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

Description

3-Hydroxyacetaminophen, also known as paracetamol or acetaminophen, is a light yellow crystalline solid that serves as a metabolite of the widely used analgesic and antipyretic agent, Acetaminophen (A161220). It is commonly utilized for its pain-relieving and fever-reducing properties, making it a popular choice for treating various ailments such as headaches, muscle aches, and arthritis.

Uses

Used in Pharmaceutical Industry:
3-Hydroxyacetaminophen is used as an analgesic and antipyretic agent for its ability to alleviate pain and reduce fever. It is particularly effective in treating conditions like headache, muscle aches, and arthritis, making it a valuable component in the development of pain relief and fever reduction medications.
Used in Over-the-Counter Medications:
3-Hydroxyacetaminophen is also used as an active ingredient in various over-the-counter (OTC) medications, thanks to its effectiveness in providing relief from mild to moderate pain and fever. Its widespread use in OTC drugs highlights its importance in the self-medication market for common ailments.

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

• 103-84-4 Acetanilid 
• 103-90-2 4-acetaminophenol 
• 621-42-1 meta-hydroxyacetanilide 
• 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 
• 74332-02-8 4-N-acetylamino-1,2-benzenediol diacetate 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 
• 81864-29-1 N-(2,2-dimethylbenzo[1,3]dioxol-5-yl)acetamide 
• 71573-24-5 4-amino-1,2-benzenediol diacetate 
• 881-70-9 3',4'-dimethoxyacetanilide 

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.

Acetamidoquinone and acetamidohydroxy derivatives as inhibitors for both dihydroxyacetamido epoxidase and dehydrogenase

A series of monohydroxy and dihydroxyacetanilides, acetamidoquinones and bromoacetamidoquinones have been synthesised and tested as substrates and/or inhibitors of highly purified dihydroxyacetamido epoxidase (DHAE) and dihydroxy acetamido dehydrogenase (DHADH) from Streptomyces LL-C10337. None was found to act as substrates but many selectively inhibit the enzymes. Kinetic analysis has shown that all the compounds act as reversible competitive inhibitors with respect to the substrates 2,5-dihydroxyacetanilide and 2,3-epoxy-1,4-benzoquinone-5-acetanilide. Monohydroxy acetanilides showed weak inhibition to these enzymes compared to the dihydroxy derivatives while the more powerful inhibitors were the benzoquinoneacetanilide and its 5-bromo equivalent.