Octaacetyl (apigenin 7-neohesperidosid) | 6546-65-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: Octaacetyl (apigenin 7-neohesperidosid)
• 英文别名: [(2R,3R,4S,5R,6S)-3,4-diacetyloxy-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-4-oxochromen-7-yl]oxy-5-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 6546-65-2
• 化学式: C₄₃H₄₆O₂₂
• 分子量: 914.825
• InChiKey: KKUOHNWQQZSSNY-KEVGOAAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  65
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  274
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  Octaacetyl (apigenin 7-neohesperidosid) 在 Candida antarctica lipase B (Novozymes,Novozym 435) 、 异丙醇 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 5-acetoxy-7-[hexa-O-acetyl-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-4'-methoxyflavone
  参考文献：
  名称：

  Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step

  摘要：

  Acacetin and re sveratrol 3,5-di-O-beta-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.03.001
• 作为产物：
  描述：

  柚皮苷 在 吡啶 、 碘 作用下， 以 吡啶 为溶剂， 反应 12.0h， 生成 Octaacetyl (apigenin 7-neohesperidosid)
  参考文献：
  名称：

  Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step

  摘要：

  Acacetin and re sveratrol 3,5-di-O-beta-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.03.001

文献信息

• Enhancement of the Water Solubility of Flavone Glycosides by Disruption of Molecular Planarity of the Aglycone Moiety
  作者：Guy Lewin、Alexandre Maciuk、Aurélien Moncomble、Jean-Paul Cornard

  DOI：10.1021/np300460a

  日期：2013.1.25

  Enhancement of the water solubility by disruption of molecular planarity has recently been reviewed as a feasible approach in small-molecule drug discovery programs. We applied this strategy to some natural flavone glycosides, especially diosmin, a highly insoluble citroflavonoid prescribed as an oral phlebotropic drug. Disruption of planarity at the aglycone moiety by 3-bromination or chlorination

  最近，通过破坏分子平面性来增强水溶性的方法已被认为是小分子药物发现计划中的一种可行方法。我们将此策略应用于某些天然黄酮苷，尤其是薯os皂素，这是一种高度不溶的柠檬黄酮类药物，被指定为口服降血糖药。通过3-溴化或氯化破坏糖苷配基部分的平面度，得到3-溴-和3-氯二恶英，与母体化合物相比，溶解度显着增加。
• A straightforward access to neohesperidose from naringin by acetolysis. Comparative behaviour of some flavonoid neohesperidosides and rutinosides under acetolysis
  作者：Guy Lewin

  DOI：10.1016/j.tet.2013.12.064

  日期：2014.2

  semisynthesis of neohesperidose was performed in three-steps with 43% overall yield starting from naringin, the main flavonoid of grapefruit. In addition, the behaviour of two pairs of flavonoid 7-O-rhamnoglucosides (neohesperidosides naringin and rhoifolin; rutinosides hesperidin and diosmin) under same acetolysis conditions was compared. Results demonstrated the crucial influence of the oxidation state

  分三步进行新橙皮苷的简单半合成，从柚皮中的主要类黄酮柚皮苷开始，总产率为43％。另外，比较了两对类黄酮7- O-鼠李糖苷（新橙皮苷苷柚皮苷和rhoifolin；芦丁苷橙皮苷和薯os皂苷）在相同的乙酰分解条件下的行为。结果证明了糖苷配基（黄酮或黄酮）的氧化态以及二糖部分的性质对反应过程的关键影响。
• Ilyas, Mohammad; Perveen, Mehtab; Ahmad, Syed Mohmud, Journal of the Indian Chemical Society, 2000, vol. 77, # 10, p. 497 - 498
  作者：Ilyas, Mohammad、Perveen, Mehtab、Ahmad, Syed Mohmud

  DOI：——

  日期：——