4-(sulfooxy)phenylacetic acid | 3671-10-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 4-(sulfooxy)phenylacetic acid
• 英文别名: 2-[4-(Sulfooxy)phenyl]acetic acid；2-(4-sulfooxyphenyl)acetic acid
• CAS: 3671-10-1
• 化学式: C₈H₈O₆S
• 分子量: 232.214
• InChiKey: IIODELUADFSHIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对羟基苯乙酸 在 三氧化硫吡啶 作用下， 以 水 为溶剂， 反应 1.0h， 以33.8%的产率得到4-(sulfooxy)phenylacetic acid
  参考文献：
  名称：

  Phytochemical and Analytical Characterization of Novel Sulfated Coumarins in the Marine Green Macroalga Dasycladus vermicularis (Scopoli) Krasser

  摘要：

  短筒绿藻形成了一个形态多样的海洋大型藻类群体，其中包括两个姐妹目（苔藓目和星状藻目），它们在其他绿藻中具有独特的特征，即能够形成由单个巨大管状细胞组成的大型分化体。细胞损伤后，一系列保护机制已经进化，包括排出参与形成迅速伤口栓的硫酸化代谢物。在这项研究中，我们调查了星状藻（星状藻目）中硫酸化代谢物的组成，结果分离出两种酚酸和四种香豆素，包括两种新结构，经核磁共振光谱（NMR）阐明为5,8'-双-(6(6')，7(7')-四羟基-3-磺氧基-3'-磺氧基香豆素)，一种名为dasycladin A的新香豆素和7-羟基香豆素-3,6-二磺酸，被命名为dasycladin B。此外，开发了一种用于反相C-18柱上色谱定量这些化合物的分析方法，并进行了验证。方法验证证实，新的分析方法具有良好的线性度（R2 ≥ 0.9986）、精密度（日内R.S.D ≤ 3.71%，日间R.S.D ≤ 7.49%）和准确度（回收率范围为104.06%至97.45%）。对来自不同采集地点、水深和季节的多个星状藻样本进行的分析显示，香豆素含量存在差异，范围从0.26%到1.61%。

  DOI：

  10.3390/molecules23112735

文献信息

• Sulfated phenolic acids from Dasycladales siphonous green algae
  作者：Caroline Kurth、Matthew Welling、Georg Pohnert

  DOI：10.1016/j.phytochem.2015.07.010

  日期：2015.9

  Sulfated aromatic acids play a central role as mediators of chemical interactions and physiological processes in marine algae and seagrass. Among others, Dasycladus vermiculans (Scopoli) Krasser 1898 uses a sulfated hydroxylated coumarin derivative as storage metabolite for a protein cross linker that can be activated upon mechanical disruption of the alga. We introduce a comprehensive monitoring technique for sulfated metabolites based on fragmentation patterns in liquid chromatography/mass spectrometry and applied it to Dasycladales. This allowed the identification of two new aromatic sulfate esters 4-(sulfooxy)phenylacetic acid and 4-(sulfooxy)benzoic acid. The two metabolites were synthesized to prove the mass spectrometry-based structure elucidation in co-injections. We show that both metabolites are transformed to the corresponding desulfated phenols by sulfatases of bacteria. In biofouling experiments with Escherichia coli and Vibrio natriegens the desulfated forms were more active than the sulfated ones. Sulfatation might thus represent a measure of detoxification that enables the algae to store inactive forms of metabolites that are activated by settling organisms and then act as defense. (C) 2015 Published by Elsevier Ltd.
• US6313247B1
  申请人：——

  公开号：US6313247B1

  公开（公告）日：2001-11-06
• [EN] IDENTIFICATION OF EARLY NONINVASIVE BIOMARKERS FOR ALCOHOLIC LIVER DISEASE USING URINARY METABOLOMICS AND THE PPARA-NULL MOUSEI<br/>[FR] IDENTIFICATION DE BIOMARQUEURS NON INVASIFS PRÉCOCES DE L'HÉPATITE ALCOOLIQUE À L'AIDE DE LA MÉTABOLOMIQUE URINAIRE ET DE LA SOURIS I PPAR?-NULL
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2013010093A1

  公开（公告）日：2013-01-17

  The invention provides novel biomarkers for alcoholic liver disease.
• Phytochemical and Analytical Characterization of Novel Sulfated Coumarins in the Marine Green Macroalga Dasycladus vermicularis (Scopoli) Krasser
  作者：Anja Hartmann、Markus Ganzera、Ulf Karsten、Alexsander Skhirtladze、Hermann Stuppner

  DOI：10.3390/molecules23112735

  日期：——

  The siphonous green algae form a morphologically diverse group of marine macroalgae which include two sister orders (Bryopsidales and Dasycladales) which share a unique feature among other green algae as they are able to form large, differentiated thalli comprising of a single, giant tubular cell. Upon cell damage a cascade of protective mechanisms have evolved including the extrusion of sulfated metabolites which are involved in the formation of a rapid wound plug. In this study, we investigated the composition of sulfated metabolites in Dasycladus vermicularis (Dasycladales) which resulted in the isolation of two phenolic acids and four coumarins including two novel structures elucidated by nuclear magnetic resonance spectroscopy (NMR) as 5,8′-di-(6(6′),7(7′)-tetrahydroxy-3-sulfoxy-3′-sulfoxycoumarin), a novel coumarin called dasycladin A and 7-hydroxycoumarin-3,6-disulfate, which was named dasycladin B. In addition, an analytical assay for the chromatographic quantification of those compounds was developed and performed on a reversed phase C-18 column. Method validation confirmed that the new assay shows good linearity (R2 ≥ 0.9986), precision (intra-day R.S.D ≤ 3.71%, inter-day R.S.D ≤ 7.49%), and accuracy (recovery rates ranged from 104.06 to 97.45%). The analysis of several samples of Dasycladus vermicularis from different collection sites, water depths and seasons revealed differences in the coumarin contents, ranging between 0.26 to 1.61%.

  短筒绿藻形成了一个形态多样的海洋大型藻类群体，其中包括两个姐妹目（苔藓目和星状藻目），它们在其他绿藻中具有独特的特征，即能够形成由单个巨大管状细胞组成的大型分化体。细胞损伤后，一系列保护机制已经进化，包括排出参与形成迅速伤口栓的硫酸化代谢物。在这项研究中，我们调查了星状藻（星状藻目）中硫酸化代谢物的组成，结果分离出两种酚酸和四种香豆素，包括两种新结构，经核磁共振光谱（NMR）阐明为5,8'-双-(6(6')，7(7')-四羟基-3-磺氧基-3'-磺氧基香豆素)，一种名为dasycladin A的新香豆素和7-羟基香豆素-3,6-二磺酸，被命名为dasycladin B。此外，开发了一种用于反相C-18柱上色谱定量这些化合物的分析方法，并进行了验证。方法验证证实，新的分析方法具有良好的线性度（R2 ≥ 0.9986）、精密度（日内R.S.D ≤ 3.71%，日间R.S.D ≤ 7.49%）和准确度（回收率范围为104.06%至97.45%）。对来自不同采集地点、水深和季节的多个星状藻样本进行的分析显示，香豆素含量存在差异，范围从0.26%到1.61%。