3-Hydroxyacetaminophen - CAS 37519-14-5
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
3-Hydroxyacetaminophen
Catalog Number:
37519-14-5
Synonyms:
Acetaminophen metabolite 3-hydroxy-acetaminophen; N-(3,4-dihydroxyphenyl)acetamide;
CAS Number:
37519-14-5
Description:
A metabolite of acetaminophen, which is is a pain reliever and a fever reducer.
Molecular Weight:
167.16
Molecular Formula:
C8H9NO3
Quantity:
Milligrams-Grams
Quality Standard:
Enterprise Standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC(=O)NC1=CC(=C(C=C1)O)O
InChI:
1S/C8H9NO3/c1-5(10)9-6-2-3-7(11)8(12)4-6/h2-4,11-12H,1H3,(H,9,10)
InChIKey:
IPFBMHOMTSBTSU-UHFFFAOYSA-N
Targets:
Others
Chemical Structure
CAS 37519-14-5 3-Hydroxyacetaminophen

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Reference Reading


1.Role of CYP2A5 and 2G1 in acetaminophen metabolism and toxicity in the olfactory mucosa of the Cyp1a2(-/-) mouse.
Genter MB1, Liang HC, Gu J, Ding X, Negishi M, McKinnon RA, Nebert DW. Biochem Pharmacol. 1998 Jun 1;55(11):1819-26.
Acetaminophen (AP) is a widely-used analgesic agent that has been linked to human liver and kidney disease with prolonged or high-dose usage. In rodents, the target organs that are affected include liver, kidney, and the olfactory mucosa. AP toxicity requires cytochrome P450(CYP)-mediated metabolic activation, and the isozymes CYP1A2, 2E1, and 3A are known to activate AP in the human. In the present study, we determined that olfactory mucosal toxicity of AP was not different between the Cyp1a2(+/+) wild-type and the Cyp1a2(-/-) knockout mouse, whereas the hepatic toxicity of AP was significantly diminished in Cyp1a2(-/-) mice. Western blots of olfactory mucosa revealed that CYP2E1 and CYP3A levels are similar between untreated Cyp1a2(+/+) and Cyp1a2(-/-) mice. Diallyl sulfide (DAS), a known inhibitor of CYP2E1 and of CYP2A10/2A11 (the rabbit orthologue of mouse CYP2A5), completely eliminated olfactory toxicity of AP in both the Cyp1a2(-/-) and wild-type mouse olfactory mucosa.
2.Dysmorphogenesis elicited by microinjected acetaminophen analogs and metabolites in rat embryos cultured in vitro.
Stark KL1, Lee QP, Namkung MJ, Harris C, Juchau MR. J Pharmacol Exp Ther. 1990 Oct;255(1):74-82.
Direct additions of acetaminophen (APAP), 3,5-dimethylacetaminophen, 3-hydroxyacetaminophen or 3-methoxyacetaminophen to the medium of cultured embryos each produced an increased incidence of morphologically similar, abnormally open anterior neuropores. Approximate concentrations required to produce an equal incidence were 0.5 mM, 1.0 mM, 0.1 mM and 0.75 mM, respectively. In contrast, 2.6-dimethylacetaminophen and N-acetyl-p-benzoquinoneimine failed to produce elevated incidences of abnormal neurulation unaccompanied by marked growth retardation. However, with intra-amniotic microinjections, 3-hydroxyacetaminophen and N-acetyl-p-benzoquinoneimine were roughly equipotent for eliciting abnormal neurulation, whereas 3-methoxyacetaminophen required greater than 30-fold higher concentrations. This suggests that N-acetyl-p-benzoquinoneimine does not readily transit the visceral yolk sac and would likely not be a major factor in APAP-elicited neural tube abnormalities unless generated in target tissues.
3.Selective vasodilator and chronotropic actions of 3',4'-dihydroxyflavonol in conscious sheep.
Wang S1, Dusting GJ, Woodman OL, May CN. Eur J Pharmacol. 2004 Apr 26;491(1):43-51.
Flavonoids are known to relax isolated large arteries, but the cardiovascular actions of flavonoids are not well studied in vivo. Hence, we determined the systemic and regional haemodynamic responses to a novel synthetic flavonol, 3',4'-dihydroxyflavonol (DiOHF), in conscious sheep previously instrumented with flow probes on the aorta and coronary, mesenteric, renal, and iliac arteries. Intravenous injection of DiOHF (1.0 mg/kg) caused a delayed but prolonged vasodilatation in the coronary and renal vascular beds, with no changes in the mesenteric or iliac vascular beds. DiOHF induced prolonged increases in heart rate and cardiac output without altering arterial pressure. Pretreatment with Nomega-nitro-L-arginine, a nonspecific inhibitor of nitric oxide synthase, abolished all the cardiovascular effects of DiOHF. The results indicate that DiOHF caused a nitric oxide-dependent vasodilatation of the coronary and renal vasculature and an increase in cardiac output due to its chronotropic action.
4.Enzymatic synthesis of 3'-hydroxyacetaminophen catalyzed by tyrosinase.
Valero E1, Lozano MI, Varón R, García-Carmona F. Biotechnol Prog. 2003 Nov-Dec;19(6):1632-8.
3'-Hydroxyacetaminophen, a catechol metabolite of N-acetyl-p-aminophenol (acetaminophen) and N-acetyl-m-aminophenol (a structural analogue of acetaminophen and considered as a possible alternative because it is not hepatotoxic), is enzymatically synthesized for the first time using mushroom tyrosinase. Although reported to be weakly hepatotoxic in vivo, this catechol derivative of acetaminophen is not commercially available. This compound was obtained from its monophenolic precursor, acetaminophen, using the enzyme tyrosinase in the presence of an excess of ascorbic acid, thus reducing back the o-quinone product of catalytic activity to the catechol acetaminophen derivative. A mathematical model of the system is proposed, which is also applicable to the tyrosinase-mediated synthesis of any o-diphenolic compound from its corresponding monophenol. This synthesis procedure is continuous, easy to perform and control, and adaptable to a bioreactor with the immobilized enzyme for industrial purposes in a nonpolluting way.