66556-78-3

Basic information

• Product Name: (S)-(-)-Nicoumalone
• Synonyms: (S)-(-)-Nicoumalone
• CAS NO: 66556-78-3
• Molecular Formula: C₁₉H₁₅NO₆
• Molecular Weight: 353.328
• Product Categories: Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 66556-78-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 546.9 °C at 760 mmHg
• Flash Point: 284.6 °C
• Appearance: /
• Density: 1.427 g/cm³
• Vapor Pressure: 8.54E-13mmHg at 25°C
• Refractive Index: 1.656
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: (S)-(-)-Nicoumalone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-Nicoumalone(66556-78-3)
• EPA Substance Registry System: (S)-(-)-Nicoumalone(66556-78-3)

Safety Data

• Hazardous Substances Data: 66556-78-3(Hazardous Substances Data)

Usage

Description

(S)-(-)-Nicoumalone, also known as (S)-Acenocoumarol, is the S-enantiomer of Acenocoumarol, a short-lived oral anti-coagulant. It functions by inhibiting vitamin K epoxide reductase, similar to warfarin, but has a higher intrinsic anticoagulant potency. The S-enantiomer has a shorter plasma elimination half-life and faster plasma clearance compared to the R-enantiomer. Due to its pharmacokinetic characteristics, (S)-(-)-Nicoumalone is less potent in vivo as an anti-coagulant than the R-enantiomer.
Used in Pharmaceutical Industry:
(S)-(-)-Nicoumalone is used as an anti-coagulant agent for the prevention and treatment of blood clots and related conditions. Its higher intrinsic potency and faster clearance make it a suitable alternative to other anti-coagulants like warfarin and phenprocoumon. However, its lower in vivo potency compared to the R-enantiomer should be considered when determining the appropriate dosage and treatment regimen.

InChI:InChI=1/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,23H,10H2,1H3/t15-/m0/s1

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 946-49-6 (E)-4-(4-nitrophenyl)-3-buten-2-one 
• 946-49-6 4-(p-nitrophenyl)-3-butene-2-one 
• 555-16-8 4-nitrobenzaldehdye 

Relevant articles and documents

A bis-Lewis basic 2-aminoDMAP/prolinamide organocatalyst for application to the enantioselective synthesis of Warfarin and derivatives

A new chiral sec-amine/amidine-base hybrid catalyst, 2-aminoDMAP/prolinamide, is reported, which is able to catalyze conjugate addition of 4-hydroxycoumarin and various benzylideneacetones, a reaction that directly gives anticoagulant Warfarin and its analogues, with good yields (70-87%) and enantioselectivities (58-72%).

Asymmetric synthesis of warfarin and its analogues on water

The asymmetric Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones on water without organic co-solvents is reported to be catalysed by organic primary amines. The application of enantiomerically pure (S,S)-diphenylethylenediamine affords a series of important pharmaceutically active compounds in good to excellent yields (73-98%) and with good enantioselectivities (up to 76% ee) via reactions accelerated by ultrasound. In particular, our developments led to an efficient protocol for the 'solids on water' formation of the anticoagulant warfarin in both enantiomeric forms. The presented scalable and environmentally friendly organocatalytic approach affords the target drug in enantiomerically pure form.

Highly enantioselective synthesis of Warfarin and its analogs catalysed by primary amine-phosphinamide bifunctional catalysts

An efficient enantioselective Michael addition of 4-hydroxycoumarin to α,β-unsaturated ketones catalysed by primary amine-phosphinamide bifunctional catalysts has been developed. This reaction afforded Warfarin and its analogs in moderate to excellent yie