37519-14-5

Usage

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 
• 81864-29-1 N-(2,2-dimethylbenzo[1,3]dioxol-5-yl)acetamide 
• 71573-24-5 4-amino-1,2-benzenediol diacetate 
• 36383-33-2 4-nitro-1,2-benzenediol diacetate 
• 6315-89-5 3,4-dimethoxyaniline 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

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.

Practical Cleavage of Acetals by Using an Odorless Thiol Immobilized on Silica

A practical, efficient and general method was developed for the deprotection of a variety of aromatic and aliphatic acetals to their corresponding catechol or diol derivatives using thiol immobilized on silica gel. This is an application for the well-known commercial solid-supported thiol (SiliaMetS Thiol). The procedure is mild and amenable to scale-up. It does not require inert atmosphere and clean conversions were observed. This method is applicable to substituted 1,3-benzodioxole and aliphatic acetals with different functionalities. It offers the advantage of a general route with high yield, which can be undertaken at ambient temperature.

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.

Wavelength-dependent photochemistry of acetaminophen in aqueous solutions

The influence of irradiation wavelength and intensity on photochemistry of acetaminophen (APAP) in aqueous solution was investigated by combination of steady-state and laser flash photolysis as well as HPLC and LC-MS. Steady-state irradiation at 254 nm leads to APAP disappearance with the quantum yield 0.0014 and to formation of 1-(2-amino-5-hydroxyphenyl)ethanone (P1) as a main primary photo-Fries product. In opposite the laser excitation at 266 nm leads predominantly to two-photon ionization of APAP with the quantum yield 0.013 (I = 70 mJ/cm2) and to the formation of one main product of phenoxyl radical reactions - N-(3,4-dihydroxyphenyl)acetamide (P5). Steady-state excitation at 282 nm leads to both P1 and P5 products formation indicating competition of photo-Fries and photoionization processes. The wavelength-dependent mechanism of APAP photolysis is proposed and discussed.

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.

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.

Towards the synthesis of aminodibenzo[b,e][1,4]dioxin derivatives via cationic ruthenium complexes

Double nucleophilic aromatic substitution reactions between N-substituted (η6-1,2-dichlorobenzene)RuCp+ salts and substituted 1,2-benzenediols have been carried out under mild conditions to prepare N-substituted (η6-dibenzo[b,e][1,4]dioxin)ruthenium(II) complexes. The dibenzodioxin ligands were subsequently liberated by photolysis, with radiation from a sunlamp or from a medium pressure Hg lamp (300 nm).

Photochemical Oxygenation of Phenols by Pyrimidopteridine N-Oxide. Comparative Studies with Pyridazine and Isoalloxazine N-Oxides

1,3,7,9-Tetrabutylpyrimidopteridine-2,4,6,8(1H,3H,7H,9H)-tetraone 5-oxide 1 transfers its N-oxide oxygen to phenols, i.e., phenol 5, p-cresol 6, L-tyrosine methyl ester 7, and p-hydroxyacetanilide (acetaminophen) 8, under photochemical conditions to give the corresponding dihydric phenols as major products without any accompanying photochemical intramolecular rearrangements of the N-oxide group taking place.This oxygenation is reasonably explained in terms of a photo-induced single electron transfer (SET) followed by oxygen-atom transfer (the SET mechanism) which occurs via the initial formation of a charge-transfer complex between compound 1 and the phenols employed.Comparative experiments with 3,10-dibutylisoalloxazine 5-oxide 3 and 3-methylpyridazine 2-oxide 4 well demonstrate the simplicity and the mechanistic characteristics of the photochemistry of compound 1.