37519-14-5

Basic information

• Product Name: 3-HYDROXYACETAMINOPHEN
• Synonyms: 3-HYDROXYACETAMINOPHEN;N-(3,4-DIHDYROXYPHENYL)ACETAMIDE;4-Acetylaminoresorcinol;N-(2,4-Dihydroxyphenyl)acetamide;4-AcetylaMinopyrocatechol;Acetaminophen metabolite 3-hydroxy-acetaminophen
• CAS NO: 37519-14-5
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• Product Categories: Various Metabolites and Impurities;Metabolites;Metabolite
• Mol File: 37519-14-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 170-172°C
• Boiling Point: 444.7°Cat760mmHg
• Flash Point: 222.8°C
• Appearance: /
• Density: 1.4g/cm³
• Vapor Pressure: 1.6E-08mmHg at 25°C
• Refractive Index: 1.664
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3-HYDROXYACETAMINOPHEN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXYACETAMINOPHEN(37519-14-5)
• EPA Substance Registry System: 3-HYDROXYACETAMINOPHEN(37519-14-5)

Safety Data

• Hazardous Substances Data: 37519-14-5(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Crystalline Solid

Uses

3-Hydroxyacetaminophen is a metabolite of Acetaminophen (A161220), an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1,2,3).

InChI:InChI=1/C8H9NO3/c1-5(10)9-6-2-3-7(11)8(12)4-6/h2-4,11-12H,1H3,(H,9,10)

Upstream product

• 103-90-2 4-acetaminophenol 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 
• 621-42-1 meta-hydroxyacetanilide 
• 103-84-4 Acetanilid 
• 81864-29-1 N-(2,2-dimethylbenzo[1,3]dioxol-5-yl)acetamide 
• 36383-33-2 4-nitro-1,2-benzenediol diacetate 
• 6315-89-5 3,4-dimethoxyaniline 
• 13047-04-6 4-amino-1,2-benzenediol 
• 108-24-7 acetic anhydride 
• 881-70-9 3',4'-dimethoxyacetanilide 
• 74332-02-8 4-N-acetylamino-1,2-benzenediol diacetate 
• 71573-24-5 4-amino-1,2-benzenediol diacetate 

Downstream Products

• 74331-99-0 4-acetamido-o-benzoquinone 

Relevant articles and documents

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Photocatalytic degradation of acetaminophen over Ag, Au and Pt loaded TiO2 using solar light

The sustainability and feasibility of using solar irradiation instead of UV light in photocatalysis is a promising approach for water remediation. In this study, photocatalytic degradation (PCD) of a widely used analgesic and antipyretic drug, acetaminophen (AP), with noble metal loaded TiO2 photocatalysts (Ag/TiO2, Au/TiO2 and Pt/TiO2) was investigated in aqueous suspension using solar light. The deposition of noble metals (Ag, Au and Pt) onto the TiO2 surface enhanced the PCD of AP under different operating conditions including pH, surfactants and drug excipients. However, lower degradation rate constants of AP were obtained under simulated and direct solar light as compared to UV light. The degradation mechanism of AP under UV as well as simulated solar light was found to follow similar, though not identical, reaction pathways leading to hydroxylated intermediates (e.g. 4-acetamidoresorcinol (4-AR), 4-acetamidocatechol (4-AC) and hydroquinone (HQ)) through competitive routes. The PCD of AP followed a pseudo first order kinetics according to Langmiur-Hinshelwood model. Noble metal (Ag, Au and Pt) loaded TiO2 photocatalysts can be used effectively to degrade AP in water under both solar and UV light.

Advanced oxidation chemistry of paracetamol. UV/H(2)O(2)-induced hydroxylation/degradation pathways and (15)N-aided inventory of nitrogenous breakdown products.

The advanced oxidation chemistry of the antipyretic drug paracetamol (1) with the UV/H(2)O(2) system was investigated by an integrated methodology based on (15)N-labeling and GC-MS, HPLC, and 2D (1)H, (13)C, and (15)N NMR analysis. Main degradation pathways derived from three hydroxylation steps, leading to 1,4-hydroquinone/1,4-benzoquinone, 4-acetylaminocatechol and, to a much lesser extent, 4-acetylaminoresorcine. Oxidation of the primary aromatic intermediates, viz. 4-acetylaminocatechol, 1,4-hydroquinone, 1,4-benzoquinone, and 1,2,4-benzenetriol, resulted in a series of nitrogenous and non-nitrogenous degradation products. The former included N-acetylglyoxylamide, acetylaminomalonic acid, acetylaminohydroxymalonic acid, acetylaminomaleic acid, diastereoisomeric 2-acetylamino-3-hydroxybutanedioic acids, 2-acetylaminobutenedioic acid, 3-acetylamino-4-hydroxy-2-pentenedioic acid, and 2,4-dihydroxy-3-acetylamino-2-pentenedioic acid, as well as two muconic and hydroxymuconic acid derivatives. (15)N NMR spectra revealed the accumulation since the early stages of substantial amounts of acetamide and oxalic acid monoamide. These results provide the first insight into the advanced oxidation chemistry of a 4-aminophenol derivative by the UV/H(2)O(2) system, and highlight the investigative potential of integrated GC-MS/NMR methodologies based on (15)N-labeling to track degradation pathways of nitrogenous species.