Home>>Signaling Pathways>> Proteases>> Endogenous Metabolite>>4-Hydroxyphenylacetic acid

4-Hydroxyphenylacetic acid Sale

(Synonyms: 4-羟基苯乙酸) 目录号 : GC33815

A phenolic acid with anti-inflammatory and anti-steatotic activities

4-Hydroxyphenylacetic acid Chemical Structure

Cas No.:156-38-7

规格 价格 库存 购买数量
100mg
¥446.00
现货

电话:400-920-5774 Email: sales@glpbio.cn

Customer Reviews

Based on customer reviews.

Sample solution is provided at 25 µL, 10mM.

产品文档

Quality Control & SDS

View current batch:

产品描述

4-Hydroxyphenylacetic acid is a phenolic acid with anti-inflammatory and anti-steatotic activities.1,2 It is formed via microbial metabolism of aromatic amino acids and polyphenolic compounds, including flavonoid glycosides, by gut microbiota.3,4,5 4-Hydroxyphenylacetic acid (100 mg/kg) inhibits seawater instillation-induced increases in TNF-α, IL-1β, and IL-6 levels in lung tissue and white blood cell numbers in bronchoalveolar lavage fluid (BALF) and prevents lung edema in a rat model of acute lung injury.1 It reverses hepatic steatosis in a mouse model of high-fat diet-induced obesity when administered via a subcutaneous implant at a dose of 350 ?g/day for two weeks.2 Levels of 4-hydroxyphenylacetic acid are increased and decreased in serum and urine, respectively, in rats fed a high-fat diet.3 Serum levels of 4-hydroxyphenylacetic acid are increased in patients with stage III pancreatic cancer.6

1.Liu, Z., Xi, R., Zhang, Z., et al.4-hydroxyphenylacetic acid attenuated inflammation and edema via suppressing HIF-1α in seawater aspiration-induced lung injury in ratsInt. J. Mol. Sci.15(7)12861-12884(2014) 2.Osborn, L.J., Schultz, K., Massey, W., et al.A gut microbial metabolite of dietary polyphenols reverses obesity-driven hepatic steatosisProc. Natl. Acad. Sci. USA119(48)e2202934119(2022) 3.Zeng, Y., Lin, Y., Li, L., et al.Targeted metabolomics for the quantitative measurement of 9 gut microbiota-host co-metabolites in rat serum, urine and feces by liquid chromatography-tandem mass spectrometryJ. Chromatogr. B. Analyt. Technol. Biomed. Life Sci.1110-1111133-143(2019) 4.Kim, D.-H., Jung, E.-A., Sohng, I.-S., et al.Intestinal bacterial metabolism of flavonoids and its relation to some biological activitiesArch. Pharm. Res.21(1)17-23(1998) 5.Chen, H., and Sang, S.Biotransformation of tea polyphenols by gut microbiotaJ. Funct. Foods726-42(2014) 6.Nishiumi, S., Shinohara, M., Ikeda, A., et al.Serum metabolomics as a novel diagnostic approach for pancreatic cancerMetabolomics6(4)518–528(2010)

Chemical Properties

Cas No. 156-38-7 SDF
别名 4-羟基苯乙酸
Canonical SMILES O=C(O)CC1=CC=C(O)C=C1
分子式 C8H8O3 分子量 152.15
溶解度 DMSO : ≥ 100 mg/mL (657.25 mM) 储存条件 Store at -20°C, stored under nitrogen
General tips 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液;一旦配成溶液,请分装保存,避免反复冻融造成的产品失效。
储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
为了提高溶解度,请将管子加热至37℃,然后在超声波浴中震荡一段时间。
Shipping Condition 评估样品解决方案:配备蓝冰进行发货。所有其他可用尺寸:配备RT,或根据请求配备蓝冰。

溶解性数据

制备储备液
1 mg 5 mg 10 mg
1 mM 6.5725 mL 32.8623 mL 65.7246 mL
5 mM 1.3145 mL 6.5725 mL 13.1449 mL
10 mM 0.6572 mL 3.2862 mL 6.5725 mL
  • 摩尔浓度计算器

  • 稀释计算器

  • 分子量计算器

质量
=
浓度
x
体积
x
分子量
 
 
 
