6-methoxyquinoline
quinoline, 6-methoxy-
Identification
| Name | 6-methoxyquinoline |
| IUPAC | 6-methoxyquinoline |
| CAS Number | 5263-87-6 |
| EINECS | 226-077-2 |
| FDA UNII | 5S1U3125AD |
| Molecular Formula | C10 H9 N O |
| Molecular Weight | 159.18793000 |
| MDL Number | MFCD00006800 |
| Nikkaji Number | J54.285G |
| Beilstein | 0115244 |
| XlogP3 | 2.20 (est) |
Regulatory
| JECFA Food Flavoring | 2157 6-methoxyquinoline |
| FEMA Number | 4640 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 5263-87-6 ; 6-METHOXYQUINOLINE |
Physical Properties
| Appearance | colorless to pale yellow clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 1.15100 to 1.15400 @ 20.00 °C. |
| Pounds per Gallon - (est). | 9.589 to 9.614 |
| Refractive Index | 1.62200 to 1.62500 @ 20.00 °C. |
| Melting Point | 19.00 to 24.00 °C. @ 760.00 mm Hg |
| Boiling Point | 140.00 to 146.00 °C. @ 15.00 mm Hg, 294.00 to 296.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.003000 mmHg @ 25.00 °C. (est) |
| Flash Point | > 230.00 °F. TCC ( > 110.00 °C. ) |
| logP (o/w) | 2.200 |
| Soluble in | alcohol |
| Insoluble in | water |
No sensory data available
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for 6-methoxyquinoline usage levels up to | not for fragrance use. |
| baked goods | 0.50000 |
| beverages(nonalcoholic) | - |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | 0.50000 |
| fish products | - |
| frozen dairy | - |
| fruit ices | - |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | 0.50000 |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
6-
methoxy quinoline
methyl 6-quinolyl ether
methyl quinolin-6-yl ether
quinoline, 6-methoxy-
PubMed:
Effect of nanosize micelles of ionic and neutral surfactants on the photophysics of protonated 6-methoxyquinoline: Time-resolved fluorescence study.
PubMed:
Supramolecular study, Hirshfeld analysis and theoretical study of 6-methoxyquinoline N-oxide dihydrate.
PubMed:
Dissociation kinetic analysis of Ce(III) complex with Quin2 by microchip capillary electrophoretic reactor.
PubMed:
Methoxyquinoline labeling--a new strategy for the enantioseparation of all chiral proteinogenic amino acids in 1-dimensional liquid chromatography using fluorescence and tandem mass spectrometric detection.
PubMed:
5-Amino-2-aroylquinolines as highly potent tubulin polymerization inhibitors. Part 2. The impact of bridging groups at position C-2.
PubMed:
Ratiometric fluorescence imaging for distinguishing chloride concentration between normal and ischemic ventricular myocytes.
PubMed:
Methoxyquinoline-diethylenetriamine conjugate as a fluorescent zinc sensor.
PubMed:
Factors controlling adsorption equilibria from solution onto solid surfaces: the uptake of cinchona alkaloids on platinum surfaces.
PubMed:
Competitive chemisorption between pairs of cinchona alkaloids and related compounds from solution onto platinum surfaces.
PubMed:
Kinetic isotope effects implicate a single oxidant for cytochrome P450-mediated O-dealkylation, N-oxygenation, and aromatic hydroxylation of 6-methoxyquinoline.
PubMed:
Direct measurement of free chloride concentrations in the phagolysosomes of human neutrophils.
PubMed:
A microchip capillary electrophoretic reactor: a new methodology for direct measurement of dissociation kinetics of metal complexes.
PubMed:
Application of GC-EI-MS for the identification and investigation of positional isomer in primaquine, an antimalarial drug.
PubMed:
Boronic acid fluorescent sensors for monosaccharide signaling based on the 6-methoxyquinolinium heterocyclic nucleus: progress toward noninvasive and continuous glucose monitoring.
