(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid 6′’-methyl ester | 1186016-30-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid 6′’-methyl ester
• 英文别名: 3β-O-[β-D-(6-methyl)-glucuronopyranosyl-(1->2)-β-D-glucuronopyranosyl]-glycyrrhetic acid；glycyrrhizic acid 6''-methyl ester；Glycyrrhizin-6 inverted exclamation marka inverted exclamation marka-methylester；(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-3,4-dihydroxy-5-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxycarbonyloxan-2-yl]oxyoxane-2-carboxylic acid
• CAS: 1186016-30-7
• 化学式: C₄₃H₆₄O₁₆
• 分子量: 836.972
• InChiKey: JENBECQUKVEUTQ-ILVQQCHOSA-N

物化性质

• 沸点：
  934.0±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  59
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  256
• 氢给体数：
  7
• 氢受体数：
  16

制备方法与用途

Glycyrrhizin-6′′-methylester（化合物22）是一种从甘草根中分离得到的甘草皂苷。它能够参与葡萄糖醛酸甲酯的生成，赋予甜味和甘草特有的风味，但没有苦味。这表明糖苷中的锥形结构结合在葡萄糖醛酸上的游离羧基对于天然甜味和甘草味道至关重要。

反应信息

• 作为产物：
  描述：

  甲醇 、 (3beta,20beta)-20-羧基-11-氧代-30-去甲齐墩果-12-烯-3-基 2-O-beta-D-吡喃葡糖基-beta-D-吡喃葡糖苷酸 在 乙酰氯 作用下， 以11%的产率得到(3β,20β)-20-carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-β-D-glucopyranuronosyl-β-D-glucopyranosiduronic acid 6′-methylester
  参考文献：
  名称：

  Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems

  摘要：

  Immunostimulatory saponin based colloidal antigen delivery systems show promise as adjuvants for subunit vaccines. For this reason, allyl oleanolate was glycosylated at the 3-position using trichloroacetimidate donors to give monodesmodic saponins following deprotection. Bisdesmodic saponins were synthesized by double glycosylation at the 3- and 28-positions of oleanolic acid. When formulated together with cholesterol and phospholipids, ring-like, helical and rod-like nanostructures were formed depending on the saponin concentrations used. As an indication of adjuvant activity, the ability of these formulations, and the saponins by themselves, to induce dendritic cell maturation was measured, but no significant activity was observed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.043