(16S)-dihydrosteviol | 110547-87-0

• 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: (16S)-dihydrosteviol
• 英文别名: (16S)-13-hydroxy-ent-kauran-19-oic acid；dihydrosteviol B；(10S)-13-hydroxy-16βH-kauran-19-oic acid；(10S)-13-Hydroxy-16βH-kauran-19-saeure；Dihydrosteviol-B
• CAS: 110547-87-0
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: FFDZEKYNUVRVOG-IVJAHPGJSA-N

物化性质

• 沸点：
  457.2±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (16S)-dihydrosteviol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (4aR)-2t-Hydroxy-4bt,8c,12t-trimethyl-8t-hydroxymethyl-(4arH.8acH)-1,2,4,4a,4b,5,6,7,8,8a,9,10-dodecahydro-3H-2c,10ac-ethano-phenanthren
  参考文献：
  名称：

  The Absolute Configuration of Steviol and Isosteviol

  摘要：

  DOI：

  10.1021/ja00898a025
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 (16S)-dihydrosteviol
  参考文献：
  名称：

  THE STRUCTURE AND STEREOCHEMISTRY OF STEVIOL AND ISOSTEVIOL

  摘要：

  DOI：

  10.1021/ja01486a054

文献信息

• Synthesis and Sensory Evaluation of ent-Kaurane Diterpene Glycosides
  作者：Indra Prakash、Mary Campbell、Rafael Ignacio San Miguel、Venkata Sai Prakash Chaturvedula

  DOI：10.3390/molecules17088908

  日期：——

  rubusoside, stevioside, and rebaudioside-A has been carried out using Pd(OH)₂ and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR spectral data and chemical studies. Also, we report herewith the sensory evaluation of all the

  已使用 Pd(OH) 2 对从甜叶菊中分离出的三种对映贝壳杉烷二萜糖苷，即红花心甙、甜菊甙和莱鲍迪甙-A 进行催化氢化，并已分离出它们相应的二氢衍生物作为产物。还原型甜菊糖苷的合成使用简单的化学方法进行，其结构基于 1D 和 2D NMR 光谱数据和化学研究进行表征。此外，我们在此报告了所有还原化合物相对于它们相应的原始甜菊糖苷和蔗糖对这些分子的甜味特性的感官评价。
• STEVIOSIDE. II. THE STRUCTURE OF THE AGLUCON
  作者：ERICH MOSETTIG、WILLIAM R. NES

  DOI：10.1021/jo01125a013

  日期：1955.7
• New synthesis of diterpenoid (16S)-dihydrosteviol
  作者：R. N. Khaibullin、I. Yu. Strobykina、V. E. Kataev、O. A. Lodochnikova、A. T. Gubaidullin、R. Z. Musin

  DOI：10.1134/s107036320905017x

  日期：2009.5

  A new procedure has been developed for the synthesis of diterpenoid (16S)-dihydrosteviol [(16S)-13-hydroxy-ent-kauran-19-oic acid] by acid hydrolysis (0.7% hydrochloric acid) of SWETA food sweetener and subsequent reduction of the resulting mixture of caurenoids with hydrazine hydrate over Raney nickel. The molecular geometry of (16S)-dihydrosteviol, as well as of Delta(15)-steviol (13-hydroxy-ent-kaur-15-en-19-oic acid), was determined for the first time by X-ray analysis.