thomasidioic acid

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: thomasidioic acid
• 英文别名: thomasidoic acid；7-Hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)-6,8-dimethoxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid
• 化学式: C₂₂H₂₂O₁₀
• 分子量: 446.411
• InChiKey: MQRBOKLXGOXXGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  thomasidioic acid 在 Ankistrodesmus braunii C_202.7a 作用下， 以100%的产率得到3,6-dihydroxy-2,4-dimethoxy-7H-benzocyclohepten-7-one
  参考文献：
  名称：

  Biotransformation of sinapic acid by the green algae Stichococcus bacillaris 155LTAP and Ankistrodesmus braunii C202.7a

  摘要：

  Sinapic acid was bioconverted by the green alga Stichococcus bacillaris into 4-hydroxy-3,5-dimethoxybenzoic acid, 4-hydroxy-3,5-dimethoxybenzaldehyde and 4-hydroxy-3,5-dimethoxybenzylic alcohol. Incubation of sinapic acid in a culture of the alga Ankistrodesmus braunii gave 3,6-dihydroxy-2,4-dimethoxy-7H-benzocyclohepten-7-one, a new compound formed by bioconversion of thomasidioic acid, the primary oxidative product of sinapic acid. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00458-1
• 作为产物：
  描述：

  3,5-二甲氧基-4-羟基肉桂酸 在 三氯化铁 作用下， 以 甲醇 为溶剂， 生成 thomasidioic acid
  参考文献：
  名称：

  高压灭菌过程中芥子酸和芥子碱硫酸氢盐的结构变化与有色物质的发展有关

  摘要：

  AbstractStructural changes in sinapic acid during autoclaving were studied using spectral analysis, thin‐layer chromatography, high‐performance liquid chromatography, nuclear magnetic resonance (NMR), and mass spectroscopy. Color properties of sinapic acid and its derivatives were studied by determining the transmittance spectrum, calculating the Commission Internationale de l’Eclairage 1931 tristimulus values and converting to Hunter L a b values. It was found that the colorless sinapic acid aqueous solution (100 µg/mL) turned yellow after 15 min in an autoclave at 121°C and 0.1 MPa. Filtering the yellow aqueous solution through a 0.45‐µm filter removed a brown solid consisting of at least three undetermined colored substances and left a yellow liquid. A newly developed yellow substance, syringaldehyde, was identified in the liquid phase by comparing the NMR and mass spectra of the unknown with those of authentic syringaldehyde. Thomasidioic acid was also found in the liquid phase. Under the same autoclaving conditions, sinapine bisulfate showed no evidence of any structural or color changes.

  DOI：

  10.1007/s11746-999-0021-7

文献信息

• Conversion of phenolics to lignans: Sinapic acid to thomasidioic acid
  作者：M. I. Rubino、S. D. Arntfield、J. L. Charlton

  DOI：10.1007/bf02577839

  日期：1995.12

  Changes in sinapic acid when exposed to aqueous alkaline conditions were elucidated. Sinapic acid was exposed to a volatile buffer (pH 8.5) for 24 h, lyophilized, acidified, extracted, and characterized using nuclear magnetic resonance and mass spectroscopy. The product obtained was identified as the lignan thomasidioic acid. This identification was confirmed by comparison with a synthesized authentic sample of thomasidioic acid. Conversion of sinapic acid to thomasidioic acid under alkaline conditions previously has not been reported. Thomasidioic acid was present after exposure of sinapic acid to pH 8.5 for as few as 6 h. Thomasidioic acid also was formed at pH 7.

  摘要 阐明了山奈酸在水碱性条件下的变化。将山奈酸置于挥发性缓冲液（pH 8.5）中 24 小时，然后冻干、酸化、提取，并利用核磁共振和质谱进行表征。得到的产物被鉴定为木质素 thomasidioic acid。这一鉴定结果通过与合成的真品thomasidioic acid 样品进行比较得到了证实。在碱性条件下将山奈酸转化成托马杉二酸的研究以前从未报道过。山奈酸在 pH 值为 8.5 的环境中暴露 6 小时就会产生托马刁酸，在 pH 值为 7 时也会产生托马刁酸。
• Biotransformation of sinapic acid by the green algae Stichococcus bacillaris 155LTAP and Ankistrodesmus braunii C202.7a
  作者：Marina DellaGreca、Gabriele Pinto、Antonino Pollio、Lucio Previtera、Fabio Temussi

  DOI：10.1016/s0040-4039(03)00458-1

  日期：2003.3

  Sinapic acid was bioconverted by the green alga Stichococcus bacillaris into 4-hydroxy-3,5-dimethoxybenzoic acid, 4-hydroxy-3,5-dimethoxybenzaldehyde and 4-hydroxy-3,5-dimethoxybenzylic alcohol. Incubation of sinapic acid in a culture of the alga Ankistrodesmus braunii gave 3,6-dihydroxy-2,4-dimethoxy-7H-benzocyclohepten-7-one, a new compound formed by bioconversion of thomasidioic acid, the primary oxidative product of sinapic acid. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Structural changes of sinapic acid and sinapine bisulfate during autoclaving with respect to the development of colored substances
  作者：R. Cai、S. D. Arntfield、J. L. Charlton

  DOI：10.1007/s11746-999-0021-7

  日期：1999.4

  AbstractStructural changes in sinapic acid during autoclaving were studied using spectral analysis, thin‐layer chromatography, high‐performance liquid chromatography, nuclear magnetic resonance (NMR), and mass spectroscopy. Color properties of sinapic acid and its derivatives were studied by determining the transmittance spectrum, calculating the Commission Internationale de l’Eclairage 1931 tristimulus values and converting to Hunter L a b values. It was found that the colorless sinapic acid aqueous solution (100 µg/mL) turned yellow after 15 min in an autoclave at 121°C and 0.1 MPa. Filtering the yellow aqueous solution through a 0.45‐µm filter removed a brown solid consisting of at least three undetermined colored substances and left a yellow liquid. A newly developed yellow substance, syringaldehyde, was identified in the liquid phase by comparing the NMR and mass spectra of the unknown with those of authentic syringaldehyde. Thomasidioic acid was also found in the liquid phase. Under the same autoclaving conditions, sinapine bisulfate showed no evidence of any structural or color changes.