(+/-)-threo-guaiacylglycerol-β-O-4'-coniferyl ether | 168393-18-8

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (+/-)-threo-guaiacylglycerol-β-O-4'-coniferyl ether
• 英文别名: erythro-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphe-noxy}-1,3-propanediol；(1S,2S)-1-(3-Methoxy-4-hydroxyphenyl)-2-[2-methoxy-4-[(E)-3-hydroxy-1-propenyl]phenoxy]-1,3-propanediol；(1S,2S)-1-(4-hydroxy-3-methoxyphenyl)-2-[4-[(E)-3-hydroxyprop-1-enyl]-2-methoxyphenoxy]propane-1,3-diol
• CAS: 168393-18-8
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: FYEZJIXULOZDRT-LOKQZNEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Benzoic acid 4-{3-hydroxy-2-[2-methoxy-4-((E)-propenyl)-phenoxy]-propionyl}-2-methoxy-phenyl ester 在 sodium hydroxide 、 sodium tetrahydroborate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 反应 18.0h， 生成 (+/-)-threo-guaiacylglycerol-β-O-4'-coniferyl ether
  参考文献：
  名称：

  Revised structure for a neolignan from Brucea javanica

  摘要：

  On the basis of H-1 and C-13 NMR spectral comparison with natural and synthetic compounds, the neolignan isomers isolated from Brucea javanica for which unusual 8-O-6'-structures were proposed have been reassigned to the conventional 8-O-6'-structures (erythro and threo-guaiacylglycerol-beta-coniferyl ether), respectively. Thus far, there is no evidence for the existence of 8-O-6'-neolignans in nature. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00449-x

文献信息

• Structures of New Aromatics Glycosides from a Japanese Folk Medicine, the Roots of Angelica furcijuga
  作者：Toshio Morikawa、Hisashi Matsuda、Norihisa Nishida、Teruki Ohgushi、Masayuki Yoshikawa

  DOI：10.1248/cpb.52.1387

  日期：——

  Three new aromatics glycosides, hyuganosides II, IIIa, and IIIb, were isolated from a Japanese folk medicine, the roots of Angelica furcijuga KITAGAWA. The structures of the new glycosides were determined on the basis of chemical and physicochemical evidence.

  从一种日本民间药材--毛当归的根中分离出了三种新的芳香族苷--hyuganosides II、IIIa 和 IIIbITAGAWA。根据化学和物理化学证据确定了新苷的结构。
• Glycosides from the Root of <i>Iodes</i> <i>cirrhosa</i>
  作者：Maoluo Gan、Yanling Zhang、Sheng Lin、Mingtao Liu、Weixia Song、Jiachen Zi、Yongchun Yang、Xiaona Fan、Jiangong Shi、Jinfeng Hu、Jiandong Sun、Naihong Chen

  DOI：10.1021/np7007329

  日期：2008.4.1

  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.