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5543-58-8

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5543-58-8 Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 5543-58-8 differently. You can refer to the following data:
1. (R)-(+)-warfarin has been used to investigate whether enantiomers of warfarin stereoselectively interact with pregnane X nuclear receptor (PXR) to upregulate main drug/xenobiotic-metabolizing enzymes cytochrome P450 3A4 (CYP3A4) and cytochrome P450 2C9 (CYP2C9). It has also been used in HepG2 cells to study protein profiles
2. The R-(+)-form of Warfarin (W498500). Coumarin anticoagulant.

General Description

The chiral carbon at position 9 produces two enantiomers, R- and S-warfarin. Commercially available warfarin (Coumadin or Jantoven) is a racemic mixture of S- and R-enantiomers.

Biochem/physiol Actions

Warfarin acts as a vitamin K antagonist. It is widely used to treat thromboembolic disorders. (R)-warfarin interacts with pregnane X receptor (PXR) and induces cytochrome P450 3A4 (CYP3A4) and CYP2C9 mRNAs expression in primary human hepatocyte cultures.

Check Digit Verification of cas no

The CAS Registry Mumber 5543-58-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,5,4 and 3 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 5543-58:
(6*5)+(5*5)+(4*4)+(3*3)+(2*5)+(1*8)=98
98 % 10 = 8
So 5543-58-8 is a valid CAS Registry Number.
InChI:InChI=1/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3/t15-/m1/s1

5543-58-8 Well-known Company Product Price

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  • Sigma

  • (UC213)  (R)-(+)-Warfarin  ≥97% (HPLC)

  • 5543-58-8

  • UC213-10MG

  • 13,759.20CNY

  • Detail

5543-58-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-warfarin

1.2 Other means of identification

Product number -
Other names (R)-(+)-WARFARIN

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5543-58-8 SDS

5543-58-8Relevant articles and documents

Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

Bencivenni, Giorgio,Calcaterra, Andrea,Ciogli, Alessia,Iazzetti, Antonia,Mazzoccanti, Giulia,Righi, Paolo,Villani, Claudio

supporting information, (2021/12/01)

The field of organocatalysis is expanding at a fast pace. Its growth is sustained by major stimuli, such as the effort toward an understanding of the mechanisms of reaction and catalytic processes in general, the elucidation of basic properties leading to stereocontrol and the search for broad applicability and scalability of the synthetic methodology. This paper reports a thorough study based on ESI-MS spectrometry of amino-organocatalyzed model reactions under different experimental conditions. Off-line reaction monitoring of mixtures containing different catalytic systems, by ESI-MSn showed the presence of several putative intermediate species, either in their protonated or sodiated forms. In addition, enantioselective chromatography of crude reactions provides the stereochemical outcome of asymmetric reactions. The bulk of the data collected offers a clue of the intricate pathways occurring in solution for the studied reactions.

Enantioselective Michael Addition Reaction Catalysed by Enantiopure Binuclear Nickel(II) Close-Ended Helicates

Arunachalam, Rajendran,Chinnaraja, Eswaran,Natarajan, Ramalingam,Samanta, Krishanu,Subramanian, Palani S.

, (2020/02/04)

The enantiopure Ni(II) helicates [Ni2L1RR.Cl2] (1), [Ni2L1SS.Cl2] (1′), [Ni2L2RR.Cl2] (2), [Ni2L2SS.Cl2] (2′) were synthesized by one-pot self-assembly technique from R-(+)- or S-(?)-1,1′-binaphthyl-2,2′-diamine, with 4-methyl-2,6-diformyl phenol or 4-tert-butyl-2,6-diformyl phenol and nickel salts. This binuclear double stranded Ni(II) helicates were characterized by ESI-MS, IR and single crystal X-ray structure wherever applicable. The extensive chiroptical studies suggest that the complexes are enantiopure in nature. The chirality transfer from ligand L1RR & L2RR to Ni(II) metal centre produced ΔΔ geometrical chirality, while their enantiomeric counterpart L1SS & L2SS produced ΛΛ chirality in their respective complexes.These enantiopure helicates were applied as catalysts in asymmetric Michael addition of 1,3-dicarbonyl compounds with β-nitrostyrene to produce nitroalkanes in good yield (96–98%) and ee (78–94%). (Figure presented.).

A Silica-Supported Catalyst Containing 9-Amino-9-deoxy-9-epi-quinine and a Benzoic Acid Derivative for Stereoselective Batch and Flow Heterogeneous Reactions

Ciogli, Alessia,Capitani, Donatella,Di Iorio, Nicola,Crotti, Simone,Bencivenni, Giorgio,Donzello, Maria Pia,Villani, Claudio

, p. 2020 - 2028 (2019/03/07)

A heterogeneous, silica-based catalyst containing 9-amino-9-deoxy-epi-quinine (or quinidine) and a derivative of benzoic acid was synthesized through radical thiol-ene click reaction. The acid component allows the in situ activation of cinchona amino group, acting as a bifunctional catalyst. The heterogenized catalysts efficiently promoted the reaction of ketones with trans-β-nitrostyrene, with diastereo- and enantioselectivity comparable to those of the homogeneous counterparts (dr up to 90:10 and 90 % ee). In addition, the catalyst retained a constant activity for at least four cycles. Finally, the supported catalyst (9-amino-9-deoxy-epi-quinine/achiral acid) was employed under continuous-flow conditions. Two enantioselective Michael reactions were in sequence performed with the same homemade packed-bed reactor. The addition of cyclohexanone to trans-β-nitrostyrene provided the evaluation of optimal residence time with high level of stereoselection (2 μL/min flow rate, 83 % ee). Furthermore, the flow reactor well performed in the preparation of warfarin (isolated yield 95 %, 78 % ee. in 16 h at room temperature). The dual (chiral amine/achiral acid) solid supported system, making an even easier work-out, represents a valuable tool for green chemistry and is attractive for large scale applications.

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