(7S,8S)-guaiacyl glycerol | 7095-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (7S,8S)-guaiacyl glycerol
• 英文别名: 1-(4-hydroxy-3-methoxyphenyl)-1,2,3,-propanetriol；(1S,2S)-1-(4-hydroxy-3-methoxyphenyl)propane-1,2,3-triol
• CAS: 7095-33-2
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: LSKFUSLVUZISST-WPRPVWTQSA-N

物化性质

• 沸点：
  483.7±45.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S)-(-)-莰烷酰氯 、 (7S,8S)-guaiacyl glycerol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 1.0h， 生成 4-((1S,2S)-1,2-dihydroxy-3-(((1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carbonyl)oxy)propyl)-2-methoxyphenyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  一种通过 1H NMR 光谱测定含有芳基甘油片段的化合物的相对和绝对构型的巧妙方法

  摘要：

  建立了一种简明的方法来确定芳基甘油的相对和绝对构型，该构型取决于非对映亚甲基质子（H-3）的化学位移差异（ Δδ ），通过1 H NMR 光谱。当使用 DMSO- d 6作为首选溶剂时，苏型构型对应于较大的 Δ δ H3a–H3b值 (>0.15 ppm)，而赤型构型 (<0.07 ppm) 对应于较小的值。此外，借助莰酰氯的简单酰化反应确定了绝对构型。在苏式对映体中， 1R , 2R构型的Δδ值为<0.15ppm， 1S , 2S构型的Δδ值为>0.20ppm。赤型对映体中，1 R ,2 S的Δδ值为>0.09 ppm，1 S ,2 R的Δδ值为<0.05 ppm。值得注意的是，这个经验规则在CDCl 3中是无效的。此外，该方法还通过量子1 H NMR计算得到验证。

  DOI：

  10.1039/d0ra09712h
• 作为产物：
  描述：

  (+)-(7S,8S)-guaiacylglycerol 8-O-β-D-glucopyranoside 在 β-glucosidase 作用下， 以 水 为溶剂， 以4.5 mg的产率得到(7S,8S)-guaiacyl glycerol
  参考文献：
  名称：

  Glycosides from the Root of Iodes cirrhosa

  摘要：

  Seven new neolignan glycosides (1-7), two arylglycerol glycosides (8, 9), and 18 known glycosides have been isolated from an ethanolic extract of the root of lodes cirrhosa. Their structures including absolute configurations were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo and erythro 8-4'-oxyneolignans and arylglycerols in different solvents, the validity of J(7,8) and Delta delta(C8-C7) values to distinguish threo and erythro derivatives was discussed. In the in vitro assays, compound 4 and liriodendrin (17) both showed activity against glutamate-induced PC12 cell damage at 10(-5) M.

  DOI：

  10.1021/np7007329

文献信息

• Phenolic glucoside gallates from quercus mongolica and q. acutissima
  作者：Kanji Ishimaru、Gen-Ichiro Nonaka、Itsuo Nishioka

  DOI：10.1016/s0031-9422(00)82367-5

  日期：1987.1
• Adler,E.; Gustafsson,B., Acta Chemica Scandinavica (1947), 1963, vol. 17, p. 27 - 36
  作者：Adler,E.、Gustafsson,B.

  DOI：——

  日期：——
• Enantioselective Synthesis of Phenylpropanetriols
  作者：Marina DellaGreca、Antonio Fiorentin、Pietro Monaco、Lucio Previtera

  DOI：10.1080/00397919808004916

  日期：1998.10

  The four stereomer 1-(4-hydroxy-3-methoxy)-phenyl-1,2,3-propanetriols were obtained in about 30% yields starting from ferulic acid by a synthesis based on osmium catalyzed asymmetric dihydroxylation.
• Structural characterization of phenolic constituents from the rhizome of Imperata cylindrica var. major and their anti-inflammatory activity
  作者：Jing-Ya Ruan、Hui-Na Cao、Hong-Yu Jiang、Hui-Min Li、Mi-Mi Hao、Wei Zhao、Ying Zhang、Yu Han、Yi Zhang、Tao Wang

  DOI：10.1016/j.phytochem.2021.113076

  日期：2022.4
• Anti-inflammatory terpenes from Schefflera rubriflora C. J. Tseng &amp; G. Hoo with their TNF-α and IL-6 inhibitory activities
  作者：Fenghua Li、Jian Zhang、Mingbao Lin、Xianming Su、Changkang Li、Hongqing Wang、Baoming Li、Ruoyun Chen、Jie Kang

  DOI：10.1016/j.phytochem.2019.03.021

  日期：2019.7

  The 95% ethanol extract and its EtOAc and n-BuOH fractions obtained from the leaves and twigs of Schefflera rubriflora C. J. Tseng & G. Hoo showed significant inhibitory activities (33.6%, 35.7% and 40.6%, respectively) against croton oil-induced ear inflammation in mice. Bioactivity-guided isolation and separation gave eight previously undescribed terpenes or terpene glycosides. Structural elucidation was based on UV, IR, and NMR spectroscopy, MS, experimental and calculated ECD data, and Mosher's method. To identify anti-inflammatory components from the extract, all the compounds were evaluated for tumor necrosis factor-alpha (TNF-alpha) and interleukine-6 (IL-6) inhibitory activities. Four undescribed compounds inhibited mRNA expression of TNF-alpha and IL-6 with IC50 values of 15.3-52.4 mu M.