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UC208

Sigma-Aldrich

6-Hydroxywarfarin

Synonym(s):

3-(α-Acetonylbenzyl)-4,6-dihydrocoumarin, 4-6-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:
17834-02-5
Molecular Weight:
324.33
MDL number:
MFCD00272665
UNSPSC Code:
12161501
PubChem Substance ID:
329827657

color

white

mp

119-120 °C

solubility

DMSO: soluble

storage temp.

2-8°C

SMILES string

CC(=O)CC(c1ccccc1)C2=C(O)c3cc(O)ccc3OC2=O

InChI

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

InChI key

IQWPEJBUOJQPDE-UHFFFAOYSA-N

Biochem/physiol Actions

CYP1A2/2C9 metabolite of (R)-warfarin

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

6-Hydroxywarfarin is soluble in DMSO.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A E Rettie et al.
Chemical research in toxicology, 5(1), 54-59 (1992-01-01)
Previous kinetic studies have identified a high-affinity (S)-warfarin 7-hydroxylase present in human liver microsomes which appears to be responsible for the termination of warfarin's biological activity. Inhibition of the formation of (S)-7-hydroxywarfarin, the inactive, major metabolite of racemic warfarin in
Abdul Naveed Shaik et al.
Journal of pharmaceutical sciences, 105(6), 1976-1986 (2016-04-23)
The anticoagulant drug warfarin and the lipid-lowering statin drugs are commonly co-administered to patients with cardiovascular diseases. Clinically significant drug-drug interactions (DDIs) between these drugs have been recognized through case studies for many years, but the biochemical mechanisms causing these
Steven Lane et al.
British journal of clinical pharmacology, 73(1), 66-76 (2011-06-23)
Warfarin is a drug with a narrow therapeutic index and large interindividual variability in daily dosing requirements. Patients commencing warfarin treatment are at risk of bleeding due to excessive anticoagulation caused by overdosing. The interindividual variability in dose requirements is
Development of a method for the analysis of warfarin and metabolites in plasma and urine.
J X de Vries et al.
American clinical laboratory, 14(7), 20-21 (1995-06-07)
J F Darbyshire et al.
Drug metabolism and disposition: the biological fate of chemicals, 24(9), 1038-1045 (1996-09-01)
The effect of branch pathways on the observed intramolecular isotope effect and deuterium retention associated with 6- and 7-hydroxylation of selectively monodeuterated (R)- and (S)-warfarin with cytochrome P450 (CYP) 2C9 and CYP1A2 were studied. cDNA-expressed CYP2C9 was incubated with enantiomerically
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