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7-Hydroxywarfarin

Name: 7-Hydroxywarfarin
Brand: SIGMA

Synonym(s):

3-(α-Acetonylbenzyl)-4,7-dihydrocoumarin, 4-7-Dihydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one

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About This Item

Empirical Formula (Hill Notation):

C₁₉H₁₆O₅

CAS Number:

17834-03-6

Molecular Weight:

324.33

NACRES:

NA.77

PubChem Substance ID:

329827660

UNSPSC Code:

12161501

MDL number:

MFCD00272668

Form:

solid

Quality level:

200

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Properties

form

solid

Quality Level

200

color

white

mp

220 °C

solubility

DMSO: soluble

storage temp.

2-8°C

SMILES string

CC(CC(C1=C(O)C(C=CC(O)=C2)=C2OC1=O)C3=CC=CC=C3)=O

InChI

1S/C19H16O5/c1-11(20)9-15(12-5-3-2-4-6-12)17-18(22)14-8-7-13(21)10-16(14)24-19(17)23/h2-8,10,15,21-22H,9H2,1H3

InChI key

SKFYEJMLNMTTJA-UHFFFAOYSA-N

Description

Application

7-Hydroxywarfarin can be used for the metabolic assays of (S)-warfarin.

Biochem/physiol Actions

CYP2C9 metabolite of (S)-warfarin.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

7-Hydroxywarfarin is soluble in DMSO.

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This Item	UC283	SML1270	SML2365
Sigma-Aldrich UC211 7-Hydroxywarfarin	Sigma-Aldrich UC283 7-Hydroxycoumarin sulfate potassium salt	Sigma-Aldrich SML1270 YZ9	Sigma-Aldrich SML2365 Phenprocoumon
form solid	form solid	form powder	form powder
Quality Level 200	Quality Level 200	Quality Level 100	Quality Level -
storage temp. 2-8°C	storage temp. −70°C	storage temp. −20°C	storage temp. 2-8°C
solubility DMSO: soluble	solubility H₂O: soluble, methanol: soluble	solubility DMSO: 5 mg/mL, clear (warmed)	solubility DMSO: 2 mg/mL, clear
color white	color white to off-white	color white to beige	color white to beige
mp 220 °C	mp 204-205 °C	mp -	mp -

pictograms

GHS05,GHS07

signalword

Danger

hcodes

H302,H318

pcodes

P280 - P301 + P312 + P330 - P305 + P351 + P338 + P310

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Slow R-warfarin 7-hydroxylation mediated by P450 2C19 genetic variants in cynomolgus monkeys in vivo.

Masahiro Utoh et al.

Biochemical pharmacology, 95(2), 110-114 (2015-03-25)

Cynomolgus monkeys are widely used as non-human primate species in preclinical studies, due to their close evolutionary relationship to humans. Monkey cytochrome P450 2C19 (formerly known as P450 2C75), highly homologous to human P450 2C19, has been identified to be

Highly sensitive and specific high-performance liquid chromatographic analysis of 7-hydroxywarfarin, a marker for human cytochrome P-4502C9 activity.

D Lang et al.

Journal of chromatography. B, Biomedical applications, 672(2), 305-309 (1995-10-20)

The formation of 7-hydroxywarfarin in incubations of (S)-warfarin with human liver microsomes reflects their cytochrome P-4502C9 activity. This paper describes a rapid high-performance liquid chromatographic method for the determination of 7-hydroxywarfarin with high sensitivity, selectivity, and a simple sample clean-up

CYP2C9-catalyzed metabolism of S-warfarin to 7-hydroxywarfarin in vivo and in vitro in chimeric mice with humanized liver.

Tae Inoue et al.

Drug metabolism and disposition: the biological fate of chemicals, 36(12), 2429-2433 (2008-09-12)

Chimeric mice having humanized livers were constructed by transplantation of human hepatocytes. In this study, we investigated whether these mice have a capacity for drug metabolism similar to that of humans by examining hydroxylation of S-warfarin, which is predominantly metabolized

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Global Trade Item Number

SKU	GTIN
UC211-5MG	04061832931982
UC211-10MG	04061832931975

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