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UC223

10-Hydroxywarfarin

Name: 10-Hydroxywarfarin
Brand: SIGMA

Synonym(s):

4-Dihydroxy-3-(2-hydroxy-3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one

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About This Item

Empirical Formula (Hill Notation):

C₁₉H₁₆O₅

CAS Number:

83219-99-2

Molecular Weight:

324.33

NACRES:

NA.77

PubChem Substance ID:

329827661

UNSPSC Code:

12161501

MDL number:

MFCD00272676

Form:

solid

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form

solid

color

colorless

mp

183-185 °C

solubility

DMSO: soluble, methanol: soluble

storage temp.

2-8°C

SMILES string

CC(=O)C(O)C(c1ccccc1)C2=C(O)c3ccccc3OC2=O

InChI

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

InChI key

BPZSPAZBZFZZBN-UHFFFAOYSA-N

Application

10-Hydroxywarfarin has been used for stereo-specific metabolic studies. 10-Hydroxywarfarin has also been used to study its inhibitory effects on CYP2C9.

Biochem/physiol Actions

Major CYP3A4 metabolite of (R)-warfarin.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

10-Hydroxywarfarin is soluble in methanol and DMSO.

pictograms

GHS06,GHS05

signalword

Danger

hcodes

H300,H318

pcodes

P264 - P270 - P280 - P301 + P310 - P305 + P351 + P338 - P405

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Investigation of hepatic warfarin metabolism activity in rodenticide-resistant black rats (Rattus rattus) in Tokyo by in situ liver perfusion.

Kazuki Takeda et al.

Pesticide biochemistry and physiology, 148, 42-49 (2018-06-13)

Anti-blood coagulation rodenticides, such as warfarin, have been used all over the world. They inhibit vitamin K epoxide reductase (VKOR), which is necessary for producing several blood clotting factors. This inhibition by rodenticides results in lethal hemorrhage in rodents. However

Kinetic study of cytochrome P450 3A4 activity on warfarin by capillary electrophoresis with fluorescence detection.

Jie Zhang et al.

Journal of chromatography. A, 1082(2), 235-239 (2005-07-23)

The use of capillary electrophoresis (CE) for the determination of cytochrome P450 3A4 (CYP3A4) activity with R-warfarin as a substrate was investigated. CYP3A4 activity was determined by the quantitation of the product, 10-hydroxywarfarin, based on separation by CE. The separation

Chemical synthesis, absolute configuration, and stereochemistry of formation of 10-hydroxywarfarin: a major oxidative metabolite of (+)-(R)-warfarin from hepatic microsomal preparations.

R F Lawrence et al.

Chirality, 2(2), 96-105 (1990-01-01)

The synthesis of a diastereomerically pure 10-hydroxywarfarin [4-hydroxy-3-(2-hydroxy-3-oxo-1-phenylbutyl)-2H-1 benzopyran-2-one] was accomplished in three steps from racemic warfarin. The relative configuration of the synthetic product was established by conversion to a cyclic derivative followed by NMR and X-ray diffraction analysis. Absolute

Novel revelation of warfarin resistant mechanism in roof rats (Rattus rattus) using pharmacokinetic/pharmacodynamic analysis.

Kazuki Takeda et al.

Pesticide biochemistry and physiology, 134, 1-7 (2016-12-05)

Roof rats (Rattus rattus) live mainly in human habitats. Heavy use of rodenticides, such as warfarin, has led to the development of drug resistance, making pest control difficult. There have been many reports regarding mutations of vitamin K epoxide reductase

Quantitative liquid chromatography/mass spectrometry/mass spectrometry warfarin assay for in vitro cytochrome P450 studies.

Z Y Zhang et al.

Analytical biochemistry, 298(1), 40-49 (2001-10-25)

A sensitive assay using high-performance liquid chromatography tandem mass spectrometry (MS/MS) has been established for the quantitative analysis of cytochrome P450 form-specific activities using warfarin as a probe substrate. Four metabolites, 6-, 7-, 8-, and 10-hydroxywarfarin, were chromatographically resolved within

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Global Trade Item Number

SKU	GTIN
UC223-10MG	04061832932026
UC223-5MG	04061832932033

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