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A4438

Sigma-Aldrich

p-Acetamidophenyl β-D-glucuronide sodium salt

>98% (TLC)

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Synonym(s):
Acetaminophen glucuronide, Paracetamol glucuronide
Linear Formula:
C14H16NO8Na
CAS Number:
Molecular Weight:
349.27
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

>98% (TLC)

form

powder

impurities

<6% water (Karl Fischer)

color

white to off-white

solubility

water: 25 mg/mL, clear, colorless to light yellow

storage temp.

−20°C

SMILES string

[Na+].CC(=O)Nc1ccc(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C([O-])=O)cc1

InChI

1S/C14H17NO8.Na/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21;/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21);/q;+1/p-1/t9-,10-,11+,12-,14+;/m0./s1

InChI key

OINXIJJEOMGKPB-CYRSAHDMSA-M

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1 of 4

This Item
B4532R2886H6029
solubility

water: 25 mg/mL, clear, colorless to light yellow

solubility

-

solubility

water: 0.5 mg/mL, clear to slightly hazy, orange

solubility

-

form

powder

form

powder

form

powder

form

solid

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

color

white to off-white

color

-

color

-

color

white

impurities

<6% water (Karl Fischer)

impurities

-

impurities

-

impurities

5% water (Karl Fischer)

Application

Acetaminophen glucuronide (AA-Gluc) is used as a reference material in procedures that analyse urine and plasma for acetaminophen metabolites to indicate hepatotoxicity.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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T Andrew Clayton et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(34), 14728-14733 (2009-08-12)
We provide a demonstration in humans of the principle of pharmacometabonomics by showing a clear connection between an individual's metabolic phenotype, in the form of a predose urinary metabolite profile, and the metabolic fate of a standard dose of the
Scott A Reisman et al.
Toxicological sciences : an official journal of the Society of Toxicology, 109(1), 31-40 (2009-02-28)
Acetaminophen (AA) is a widely used antipyretic drug that causes hepatotoxicity at high doses. Nuclear factor erythroid 2-related factor 2 (Nrf2) is a transcription factor that mitigates electrophilic stress from AA by inducing genes, such as NAD(P)H:quinone oxidoreductase 1 (Nqo1)
Carol R Gardner et al.
Toxicological sciences : an official journal of the Society of Toxicology, 125(2), 607-612 (2011-11-04)
Fenbendazole is a broad-spectrum anthelmintic drug widely used to prevent or treat nematode infections in laboratory rodent colonies. Potential interactions between fenbendazole and hepatotoxicants such as acetaminophen are unknown, and this was investigated in this study. Mice were fed a
Mayu Kakehi et al.
Toxicological sciences : an official journal of the Society of Toxicology, 147(2), 360-369 (2015-07-17)
There are various interspecies differences in xenobiotic-metabolizing enzymes. It is known that cats show slow glucuronidation of drugs such as acetaminophen and strong side effects due to the UGT1A6 pseudogene. Recently, the UGT1A6 pseudogene was found in the Northern elephant
Andrew Rowland et al.
Drug metabolism and disposition: the biological fate of chemicals, 43(1), 147-153 (2014-11-09)
This study characterized the kinetics, variability, and factors that affect UDP-glucuronic acid (UDP-GlcUA) uptake by human liver microsomes (HLM). Biphasic kinetics were observed for UDP-GlcUA uptake by HLM. Uptake affinities (assessed as Kd) of the high- and low-affinity components differed

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