3-Hydroxyacetaminophen

• CAS: 37519-14-5
• Catalog Number: ACM37519145
• Category: Main Products
• Molecular Weight: 167.16
• Molecular Formula: C8H9NO3
• Synonyms: N-(3,4-dihydroxyphenyl)acetamide
• IUPAC Name: N-(3,4-dihydroxyphenyl)acetamide
• SMILES: CC(=O)NC1=CC(=C(C=C1)O)O
• InChI Key: IPFBMHOMTSBTSU-UHFFFAOYSA-N
• Boiling Point: 444.7ºC at 760 mmHg
• Melting Point: 170-172ºC
• Flash Point: 222.8ºC
• Density: 1.4g/cm³
• Exact Mass: 167.05800

Case Study

The study on the transformation of 3-hydroxyacetaminophen as a pharmaceutical product

Li, Juying, Qingfu Ye, and Jay Gan.Water research 49 (2014): 44-52.

Acetaminophen is one of the most widely used drugs in humans. Trace amounts of acetaminophen are frequently detected in treated wastewater and affected surface or groundwater resources. This study combined C4 labeling and LC-MS/MS techniques to evaluate the dissipation and transformation pathways of acetaminophen under various conditions. During 120-day aerobic incubation, the mineralization rate of C4-acetaminophen reached 17.0-0.8%, but mineralization was significantly inhibited after biosolid sterilization or repair. Immediately after treatment, most C4 residues became unextractable or unbound, at a level representing 73.4-93.3% of the applied amount at the end of the latency period. Eight intermediates were identified, including 3-hydroxyacetaminophen and hydroquinone.
Selected soil extracts were further analyzed by LC-MS/MS to identify intermediates after sample reduction. The identities of the degradation intermediates were confirmed by matching retention times, observed molecular ions, precursor ion spectra, and fragmentation patterns with relevant commercial standards. All eight carbon-containing metabolites were identified in the order of increasing retention time under chromatographic conditions: 3-hydroxyacetaminophen (M1), hydroquinone (M2), 1,4-benzoquinone (M3), N-acetyl-p-benzoquinone ketone (NAPQI) (M4), acetyl-p-benzoquinone (M5), 4-methoxybenzene (M6), 2-hexosilicate (M7), and 1,4-dimethoxybenzene (M8).

3-Hydroxyacetaminophen's role in cross-linking enzyme aggregate research

Ba, Sidy, et al. Science of the total environment 487 (2014): 748-755.

Lactase and tyrosinase are ubiquitous enzymes in nature, originating from bacteria, fungi, plants, etc. Lactase and tyrosinase were investigated as a cross-linking enzyme aggregate (combi-CLEA). Combi-CLEA exhibits specific activities of 12.3 U/g for lactase and 167.4 U/g for tyrosinase, demonstrating high enzyme activity at pH 5-8 and temperatures of 5-30°C, significant resistance to denaturation, and no diffusion restriction on the active site according to Michaelis-Menten kinetic parameters. In batch mode, combi-CLEA converted over 80% of acetaminophen in municipal wastewater to nearly 100%, and over 90% in hospital wastewater. UPLC-MS analysis of acetaminophen metabolites showed that its oligomers formed dimers, trimers, tetramers, and 3-hydroxyacetaminophen.
When lactase and tyrosinase are mixed with acetaminophen, it was initially found that the acetaminophen dimer and its metabolite 3-hydroxyacetaminophen exist separately in the oxidation reactions of the drug with lactase and tyrosinase, respectively. However, as the reaction proceeds, 3-hydroxyacetaminophen disappears from the reaction products, unlike the acetaminophen dimer. Further transformation is possible due to the residual activity of any one (or both) enzymes or their metabolites. Further analytical studies are needed to elucidate the numerous and more complex possible pathways that produce metabolites from these transformations.

3-Hydroxyacetaminophen involved in cross-linking enzyme aggregate studies

Villota, N., et al. Science of the Total Environment 649 (2019): 1434-1442.

