621-37-4 | 3-Hydroxyphenylacetic acid

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$7.00	$5.00
5g	97%	in stock	$13.00	$9.00
25g	97%	in stock	$40.00	$28.00
100g	97%	in stock	$133.00	$93.00
500g	97%	in stock	$583.00	$409.00

Description

• Catalog Number: AB44599
• Chemical Name: 3-Hydroxyphenylacetic acid
• CAS Number: 621-37-4
• Molecular Formula: C8H8O3
• Molecular Weight: 152.1473
• MDL Number: MFCD00004337
• SMILES: OC(=O)Cc1cccc(c1)O
• NSC Number: 14360

Computed Properties

• Complexity: 144
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 2
• XLogP3: 0.9

Upstream Synthesis Route

3-Hydroxyphenylacetic Acid, also known as para-hydroxyphenylacetic acid or 3-HPA, is a versatile chemical compound widely used in chemical synthesis processes due to its unique properties. In the realm of organic chemistry, 3-Hydroxyphenylacetic Acid serves as a crucial building block for the synthesis of various pharmaceuticals, agrochemicals, and fine chemicals. This compound's hydroxyl and carboxylic acid functional groups make it a valuable intermediate in the production of numerous important molecules. It can be used as a precursor in the synthesis of key pharmaceutical compounds, such as antibiotics, antivirals, and anti-inflammatory drugs. Additionally, 3-Hydroxyphenylacetic Acid plays a vital role in the development of agrochemicals, enabling the creation of pesticides and herbicides essential for crop protection.Furthermore, in the field of material science, 3-Hydroxyphenylacetic Acid is utilized for the production of specialty polymers and resins with specific properties tailored to various industrial applications. Its versatile nature and compatibility with a wide range of chemical reactions make it a valuable component in the toolkit of synthetic chemists seeking to design novel compounds with desired characteristics.Overall, 3-Hydroxyphenylacetic Acid's significance in chemical synthesis lies in its ability to act as a versatile building block for creating a diverse array of compounds essential for pharmaceutical, agricultural, and material science industries.

Literature

• Urinary Time- or Dose-Dependent Metabolic Biomarkers of Aristolochic Acid-Induced Nephrotoxicity in Rats.

  Toxicological sciences : an official journal of the Society of Toxicology 20170301

• Resveratrol and EGCG bind directly and distinctively to miR-33a and miR-122 and modulate divergently their levels in hepatic cells.

  Nucleic acids research 20140101

• SPE-NMR metabolite sub-profiling of urine.

  Analytical and bioanalytical chemistry 20121101

• Molecular modeling study on the possible polymers formed during the electropolymerization of 3-hydroxyphenylacetic acid.

  Journal of molecular graphics & modelling 20120401

• Impact of short-term intake of red wine and grape polyphenol extract on the human metabolome.

  Journal of agricultural and food chemistry 20120328

• Soil and cultivar type shape the bacterial community in the potato rhizosphere.

  Microbial ecology 20120201

• Resolving phenylalanine metabolism sheds light on natural synthesis of penicillin G in Penicillium chrysogenum.

  Eukaryotic cell 20120201

• Proteomics shows new faces for the old penicillin producer Penicillium chrysogenum.

  Journal of biomedicine & biotechnology 20120101

• Functional epitope core motif of the Anaplasma marginale major surface protein 1a and its incorporation onto bioelectrodes for antibody detection.

  PloS one 20120101

• Multiple tyrosine metabolites are GPR35 agonists.

  Scientific reports 20120101

• Interactions with the substrate phenolic group are essential for hydroxylation by the oxygenase component of p-hydroxyphenylacetate 3-hydroxylase.

  The Journal of biological chemistry 20111230

• Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids.

  The Journal of organic chemistry 20110819

• pH-dependent studies reveal an efficient hydroxylation mechanism of the oxygenase component of p-hydroxyphenylacetate 3-hydroxylase.

