(2S)-3-[(1-氧代十六烷基)氧基]-2-[[(9Z,12Z)-1-氧代-9,12-十八碳二烯-1-基]氧基]丙基6-O-alpha-D-吡喃半乳糖基-beta-D-吡喃半乳糖苷 | 145033-48-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: (2S)-3-[(1-氧代十六烷基)氧基]-2-[[(9Z,12Z)-1-氧代-9,12-十八碳二烯-1-基]氧基]丙基6-O-alpha-D-吡喃半乳糖基-beta-D-吡喃半乳糖苷
• 中文别名: 双半乳糖二酰甘油
• 英文名称: (2S)-1-O-hexadecanoyl-2-O-(9z,12z-octadecadienoyl)-3-O-[α-D-galactopyranosyl-(1''->6')-O-β-D-galactopyranosyl] glycerol
• 英文别名: (2S)-1-O-palmitoyl-2-O-linoleoyl-3-O-[α-D-galactopyranosyl-(1''->6')-β-D-galactopyranosyl]glycerol；Digalactosyldiacylglycerol；[(2S)-1-hexadecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropan-2-yl] (9Z,12Z)-octadeca-9,12-dienoate
• CAS: 145033-48-3
• 化学式: C₄₉H₈₈O₁₅
• 分子量: 917.229
• InChiKey: QZXMUPATKGLZAP-DXLAUQRQSA-N

物化性质

• 沸点：
  955.1±65.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  64
• 可旋转键数：
  40
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  231
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  甲醇 、 (2S)-3-[(1-氧代十六烷基)氧基]-2-[[(9Z,12Z)-1-氧代-9,12-十八碳二烯-1-基]氧基]丙基6-O-alpha-D-吡喃半乳糖基-beta-D-吡喃半乳糖苷 在 硫酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 亚油酸甲酯 、 棕榈酸甲酯
  参考文献：
  名称：

  番薯叶的新型半乳糖脂：通过液相色谱与电喷雾电离-四极杆飞行时间串联质谱联用进行表征。

  摘要：

  使用高效液相色谱和电喷雾电离-四极杆飞行时间串联质谱联用的分析方法，从番薯叶中分​​离并鉴定了十六种新型半乳糖脂和十种已知的半乳糖脂。使用这种技术，确定了脂肪酰基的结构和区域化学以及酰基链上双键的位置。通过分析一维和二维核磁共振谱来鉴定糖部分。通过气相色谱-质谱法确定了多不饱和脂肪酸双键的位置，并在某些情况下确定了它们的几何形状。这是甘薯叶中半乳糖脂的首次报道。

  DOI：

  10.1021/jf071331z
• 作为产物：
  描述：

  在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.75h， 生成 (2S)-3-[(1-氧代十六烷基)氧基]-2-[[(9Z,12Z)-1-氧代-9,12-十八碳二烯-1-基]氧基]丙基6-O-alpha-D-吡喃半乳糖基-beta-D-吡喃半乳糖苷
  参考文献：
  名称：

  Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase

  摘要：

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.013

文献信息

• Novel Galactolipids from the Leaves of Ipomoea batatas L.: Characterization by Liquid Chromatography Coupled with Electrospray Ionization–Quadrupole Time-of-Flight Tandem Mass Spectrometry
  作者：Assunta Napolitano、Virginia Carbone、Paola Saggese、Kinya Takagaki、Cosimo Pizza

  DOI：10.1021/jf071331z

  日期：2007.12.1

  Sixteen novel and ten known galactolipids have been isolated and characterized from the leaves of Ipomoea batatas L. (sweet potato) using an analytical method based on high-performance liquid chromatography coupled with electrospray ionization-quadrupole time-of-flight tandem mass spectrometry. Using this technique, the structures and regiochemistries of the fatty acyl groups and the positions of the

  使用高效液相色谱和电喷雾电离-四极杆飞行时间串联质谱联用的分析方法，从番薯叶中分​​离并鉴定了十六种新型半乳糖脂和十种已知的半乳糖脂。使用这种技术，确定了脂肪酰基的结构和区域化学以及酰基链上双键的位置。通过分析一维和二维核磁共振谱来鉴定糖部分。通过气相色谱-质谱法确定了多不饱和脂肪酸双键的位置，并在某些情况下确定了它们的几何形状。这是甘薯叶中半乳糖脂的首次报道。
• Synthesis of digalactosyl diacylglycerols and their structure–inhibitory activity on human lanosterol synthase
  作者：Rie Tanaka、Yuichi Sakano、Akito Nagatsu、Masaaki Shibuya、Yutaka Ebizuka、Yukihiro Goda

  DOI：10.1016/j.bmcl.2004.10.013

  日期：2005.1

  Digalactosyl and monogalactocyl diacylglycerols (DGDG and MGDG), which were identified as anti-hyperlipemia active components in Colocasia esculenta (Taro), were synthesized. The inhibitory activity of DGDG, MGDG and related compounds on human lanosterol synthase was evaluated as anti-hyperlipemic activity. DGDG with two myristoyl groups at both sn-1 and sn-2 positions and with an oleoyl group at the sn-1 position showed the most potent activity. (C) 2004 Elsevier Ltd. All rights reserved.