PubMed:
Entropy-controlled solvolytic dissociation kinetics of lanthanide(III) complexes with polyaminocarboxylates in aqueous solutions.
PubMed:
Chloride-sensitive fluorescent indicators.
PubMed:
Requirement of intracellular calcium mobilization for peroxynitrite-induced poly(ADP-ribose) synthetase activation and cytotoxicity.
PubMed:
Dipeptide derivatives of primaquine as transmission-blocking antimalarials: effect of aliphatic side-chain acylation on the gametocytocidal activity and on the formation of carboxyprimaquine in rat liver homogenates.
PubMed:
Effects of subtilisin cleavage of monomeric actin on its nucleotide binding.
PubMed:
Hydrolysis kinetics of photoexcited 6-methoxyquinoline in aqueous acetonitrile solutions.
PubMed:
Side-chain hydroxylation in the metabolism of 8-aminoquinoline antiparasitic agents.
PubMed:
Peroxidation of the antimalarial drug primaquine: characterization of a benzidine-like metabolite with methaemoglobin-forming activity.
PubMed:
Stopped-flow studies of calcium dissociation from calcium-binding-site mutants of Drosophila melanogaster calmodulin.
PubMed:
Structure of the anti-malarial drug primaquine diphosphate.
PubMed:
Effects of an NADPH-generating system on primaquine degradation by hamster liver fractions.
PubMed:
Methemoglobin formation resulting from administration of candidate 8-aminoquinoline antiparasitic drugs in the dog.
PubMed:
[In Process Citation].
PubMed:
Carrier-linked primaquine in the chemotherapy of malaria.
PubMed:
Characterization of the urinary metabolites of primaquine in rats.
PubMed:
Fluorimetric detection of tautomeric equilibria in 8-aminoquinolines.
PubMed:
Excretion, distribution, and metabolism of primaquine in rats.
PubMed:
Metabolism and distribution of primaquine in monkeys.
PubMed:
Synthesis of 8-(3-Carboxy-l-methyl-propylammo)-6-methoxyquinoline: A Newly Characterized Primaquine Metabolite.
PubMed:
Production of a novel dimeric metabolite of primaquine by Streptomyces rimosus.
PubMed:
Synthesis of certain hydroxy analogues of the antimalarial drug primaquine and their in vitro methemoglobin-producing and glutathione-depleting activity in human erythrocytes.
PubMed:
High-performance liquid chromatographic analysis of the metabolism of primaquine and the identification of a new mammalian metabolite.
PubMed:
Primaquine: metabolism by microorganisms and 13C nuclear magnetic resonance assignments.
PubMed:
The activity against Trypanosoma cruzi and cutaneous leishmaniasis, and toxicity, of moxipraquine (349C59).
PubMed:
Synthesis of some 4-substituted 8-amino-6-methoxyquinolines as potential antimalarials.
PubMed:
Fluorescence of 6-methoxyquinoline, quinine, and quinidine in aqueous media.
PubMed:
Inhibition of liver alcohol dehydrogenase by primaquine and 8-amino-6-methoxyquinoline compounds.
PubMed:
[Action of 20-methyl-4-mercapto-6-methoxyquinoline on in vitro fibroblast cultures].
PubMed:
[Action of 2-methyl-4-mercapto-6-methoxyquinoline on in vitro cultures of human tumor cells of the KB strain].
PubMed:
Chemotherapy of experimental trypanosomiasis; trypanocidal activity of certain bis (2-methyl-4-amino-6-quinolyl) amides and ethers.
PubMed:
Synthesis of 5-substituted derivatives of 6-methoxy-8-aminoquinoline and of 5-chloro-6-methoxyquinoline.
PubMed:
Heterocyclic basic compounds; 8-[3-(3'-aminopropylamino)-propylamino]-6-methoxyquinoline.
PubMed:
8-[3-(3'-Aminopropylamino)-propylamino]-6-methoxyquinoline.
PubMed:
Synthetic antimalarials; 8-(5-isopropylaminoamylamino)-6-methoxyquinoline (SW-13,276) and some related compounds.