  The Journal of biological chemistry 20110107

• Genome sequencing and comparative transcriptomics of the model entomopathogenic fungi Metarhizium anisopliae and M. acridum.

  PLoS genetics 20110101

• Antioxidative protection of dietary bilberry, chokeberry and Lactobacillus plantarum HEAL19 in mice subjected to intestinal oxidative stress by ischemia-reperfusion.

  BMC complementary and alternative medicine 20110101

• The homogentisate and homoprotocatechuate central pathways are involved in 3- and 4-hydroxyphenylacetate degradation by Burkholderia xenovorans LB400.

  PloS one 20110101

• Comparative genomic reconstruction of transcriptional networks controlling central metabolism in the Shewanella genus.

  BMC genomics 20110101

• Pyomelanin formation in Aspergillus fumigatus requires HmgX and the transcriptional activator HmgR but is dispensable for virulence.

  PloS one 20110101

• Closely related Campylobacter jejuni strains from different sources reveal a generalist rather than a specialist lifestyle.

  BMC genomics 20110101

• Predicting biological functions of compounds based on chemical-chemical interactions.

  PloS one 20110101

• 3-Hydroxyphenylacetic acid induces the Burkholderia cenocepacia phenylacetic acid degradation pathway - toward understanding the contribution of aromatic catabolism to pathogenesis.

  Frontiers in cellular and infection microbiology 20110101

• Profiling of phenols in human fecal water after raspberry supplementation.

  Journal of agricultural and food chemistry 20101013

• The phenolic acids from bacterial degradation of the mangiferin aglycone are quantified in the feces of pigs after oral ingestion of an extract of Cyclopia genistoides (honeybush tea).

  Nutrition research (New York, N.Y.) 20100501

• Urinary excretion of phenolic acids in rats fed cranberry.

  Journal of agricultural and food chemistry 20100414

• Bioavailability of various polyphenols from a diet containing moderate amounts of berries.

  Journal of agricultural and food chemistry 20100414

• Studies on the mechanism of p-hydroxyphenylacetate 3-hydroxylase from Pseudomonas aeruginosa: a system composed of a small flavin reductase and a large flavin-dependent oxygenase.

  Biochemistry 20100119

• Flavanols and anthocyanins in cardiovascular health: a review of current evidence.

  International journal of molecular sciences 20100101

• An exploratory NMR nutri-metabonomic investigation reveals dimethyl sulfone as a dietary biomarker for onion intake.

  The Analyst 20091101

• Dihydroxylated phenolic acids derived from microbial metabolism reduce lipopolysaccharide-stimulated cytokine secretion by human peripheral blood mononuclear cells.

  The British journal of nutrition 20090701

• Yoghurt impacts on the excretion of phenolic acids derived from colonic breakdown of orange juice flavanones in humans.

  Molecular nutrition & food research 20090501

• Bis(3-hydroxy-phenyl-acetato-κO,O')bis-(1H-imidazole-κN)nickel(II).

  Acta crystallographica. Section E, Structure reports online 20090301

• Procyanidin dimers are metabolized by human microbiota with 2-(3,4-dihydroxyphenyl)acetic acid and 5-(3,4-dihydroxyphenyl)-gamma-valerolactone as the major metabolites.

  Journal of agricultural and food chemistry 20090211

• Exploring and dissecting genome-wide gene expression responses of Penicillium chrysogenum to phenylacetic acid consumption and penicillinG production.

  BMC genomics 20090101

• Non mycobacterial virulence genes in the genome of the emerging pathogen Mycobacterium abscessus.

  PloS one 20090101

• Bioavailability of [2-(14)C]quercetin-4'-glucoside in rats.

  Journal of agricultural and food chemistry 20081224

• Phenylacetic acids were detected in the plasma and urine of rats administered with low-dose mulberry leaf extract.

  Nutrition research (New York, N.Y.) 20080801

• Lipophilic (hydroxy)phenylacetates by solvent-free lipase-catalyzed esterification and transesterification in vacuo.

