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Merck
CN

UC223

10-Hydroxywarfarin

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

Key Documents

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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

SMILES string

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

InChI key

BPZSPAZBZFZZBN-UHFFFAOYSA-N

form

solid

color

colorless

mp

183-185 °C

solubility

DMSO: soluble, methanol: soluble

storage temp.

2-8°C

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

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

hcodes

H300,H318

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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Certificates of Analysis (COA)

Lot/Batch Number
BCBB1850
BCBB1850V
1385506
096K3255
017K3256

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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
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
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
Drew R Jones et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 879(15-16), 1056-1062 (2011-04-08)
Coumadin (R/S-warfarin) is a commonly prescribed anticoagulant for over ∼20 million Americans. Although highly efficacious, positive clinical outcomes during warfarin therapy depend on maintaining a narrow therapeutic range for the drug. This goal is challenging due to large inter-individual variability
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
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