Acetaminophen aqueous solution, after ozone treatment, exhibits a strong red color, the intensity of which depends on the ozone dosage and the initial pH of the solution. Subsequently, the red color gradually weakens and turns yellow. The color reaction is most active at an initial pH of 12.0 and an ozone flow rate of 4.2 mg/min. A mechanism describing the color reaction was investigated, the main pathway of which is the initial hydroxylation of acetaminophen to 3-hydroxyacetaminophen, followed by the formation of 2-amino-5-hydroxyacetylbenzophenone. These compounds then degrade into colored oxidation byproducts. A model describing the evolution of the color reaction process was also proposed, assuming that both color development and degradation follow first-order kinetics.
For each ozone treatment experiment, a 1.0 L solution of acetaminophen was prepared and added to a semi-continuously operating jacketed reactor. The experiment was conducted at a temperature of 25.0 °C maintained by a constant-temperature water bath. An ozone/oxygen mixture was generated by an ozone generator and injected into the bottom of the reactor through a metal diffuser. The reaction medium was stirred to ensure homogeneity. During the reaction, acetaminophen was hydroxylated to generate 3-hydroxyacetaminophen, and the results were analyzed using instruments.

3-Hydroxyacetaminophen used in a study on the decrease in acetaminophen potency in bananas

Uesawa, Yoshihiro, and Naotaka Tsuji. Plos one 13.10 (2018): e0205612.

Edible banana portions contain high levels of polyphenol oxidase, which catalyzes reactions in the melanin formation pathway. Tyrosine is a physiological substrate of polyphenol oxidase and its structure is similar to that of acetaminophen. The study investigated whether banana extract caused structural changes in acetaminophen and a decrease in its potency. Acetaminophen concentrations in banana extract were measured under different conditions to characterize incompatibility. Reaction products, including 3-hydroxyacetaminophen, in solution were identified by liquid chromatography/electrospray ionization/mass spectrometry. In the presence of banana extract, the potency of acetaminophen decreased over time. A novel interaction between banana and acetaminophen was investigated and characterized. Future studies on this interaction in humans are expected to establish a safe and effective acetaminophen antipyretic and analgesic regimen.
Acetaminophen was incubated in a 50% banana supernatant sample. After incubation, 10 volumes of ice-cold acetonitrile were added to the reaction mixture. The sample was vigorously mixed for 20 seconds and centrifuged at 16,000 g for 5 minutes at 4°C; the supernatant (5 μL) was then injected into LC/EM/MS/MS curing buffer. ESI mass spectra were obtained using an LCMS system and an ESI probe equipped with a reversed-phase analysis cap. The negative ion 3-hydroxyacetaminophen and the positive ion in the reaction mixture co-incubated with banana supernatant and acetaminophen were also monitored in negative and positive ion modes, respectively, in scan mode.

Custom Q&A

What is the molecular formula of 3-Hydroxyacetaminophen?

The molecular formula of 3-Hydroxyacetaminophen is C8H9NO3.

What are the synonyms for 3-Hydroxyacetaminophen?

The synonyms for 3-Hydroxyacetaminophen are N-(3,4-Dihydroxyphenyl)acetamide, Acetamide, N-(3,4-dihydroxyphenyl)-, and Acetaminophen metabolite 3-hydroxy-acetaminophen.

What is the molecular weight of 3-Hydroxyacetaminophen?

The molecular weight of 3-Hydroxyacetaminophen is 167.16 g/mol.

When was 3-Hydroxyacetaminophen created?

3-Hydroxyacetaminophen was created on March 26, 2005.

When was 3-Hydroxyacetaminophen last modified?

The last modification of 3-Hydroxyacetaminophen occurred on October 21, 2023.

What is the IUPAC name of 3-Hydroxyacetaminophen?

The IUPAC name of 3-Hydroxyacetaminophen is N-(3,4-dihydroxyphenyl)acetamide.

What is the InChI of 3-Hydroxyacetaminophen?

The InChI of 3-Hydroxyacetaminophen is InChI=1S/C8H9NO3/c1-5(10)9-6-2-3-7(11)8(12)4-6/h2-4,11-12H,1H3,(H,9,10).

What is the InChIKey of 3-Hydroxyacetaminophen?

The InChIKey of 3-Hydroxyacetaminophen is IPFBMHOMTSBTSU-UHFFFAOYSA-N.

What is the CAS number of 3-Hydroxyacetaminophen?

The CAS number of 3-Hydroxyacetaminophen is 37519-14-5.

What is the XLogP3 value of 3-Hydroxyacetaminophen?

The XLogP3 value of 3-Hydroxyacetaminophen is 1.2.