  Journal of agricultural and food chemistry 20080709

• Oxidative transformation of natural and synthetic phenolic mixtures by Trametes versicolor laccase.

  Journal of agricultural and food chemistry 20080227

• Complete genome of Phenylobacterium zucineum--a novel facultative intracellular bacterium isolated from human erythroleukemia cell line K562.

  BMC genomics 20080101

• The missing link: Bordetella petrii is endowed with both the metabolic versatility of environmental bacteria and virulence traits of pathogenic Bordetellae.

  BMC genomics 20080101

• Weakening of salmonella with selected microbial metabolites of berry-derived phenolic compounds and organic acids.

  Journal of agricultural and food chemistry 20070516

• Novel phacB-encoded cytochrome P450 monooxygenase from Aspergillus nidulans with 3-hydroxyphenylacetate 6-hydroxylase and 3,4-dihydroxyphenylacetate 6-hydroxylase activities.

  Eukaryotic cell 20070301

• Discovery of novel aldose reductase inhibitors characterized by an alkoxy-substituted phenylacetic acid core.

  Archiv der Pharmazie 20061001

• The relative contribution of the small and large intestine to the absorption and metabolism of rutin in man.

  Free radical research 20061001

• Inhibition of advanced glycation end product formation on collagen by rutin and its metabolites.

  The Journal of nutritional biochemistry 20060801

• Kinetic mechanisms of the oxygenase from a two-component enzyme, p-hydroxyphenylacetate 3-hydroxylase from Acinetobacter baumannii.

  The Journal of biological chemistry 20060623

• Human fecal water inhibits COX-2 in colonic HT-29 cells: role of phenolic compounds.

  The Journal of nutrition 20051001

• Synthesis of hydroxytyrosol, 2-hydroxyphenylacetic acid, and 3-hydroxyphenylacetic acid by differential conversion of tyrosol isomers using Serratia marcescens strain.

  Journal of agricultural and food chemistry 20050810

• A two-component hydroxylase involved in the assimilation of 3-hydroxyphenyl acetate in Pseudomonas putida.

  The Journal of biological chemistry 20050715

• Ethers of 3-hydroxyphenylacetic acid as selective gamma-hydroxybutyric acid receptor ligands.

  Bioorganic & medicinal chemistry letters 20050701

• Novel gamma-hydroxybutyric acid (GHB) analogs share some, but not all, of the behavioral effects of GHB and GABAB receptor agonists.

  The Journal of pharmacology and experimental therapeutics 20050601

• Trace analysis of oxidized, nitrated, and chlorinated aromatic amino acids by capillary electrophoresis with electroosmotic flow modification allowing large-volume sample stacking.

  Electrophoresis 20050501

• Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds.

  Free radical biology & medicine 20050315

• Transepithelial transport of microbial metabolites of quercetin in intestinal Caco-2 cell monolayers.

  Journal of agricultural and food chemistry 20050209

• The TyrA family of aromatic-pathway dehydrogenases in phylogenetic context.

  BMC biology 20050101

• Supplementation with grape seed polyphenols results in increased urinary excretion of 3-hydroxyphenylpropionic Acid, an important metabolite of proanthocyanidins in humans.

  Journal of agricultural and food chemistry 20040825

• Colonic metabolism of dietary polyphenols: influence of structure on microbial fermentation products.

  Free radical biology & medicine 20040115

• [Allelopathic effect of p- and m-hydroxy-phenylacetic acid on soybean (Glycine max L.) germination].

  Ying yong sheng tai xue bao = The journal of applied ecology 20030501

• Quercetin derivatives are deconjugated and converted to hydroxyphenylacetic acids but not methylated by human fecal flora in vitro.

  Journal of agricultural and food chemistry 20020313

• A novel two-protein component flavoprotein hydroxylase.

  European journal of biochemistry 20011101

• Metabolism of diafenthiuron by microsomal oxidation: procide activation and inactivation as mechanisms contributing to selectivity.

  Pest management science 20011001