*在配置溶液时,请务必参考产品标签上、MSDS / COA(可在Glpbio的产品页面获得)批次特异的分子量使用本工具。

计算

动物体内配方计算器 (澄清溶液)

第一步:请输入基本实验信息(考虑到实验过程中的损耗,建议多配一只动物的药量)
给药剂量 mg/kg 动物平均体重 g 每只动物给药体积 ul 动物数量
第二步:请输入动物体内配方组成(配方适用于不溶于水的药物;不同批次药物配方比例不同,请联系GLPBIO为您提供正确的澄清溶液配方)
% DMSO % % Tween 80 % saline
计算重置

Research Update

Antimicrobial mechanism of 4-Hydroxyphenylacetic acid on Listeria monocytogenes membrane and virulence

Biochem Biophys Res Commun 2021 Oct 1;572:145-150.PMID:34364294DOI:10.1016/j.bbrc.2021.07.096.

4-Hydroxyphenylacetic acid (4-HPCA) is the major intestinal metabolite of kaempferol and polymeric proanthocyanidins whereas the effect of 4-HPCA on Listeria monocytogenes remains unknown. In this study, we investigated the effect and mechanism of action of 4-HPCA on the highly lethal foodborne pathogen Listeria monocytogenes. Our results indicated that 4-HPCA inhibited L. monocytogenes growth and proliferation in a dose-dependent manner. In particular, L. monocytogenes displayed negligible growth or proliferation after 4-HPCA treatment (15.61 mM) for 24 h. The impact of 4-HPCA on cell membrane structure and function was investigated in terms of fluorometric cell membrane integrity, zeta potential and relative electrical conductivity. We observed an approximately 15 % fluorescence reduction in the cell membrane after MIC treatment. The zeta potential of the bacteria shifted significantly from -49.74 to -43.70 mV, -36.65 mV and -37.97 mV after treatment with 4-HPCA at the MIC for 0 h, 3 h and 12 h, respectively. The absolute value of the relative electrical conductivities increased significantly following 3 h, 6 h, 9 h and 15 h of 4-HPCA treatment at the MIC level. The results of scanning electron microscopy (SEM) showed that cells treated with 4-HPCA displayed a wrinkled morphology and irregular shapes. Moreover, 4-HPCA obviously decreased the expression of three virulence genes (hlyA, prfA, and inlA) in L. monocytogenes after 12 h of treatment. All these results verified that 4-HPCA, as an effective antibacterial compound against L. monocytogenes, could cause cell death through cell membrane damage and decrease the expression of three virulence factors.

Biosensor-assisted evolution for high-level production of 4-Hydroxyphenylacetic acid in Escherichia coli

Metab Eng 2022 Mar;70:1-11.PMID:34965469DOI:10.1016/j.ymben.2021.12.008.

4-Hydroxyphenylacetic acid (4HPAA) is an important building block for synthesizing drugs, agrochemicals, and biochemicals, and requires sustainable production to meet increasing demand. Here, we use a 4HPAA biosensor to overcome the difficulty of conventional library screening in identification of preferred mutants. Strains with higher 4HPAA production and tolerance are successfully obtained by atmospheric and room temperature plasma (ARTP) mutagenesis coupled with adaptive laboratory evolution using this biosensor. Genome shuffling integrates preferred properties in the strain GS-2-4, which produces 25.42 g/L 4HPAA. Chromosomal mutations of the strain GS-2-4 are identified by whole genome sequencing. Through comprehensive analysis and experimental validation, important genes, pathways and regulations are revealed. The best gene combination in inverse engineering, acrD-aroG, increases 4HPAA production of strain GS-2-4 by 37% further. These results emphasize precursor supply and stress resistance are keys to efficient 4HPAA biosynthesis. Our work shows the power of biosensor-assisted screening of mutants from libraries. The methods developed here can be easily adapted to construct cell factories for the production of other aromatic chemicals. Our work also provides many valuable target genes to build cell factories for efficient 4HPAA production in the future.

4-Hydroxyphenylacetic acid Prevents Acute APAP-Induced Liver Injury by Increasing Phase II and Antioxidant Enzymes in Mice

Front Pharmacol 2018 Jun 19;9:653.PMID:29973881DOI:10.3389/fphar.2018.00653.

