tetraacetylroseoside | 54619-16-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tetraacetylroseoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(E,2R)-4-[(1S)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]but-3-en-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 54619-16-8
• 化学式: C₂₇H₃₈O₁₂
• 分子量: 554.592
• InChiKey: VJEKZSJRAPJYOR-YBFMDEBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tetraacetylroseoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以7 mg的产率得到长寿花糖甙
  参考文献：
  名称：

  Iridoid and other constituents of Canthium subcordatum

  摘要：

  DOI：

  10.1016/s0031-9422(00)98538-8
• 作为产物：
  描述：

  长寿花糖甙 以12 mg的产率得到tetraacetylroseoside
  参考文献：
  名称：

  Studies on the constituents of zizyphi fructus. V. Structures of glycosides of benzyl alcohol, vomifoliol and naringenin.

  摘要：

  新苷类，zizybeoside I (I) 和 II (II)，zizyvoside I (IV) 和 II (V)，以及 6, 8-di-C-glucosyl-2 (S)-naringenin 和 6, 8- 的混合物从枣子的乙醇提取物中分离出二-C-葡萄糖基-2(R)-柚皮素（化合物 A）以及伏米叶醇和玫瑰花苷。根据光谱和化学证据，新糖苷的结构被确定为苄基 β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃葡萄糖苷 (I)、苄基 β-D-吡喃葡萄糖基-(1→2) )-[β-D-吡喃葡萄糖基-(1→3)]-β-D-吡喃葡萄糖苷 (II)、vomifoliol 9-O-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖苷 (IV) , vomifoliol 9-O-β-吡喃葡萄糖基-(1→2)-[β-吡喃葡萄糖基-(1→3)]-β-吡喃葡萄糖苷 (V), 6, 8-二-C-葡萄糖基-2 (S)-柚皮素(VII)和6, 8-二-C-葡萄糖基-2(R)-柚皮素(VIII)。

  DOI：

  10.1248/cpb.29.3507

文献信息

• Iridoid and other constituents of Canthium subcordatum
  作者：Hans Achenbach、Reiner Waibel、Bernd Raffelsberger、Ivan Addae-Mensah

  DOI：10.1016/s0031-9422(00)98538-8

  日期：——
• A phenolic cinnamate dimer from Psoralea plicata
  作者：Arafa I. Hamed、Irina Springuel、Nasr A. El-Emary、Hidemichi Mitome、Yasuji Yamada

  DOI：10.1016/s0031-9422(97)00105-2

  日期：1997.7

  Caryophyllene oxide, alpha-tocopherol, Z and E-werneria chromenes, two furanocoumarins, bakuchicin and psoralen, in addition to plicatin-B, lupeol and stigmasterol, have been isolated from the hexane-soluble extract of the aerial parts of Psoralen plicata. Plicatin-A, 3-(-3-methyl-2,3-epoxybutyl)-p-coumaric acid methyl ester and a new dimer, alpha-diplicatin B, were isolated from the ethyl acetate-soluble fraction. From the butanol-soluble matter, roseoside A, daidzin, isopsoralic acid-O-gluco-pyranosyl and isovitexin were isolated. Most of these compounds have been isolated from this species for the first time, although known from other plant sources. (C) 1997 Elsevier Science Ltd.
• MIYASE, TOSHIO;UENO, AKIRA;TAKIZAWA, NOBUO;KOBAYASHI, HIROMI;OGUCHI, HIRO+, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3713-3719
  作者：MIYASE, TOSHIO、UENO, AKIRA、TAKIZAWA, NOBUO、KOBAYASHI, HIROMI、OGUCHI, HIRO+

  DOI：——

  日期：——
• Glycosidically Bound Norisoprenoids from Vitis vinifera cv. Riesling Leaves
  作者：George K. Skouroumounis、Peter Winterhalter

  DOI：10.1021/jf00041a004

  日期：1994.5

  HRGC and HRGC-MS identifications of glycosidically bound Riesling leaf constituents were achieved after extraction with MeOH, Amberlite XAD-2 adsorption, and subsequent enzymatic hydrolysis of the glycoconjugates. Among the enzymatically liberated aglycons 23 bound C-13 norisoprenoids were identified. With the aid of multilayer coil countercurrent chromatography (MLCCC) five major C-13 glycosides were purified, and their structures were elucidated by high-field NMR, i.e., the beta-D-glucopyranosides of vomifoliol, 4,5-dihydrovomifoliol, 3-hydroxy-5,6-epoxy-beta-ionone, grasshopper ketone, and 3-oxo-megastigman-9-ol. The latter glucoside with a saturated megastigmane skeleton is reported here for the first time. In addition, the P-D-glucopyranosides of benzyl alcohol and raspberry ketone have been isolated.
• Studies on the constituents of zizyphi fructus. V. Structures of glycosides of benzyl alcohol, vomifoliol and naringenin.
  作者：NOBUYUKI OKAMURA、AKIRA YAGI、ITSUO NISHIOKA

  DOI：10.1248/cpb.29.3507

  日期：——

  New glycosides, zizybeoside I (I) and II (II), zizyvoside I (IV) and II (V), and a mixture of 6, 8-di-C-glucosyl-2 (S)-naringenin and 6, 8-di-C-glucosyl-2 (R)-naringenin (compound A), together with vomifoliol and roseoside, were isolated from the ethanol extract of Zizyphi Fructus. On the basis of spectral and chemical evidence the structures of the new glycosides were determined as benzyl β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (I), benzyl β-D-glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside (II), vomifoliol 9-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (IV), vomifoliol 9-O-β-glucopyranosyl-(1→2)-[β-glucopyranosyl-(1→3)]-β-glucopyranoside (V), 6, 8-di-C-glucosyl-2 (S)-naringenin (VII) and 6, 8-di-C-glucosyl-2 (R)-naringenin (VIII).

  新苷类，zizybeoside I (I) 和 II (II)，zizyvoside I (IV) 和 II (V)，以及 6, 8-di-C-glucosyl-2 (S)-naringenin 和 6, 8- 的混合物从枣子的乙醇提取物中分离出二-C-葡萄糖基-2(R)-柚皮素（化合物 A）以及伏米叶醇和玫瑰花苷。根据光谱和化学证据，新糖苷的结构被确定为苄基 β-D-吡喃葡萄糖基-(1→2)-β-D-吡喃葡萄糖苷 (I)、苄基 β-D-吡喃葡萄糖基-(1→2) )-[β-D-吡喃葡萄糖基-(1→3)]-β-D-吡喃葡萄糖苷 (II)、vomifoliol 9-O-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃葡萄糖苷 (IV) , vomifoliol 9-O-β-吡喃葡萄糖基-(1→2)-[β-吡喃葡萄糖基-(1→3)]-β-吡喃葡萄糖苷 (V), 6, 8-二-C-葡萄糖基-2 (S)-柚皮素(VII)和6, 8-二-C-葡萄糖基-2(R)-柚皮素(VIII)。