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A7205

Sigma-Aldrich

3-Acetamidophenol

97%

Synonym(s):

3′-Hydroxyacetanilide

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About This Item

Linear Formula:
CH3CONHC6H4OH
CAS Number:
621-42-1
Molecular Weight:
151.16
Beilstein:
907998
EC Number:
210-687-0
MDL number:
MFCD00002263
UNSPSC Code:
12352100
PubChem Substance ID:
24891188
NACRES:
NA.22

Assay

97%

form

crystals

mp

145-148 °C (lit.)

SMILES string

CC(=O)Nc1cccc(O)c1

InChI

1S/C8H9NO2/c1-6(10)9-7-3-2-4-8(11)5-7/h2-5,11H,1H3,(H,9,10)

InChI key

QLNWXBAGRTUKKI-UHFFFAOYSA-N

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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A J Streeter et al.
Drug metabolism and disposition: the biological fate of chemicals, 12(5), 565-576 (1984-09-01)
Incubations of 3'-hydroxyacetanilide (3HAA) with hepatic microsomal preparations from phenobarbital-pretreated mice led to the formation of three products of aromatic hydroxylation, viz. 2',5'-, 3',4'-, and 2',3'-dihydroxyacetanilide, which were identified by GC/MS techniques and quantified by GLC analysis. NADPH-dependent covalent binding
M S Rashed et al.
Chemical research in toxicology, 2(1), 41-45 (1989-01-01)
3'-Hydroxyacetanilide (AMAP) is a nonhepatotoxic regioisomer of acetaminophen (APAP) that nonetheless does form reactive metabolites which bind to hepatic proteins. Because differences in the nature of reactive metabolites formed from AMAP and APAP may explain differences in their propensity to
T G Myers et al.
Chemical research in toxicology, 8(3), 403-413 (1995-04-01)
Acetaminophen (4'-hydroxyacetanilide), a widely used analgesic/antipyretic drug, is hepatotoxic in large doses, whereas the m-hydroxy isomer of acetaminophen, 3'-hydroxyacetanilide, is not hepatotoxic. Both are oxidized by mouse liver cytochromes P-450 to reactive metabolites that bind covalently to hepatic proteins. Because
Metabolic alterations resulting from the inhibition of mitochondrial respiration by acetaminophen in vivo.
R L Esterline et al.
Biochemical pharmacology, 38(14), 2390-2392 (1989-07-15)
Robert H Pierce et al.
Biochemical pharmacology, 64(3), 413-424 (2002-07-31)
Overdose of the popular, and relatively safe, analgesic acetaminophen (N-acetyl-p-aminophenol, APAP, paracetamol) can produce a fatal centrilobular liver injury. APAP-induced cell death was investigated in a differentiated, transforming growth factor alpha (TGFalpha)-overexpressing, hepatocyte cell line and found to occur at
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