Acetaminophen (APAP) overdose is the principal cause of drug-induced acute liver failure. 4-Hydroxyphenylacetic acid (4-HPA), a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. This study seeks to investigate the ability of 4-HPA to protect against APAP-induced hepatotoxicity, as well as the putative mechanisms involved. Mice were treated with 4-HPA (6, 12, or 25 mg/kg) for 3 days, 1 h after the last administration of 4-HPA, a single dose of APAP was intraperitoneally infused for mice. APAP caused a remarkable increase of oxidative stress markers, peroxynitrite formation, and fewer activated phase II enzymes. 4-HPA increased Nrf2 translocation to the nucleus and enhanced the activity of phase II and antioxidant enzymes, and could thereby ameliorate APAP-induced liver injury. Studies reveal that 4-HPA, as an active area of bioactive dietary constituents, could protect the liver against APAP-induced injury, implying that 4-HPA could be a new promising strategy and natural hepatoprotective drug.

4-Hydroxyphenylacetic acid derivatives of inositol from dandelion (Taraxacum officinale) root characterised using LC-SPE-NMR and LC-MS techniques

Phytochemistry 2014 Feb;98:197-203.PMID:24359632DOI:10.1016/j.phytochem.2013.11.022.

The combination of hyphenated techniques, LC-SPE-NMR and LC-MS, to isolate and identify minor isomeric compounds from an ethyl acetate fraction of Taraxacum officinale root was employed in this study. Two distinct fractions of 4-Hydroxyphenylacetic acid derivatives of inositol were isolated and characterised by spectroscopic methods. The (1)H NMR spectra and MS data revealed two groups of compounds, one of which were derivatives of the di-4-hydroxyphenylacetic acid derivative of the inositol compound tetrahydroxy-5-[2-(4-hydroxyphenyl)acetyl] oxycyclohexyl-2-(4-hydroxyphenyl) acetate, while the other group consisted of similar tri-substituted inositol derivatives. For both fractions the derivatives of inositols vary in the number of 4-Hydroxyphenylacetic acid groups present and their position and geometry on the inositol ring. In total, three di-substituted and three tri-substituted 4-Hydroxyphenylacetic acid inositol derivates were identified for the first time along with a further two previously reported di-substituted inositol derivatives.

Metabolomic signature of exposure and response to citalopram/escitalopram in depressed outpatients

Transl Psychiatry 2019 Jul 4;9(1):173.PMID:31273200DOI:10.1038/s41398-019-0507-5.

Metabolomics provides valuable tools for the study of drug effects, unraveling the mechanism of action and variation in response due to treatment. In this study we used electrochemistry-based targeted metabolomics to gain insights into the mechanisms of action of escitalopram/citalopram focusing on a set of 31 metabolites from neurotransmitter-related pathways. Overall, 290 unipolar patients with major depressive disorder were profiled at baseline, after 4 and 8 weeks of drug treatment. The 17-item Hamilton Depression Rating Scale (HRSD17) scores gauged depressive symptom severity. More significant metabolic changes were found after 8 weeks than 4 weeks post baseline. Within the tryptophan pathway, we noted significant reductions in serotonin (5HT) and increases in indoles that are known to be influenced by human gut microbial cometabolism. 5HT, 5-hydroxyindoleacetate (5HIAA), and the ratio of 5HIAA/5HT showed significant correlations to temporal changes in HRSD17 scores. In the tyrosine pathway, changes were observed in the end products of the catecholamines, 3-methoxy-4-hydroxyphenylethyleneglycol and vinylmandelic acid. Furthermore, two phenolic acids, 4-Hydroxyphenylacetic acid and 4-hydroxybenzoic acid, produced through noncanconical pathways, were increased with drug exposure. In the purine pathway, significant reductions in hypoxanthine and xanthine levels were observed. Examination of metabolite interactions through differential partial correlation networks revealed changes in guanosine-homogentisic acid and methionine-tyrosine interactions associated with HRSD17. Genetic association studies using the ratios of these interacting pairs of metabolites highlighted two genetic loci harboring genes previously linked to depression, neurotransmission, or neurodegeneration. Overall, exposure to escitalopram/citalopram results in shifts in metabolism through noncanonical pathways, which suggest possible roles for the gut microbiome, oxidative stress, and inflammation-related mechanisms.