl acetate extract of the roots of Cynanchum otophyllum. Their structures were identified as qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside (1), gagamine (2), otophylloside B (3), and caudatin (4). Compound 1 is a new steroidal glycoside, and the structures of these compounds were established on the basis of chemical and spectroscopic methods.

  从牛皮消（Cynanchum otophyllum）根部的乙酸乙酯提取物中分离得到4个甾体化合物，其结构被鉴定为：青阳参苷（qinyangshengenin-3-O-β-D-oleandropyranosyl-(1→4)-β-D-oleandropyranosyl-(1→4)-β-D-cymaropyranosyl-(1→4)-β-D-cymaropyranoside，1）、加加明（gagamine，2）、牛皮消苷B（otophylloside B，3）和牛皮消苷元（caudatin，4）。化合物1是一种新的甾体糖苷，这些化合物的结构是通过化学和光谱方法确定的。
• Bioactive C₂₁ Steroidal Glycosides from the Roots of <i>Cynanchum otophyllum</i> That Suppress the Seizure-like Locomotor Activity of Zebrafish Caused by Pentylenetetrazole
  作者：Jin-Long Li、Juan Zhou、Zhen-Hua Chen、Sheng-Ya Guo、Chun-Qi Li、Wei-Min Zhao

  DOI：10.1021/np501058b

  日期：2015.7.24

  Six new C-21 steroidal glycosides, cynotophyllosides A-F (1-6), together with 16 known compounds, were isolated from the roots of Cynanchum otophyllum. The structures of the new compounds were elucidated by spectroscopic analysis and chemical methods. The three major components, otophylloside F (15), otophylloside B (17), and rostratamine 3-O-beta-D-oleandropyranosyl-(1 beta-D-oleandropyranosyl-(1 -> 4)-beta-D-cymaropyranosyl (1 -> 4)-beta-D-cymaropyranoside), suppressed the seizure-like locomotor activity caused by pentylenetetrazole in zebrafish. Preliminary structure-activity relation studies revealed that a pregnene skeleton with a C-12 ester group (ikemaoyl > cinnamoyl > hydroxy > p-hydroxybenzoyl) and a C-3 sugar chain consisting of three 2,6-dideoxysaccharide units is essential for this suppressive activity.
• Steroidal glycosides with anti-tumor activity from the roots of<i>Cynanchum wallichii</i>Wight
  作者：Gang Chen、Nan Xu、Zhi-Feng Li、Qi-Hui Zhang、Hong-Hua Wu、Yue-Hu Pei

  DOI：10.1080/10286020.2010.489821

  日期：2010.6

  Two new steroidal glycosides characterized with 2,6-dideoxypyranoses as component sugars have been isolated from roots of Cynanchum wallichii Wight. Their structure elucidation and cytotoxic activities against HL-60 and PC-3 cells are reported.