14528-51-9

Basic information

• Product Name: (8alpha)-6'-methoxycinchonan
• Synonyms: (8alpha)-6'-methoxycinchonan;EINECS 238-547-4;(8α)-6'-Methoxycinchonan;Deoxyquinine
• CAS NO: 14528-51-9
• Molecular Formula: C₂₀H₂₄N₂O
• Molecular Weight: 308.41736
• EINECS: 238-547-4
• Mol File: 14528-51-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 450.8°Cat760mmHg
• Flash Point: 226.4°C
• Appearance: /
• Density: 1.14g/cm³
• CAS DataBase Reference: (8alpha)-6'-methoxycinchonan(CAS DataBase Reference)
• NIST Chemistry Reference: (8alpha)-6'-methoxycinchonan(14528-51-9)
• EPA Substance Registry System: (8alpha)-6'-methoxycinchonan(14528-51-9)

Safety Data

• Hazardous Substances Data: 14528-51-9(Hazardous Substances Data)

Usage

General Description

(8alpha)-6'-methoxycinchonan is a chemical compound belonging to the cinchona alkaloid family. It is derived from the bark of the cinchona tree and is known for its antimalarial properties. The compound has a molecular formula of C20H24N2O2 and a molecular weight of 336.42 g/mol. It is a natural product that has been used for centuries in traditional medicine to treat fevers and malaria. Its medicinal properties are attributed to its ability to inhibit the growth of the malaria parasite. The compound has also been studied for its potential anti-inflammatory and analgesic effects. Additionally, it has been used as a building block for the synthesis of other bioactive compounds.

Upstream product

• 339046-93-4 (4S,5R)-5-Azidomethyl-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(6-methoxy-quinolin-4-yl)-hept-6-en-2-one 
• 339046-95-6 4-{(2S,4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-piperidin-2-ylmethyl}-6-methoxy-quinoline 
• 339046-94-5 4-{(4R,5R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-vinyl-3,4,5,6-tetrahydro-pyridin-2-ylmethyl}-6-methoxy-quinoline 
• 339046-88-7 (3R,4R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-vinyl-dihydro-furan-2-one 
• 339046-86-5 3-(tert-butyl-dimethyl-silanyloxymethyl)-pent-4-enoic acid diethylamide 
• 339046-99-0 (S)-3-Hydroxymethyl-pent-4-enoic acid diethylamide 
• 107080-45-5 (S)-(+)-β-vinyl-γ-butyrolactone 
• 41037-26-7 6-methoxy-4-methylquinoline 
• 339046-87-6 3-(tert-butyl-dimethyl-silanyloxymethyl)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-pent-4-enoic acid diethylamide 
• 339046-98-9 (2R,3R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-hydroxymethyl-pent-4-enoic acid diethylamide 
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• 130-95-0 Quinine 
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• 339046-91-2 (3S,4R)-4-Azidomethyl-3-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-hex-5-enal 

Downstream Products

• 130-95-0 quinine 

Relevant articles and documents

Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups

We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.

The hydroxyl functionality and a rigid proximal N are required for forming a novel non-covalent quinine-heme complex

Quinoline antimalarial drugs bind both monomeric and dimeric forms of free heme, with distinct preferences depending on the chemical environment. Under biological conditions, chloroquine (CQ) appears to prefer to bind to μ-oxo dimeric heme, while quinine (QN) preferentially binds monomer. To further explore this important distinction, we study three newly synthesized and several commercially available QN analogues lacking various functional groups. We find that removal of the QN hydroxyl lowers heme affinity, hemozoin (Hz) inhibition efficiency, and antiplasmodial activity. Elimination of the rigid quinuclidyl ring has similar effects, but elimination of either the vinyl or methoxy group does not. Replacing the quinuclidyl N with a less rigid tertiary aliphatic N only partially restores activity. To further study these trends, we probe drug-heme interactions via NMR studies with both Fe and Zn protoporphyrin IX (FPIX, ZnPIX) for QN, dehydroxyQN (DHQN), dequinuclidylQN (DQQN), and deamino-dequinuclidylQN (DADQQN). Magnetic susceptibility measurements in the presence of FPIX demonstrate that these compounds differentially perturb FPIX monomer-dimer equilibrium. We also isolate the QN-FPIX complex formed under mild aqueous conditions and analyze it by mass spectrometry, as well as fluorescence, vibrational, and solid-state NMR spectroscopies. The data elucidate key features of QN pharmacology and allow us to propose a refined model for the preferred binding of QN to monomeric FPIX under biologically relevant conditions. With this model in hand, we also propose how QN, CQ, and amodiaquine (AQ) differ in their ability to inhibit Hz formation.

PHOTOREACTIONS OF QUININE IN AQUEOUS CITRIC ACID SOLUTION. PART 3. PRODUCTS FORMED IN AQUEOUS 2-HYDROXY-2-METHYLPROPIONIC ACID

7'-(2-hydroxyprop-2-yl)-7',8'-dihydroquinine and the corresponding 7',8'-dihydrodeoxyquinine derivative have been identified together with deoxyquinine as products of the irradation of quinine in aqueous 2-hydroxy-2-methylpropionic acid.A cyclised product of 4'-(2-hydroxyprop-2-yl)-1',4'-dihydroquinine was also isolated from the reaction mixture.