methyl siaresinolate | 6154-96-7

• 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: methyl siaresinolate
• 英文别名: methyl siaresinate；3β,19α-dihydroxy-olean-12-en-28-oic acid methyl ester；3β,19α-Dihydroxy-olean-12-en-28-saeure-methylester；Siaresinolsaeure-methylester；3β.19α-Dihydroxy-oleanen-(12)-saeure-(28)-methylester；3β,19α-Dihydroxy-olean-12-en-28-carbonsaeure-methylester；methyl (1S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1,10-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 6154-96-7
• 化学式: C₃₁H₅₀O₄
• 分子量: 486.736
• InChiKey: UGARKTHCZFANNF-SUXCAEKLSA-N

物化性质

• 熔点：
  183.5-185 °C
• 沸点：
  556.8±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl siaresinolate 在 吡啶 、 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 3β-acetoxy-19-oxo-olean-12-en-28-oic acid methyl ester
  参考文献：
  名称：

  Savoir,R. et al., Bulletin des Societes Chimiques Belges, 1967, vol. 76, p. 335 - 367

  摘要：

  DOI：
• 作为产物：
  描述：

  ilexoside XVI 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 methyl siaresinolate
  参考文献：
  名称：

  Triterpenoid Saponins of Aquifoliaceous Plants. V. Ilexosides XV-XIX from the Barks of Ilex crenate Thunb.

  摘要：

  从冬青属植物的鲜皮中分离得到五种新的皂苷——冬青苷XV-XIX，并通过化学和物理化学证据阐明了它们的结构。冬青苷XV-XVII是siaresinolic酸的3,28-双苷配基，而冬青苷XVIII和XIX则是pomolic酸的苷配基。

  DOI：

  10.1248/cpb.40.1990

文献信息

• Triterpenoid Saponins of Aquifoliaceous Plants. VIII. Ilexosides XXIX-XXXII from the Leaves of Ilex rotunda Thunb.
  作者：Kayoko AMIMOTO、Kazuko YOSHIKAWA、Shigenobu ARIHARA

  DOI：10.1248/cpb.40.3138

  日期：——

  From the fresh leaves of Ilex rotunda, were isolated four new saponins named ilexosides XXIX-XXXII, together with the known saponins pedunculoside, ziyu-glycoside I, suavissimoside F1 and chikusetsusaponin IVa. Their structures were established on the basis of spectral and chemical evidence.

  从冬青的嫩叶中分离得到4个新的皂苷类化合物冬青皂苷XXIX-XXXII，以及已知的皂苷类化合物柄果皂苷、紫玉盘皂苷I、甜美皂苷F1和地肤子皂苷IVa。这些化合物的结构通过光谱和化学方法得到确定。
• Two new triterpenoid glycosides from leaves of Ilex chinensis Sims.
  作者：AKIRA INADA、MARI KOBAYASHI、HIROKO MURATA、TSUTOMU NAKANISHI

  DOI：10.1248/cpb.35.841

  日期：——

  Two new triterpenoid glycosides were isolated (one of them as the methyl ester) as major components from leaves of Ilex chinensis SIMS (Aquifoliaceae). The structures of these glycosides, termed ilexoside A (1) and ilexoside B methyl ester (2a), have been established to be 3β-Ο (β-D-xylopyranosyl) siaresinolic acid and 3β-Ο (β-D-xylopyranosyl) pomolic acid methyl ester, respectively, based on chemical and spectral evidence. High-resolution 13C-nuclear magnetic resonance data for the methyl ester of 1 (1a) and 2a are also reported.

  从冬青属植物枸骨叶（冬青科）中分离得到两种新的三萜皂苷类化合物（其中一种是甲酯），它们是主要成分。根据化学和光谱数据，确定这两种化合物的结构分别为3β-Ο（β-D-木吡喃糖基）siaresinolic酸和3β-Ο（β-D-木吡喃糖基）pomolic酸甲酯，分别命名为ilexoside A（1）和ilexoside B甲酯（2a）。还报道了1的甲酯（1a）和2a的高分辨率13C-核磁共振数据。
• 104. Sapogenins. Part XV. Siaresinolic acid
  作者：Philip Bilham、George A. R. Kon、Walter C. J. Ross

  DOI：10.1039/jr9420000540

  日期：——
• Zur Kenntnis der Triterpene. (78. Mitteilung). Einf�hrung zus�tzlicher Doppelbindungen beim ?- und ?-Amyrin-Typus mit N-Brom-succinimid
  作者：L. Ruzicka、O. Jeger、J. Redel

  DOI：10.1002/hlca.19430260426

  日期：1943.6.15
• Mazusaponins I–IV, triterpene saponins from Mazus miquelii
  作者：Emiko Yaguchi、Toshio Miyase、Akira Ueno

  DOI：10.1016/0031-9422(94)00857-p

  日期：1995.5

  From whole plants of Mazus miquelii, four new saponins designated as mazusaponins I-IV and a known saponin, ilexoside VIII, were isolated and the structures of the new compounds elucidated as 3-O-alpha-L-arabinopyranosyl siaresinolic acid 28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester, 3-O-alpha-L-arabinopyranosyl pomolic acid 28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranasyl ester, 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl siaresinolic acid 28-O-beta-D-glucopyranosyl-( 1 --> 6)-beta-D-glucopyranosyl ester and 3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-alpha-L-arabinopyranoysl pomolic acid 28-O-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester, respectively, by spectroscopic data and chemical evidence.