139239-49-9

Basic information

• Product Name: (9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate
• Synonyms: (9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate;9-Acetyl Apoquinidine Methyl Ether
• CAS NO: 139239-49-9
• Molecular Formula: C₂₂H₂₆N₂O₃
• Molecular Weight: 366.458
• Product Categories: Chiral Reagents
• Mol File: 139239-49-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 178-180°C
• Appearance: yellow solid
• Storage Temp.: Refrigerator
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: (9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate(139239-49-9)
• EPA Substance Registry System: (9S)- 3,10-Didehydro-10,11-dihydro-6'-methoxycinchonan-9-ol Acetate(139239-49-9)

Safety Data

• Hazardous Substances Data: 139239-49-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

A synthetic quinidine derivative

Upstream product

• 108-24-7 acetic anhydride 
• 139237-97-1 (S)-((2R)-5-ethylidene-1-azabicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinoline-4-yl)-methanol 
• 56-54-2 (+)-quinidine 
• 53922-99-9 α-10-bromodihydroquinidine 

Downstream Products

• 60723-43-5 (8R,9S)-6'-methoxy-3-oxoruban-9-yl acetate 
• 60723-44-6 (3S)-3-hydroxyquinidine 9-benzoate 
• 60761-51-5 (3R)-3-hydroxyquinidine 
• 53467-23-5 3-hydroxyquinidine 

Relevant articles and documents

(3S)-3-Hydroxyquinidine, the Major Biotransformation Product of Quinidine. Synthesis and Conformational Studies. X-Ray Molecular Structure of (3S)-3-Hydroxyquinidine Methanesulphonate

(3S)-3-Hydroxyquinidine, the major metabolite of the Cinchona alkaloid quinidine, was prepared by synthetic chemical modification or microbial oxidation of quinidine.The structure of this metabolite has been demonstrated to be (3S)-3-hydroxyquinidine by 1H and 13C NMR, IR, UV and mass spectral analysis.Previously published comparisons of the 13C NMR spectra of 3-hydroxyquinidine and model compounds were used to establish the absolute stereochemistry of the metabolite (see ref. 8).This assignment has been verified by single-crystal X-ray analysis of (3S)-3-hydroxyquinidine methanesulphonate.The gas- and solution-phase conformational preference of the metabolite derived from molecular modelling and NOE studies are compared with the conformation observed by X-ray crystallography.