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UC223

Sigma-Aldrich

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
MDL number:
MFCD00272676
UNSPSC Code:
12161501
PubChem Substance ID:
329827661
NACRES:
NA.77

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

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300,H318

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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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