赤式-5,6-十二烷二醇 | 70859-32-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 赤式-5,6-十二烷二醇
• 中文别名: 赤-5,6-十二烷二醇
• 英文名称: eryhtro-5,6-dodecanediol
• 英文别名: erythro-5,6-dodecanediol；(5S,6R)-Dodecane-5,6-diol
• CAS: 70859-32-4
• 化学式: C₁₂H₂₆O₂
• 分子量: 202.337
• InChiKey: COLYTQSCHUMMSR-NWDGAFQWSA-N

物化性质

• 熔点：
  119.0 to 124.0 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 赤式-5,6-十二烷二醇 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Cork Suberin Molecular Structure: Stereochemistry of the C₁₈Epoxy andvic-Diol ω-Hydroxyacids and α,ω-Diacids Analyzed by NMR

  摘要：

  Suberin is the biopolyester that protects the secondary tissues of plants against environmental variability and aggressions. Cork suberin is composed mostly of C-18 omega-hydroxyacids and alpha,omega-diacids, 9,10-substituted with an unsaturation, an epoxide ring, or a vic-diol group. Although determinant for suberin macromolecular structure, the stereochemistry of these monomers is poorly studied, sometimes with contradictory results. An NMR technique was used here to assign the configuration of the 9,10-epoxy and 9,10-diol groups in C-18 suberin acids, comparing the chemical shifts of diagnostic H-1 and C-13 signals with the ones of model compounds, before and after conversion of the vic-diol group into benzylidene acetal derivatives. The relative configuration was proved to be cis in the C-18 9,10-epoxy and threo in the C-18 9,10-diol suberin acids. These monomers were present in suberin probably as racemic mixtures, as shown by polarimetry. The revealed stereochemistry allows the suberin macromolecule to be built as an ordered array of midchain kinked C-18 acids, reinforced by intramolecular hydrogen bonding.

  DOI：

  10.1021/jf400577k

文献信息

• Cytotoxic Glycosylated Fatty Acid Amides from a <i>Stelletta</i> sp. Marine Sponge
  作者：Victoria Peddie、Kentaro Takada、Shujiro Okuda、Yuji Ise、Yasuhiro Morii、Nobuhiro Yamawaki、Tomohiro Takatani、Osamu Arakawa、Shigeru Okada、Shigeki Matsunaga

  DOI：10.1021/acs.jnatprod.5b00795

  日期：2015.11.25

  We have discovered new glycosylated fatty acid amides, stellettosides, from a Stelletta sp. marine sponge. They were detected through LC-MS analysis of the extract combined with the cytotoxicity assay of the prefractionated sample. Their planar structures were determined by analyses of the NMR and tandem FABMS data. Stellettosides A1 and A2 (1 and 2) as well as stellettosides B1–B4 (3–6) were obtained

  我们已经发现了新的糖基化的脂肪酸酰胺，stellettosides，从Stelletta SP。海洋海绵。通过提取物的LC-MS分析和预分离样品的细胞毒性测定相结合，对它们进行了检测。通过分析NMR和串联FABMS数据确定了它们的平面结构。硬脂甙A1和A2（1和2）以及硬脂甙B1-B4（3 – 6）是不可分离的混合物。仔细分析每种混合物的NMR和串联FABMS数据，以及将串联FABMS数据与合成模型化合物的数据进行比较，使我们能够确定混合物中各成分的结构。手性衍生化后，通过LC-MS确定单糖单元的绝对构型。通过异亚丙基衍生物的1 H NMR数据确定脂肪酸链上邻位氧化次甲基的相对构型。（stellettosides B1-B4的混合物3 - 6）显示出适度的细胞毒性活性对HeLa细胞的IC 50 浓度为9μM，而硬脂甙A1和A2（1和2）的混合物在10μM的浓度下没有活性。
• Cork Suberin Molecular Structure: Stereochemistry of the C₁₈Epoxy and<i>vic</i>-Diol ω-Hydroxyacids and α,ω-Diacids Analyzed by NMR
  作者：Sara Santos、Vanessa Cabral、José Graça

  DOI：10.1021/jf400577k

  日期：2013.7.24

  Suberin is the biopolyester that protects the secondary tissues of plants against environmental variability and aggressions. Cork suberin is composed mostly of C-18 omega-hydroxyacids and alpha,omega-diacids, 9,10-substituted with an unsaturation, an epoxide ring, or a vic-diol group. Although determinant for suberin macromolecular structure, the stereochemistry of these monomers is poorly studied, sometimes with contradictory results. An NMR technique was used here to assign the configuration of the 9,10-epoxy and 9,10-diol groups in C-18 suberin acids, comparing the chemical shifts of diagnostic H-1 and C-13 signals with the ones of model compounds, before and after conversion of the vic-diol group into benzylidene acetal derivatives. The relative configuration was proved to be cis in the C-18 9,10-epoxy and threo in the C-18 9,10-diol suberin acids. These monomers were present in suberin probably as racemic mixtures, as shown by polarimetry. The revealed stereochemistry allows the suberin macromolecule to be built as an ordered array of midchain kinked C-18 acids, reinforced by intramolecular hydrogen bonding.