lepidine
p-methylquinoline
Identification
| Name | lepidine |
| IUPAC | 4-methylquinoline |
| CAS Number | 491-35-0 |
| EINECS | 207-734-2 |
| FDA UNII | 116169T3O8 |
| Molecular Formula | C10 H9 N |
| Molecular Weight | 143.18873000 |
| MDL Number | MFCD00006784 |
| Nikkaji Number | J1.552K |
| Beilstein | 0110926 |
| CoE Number | 488 |
| XlogP3 | 2.60 (est) |
Regulatory
| FDA Mainterm (SATF) | 491-35-0 ; LEPIDINE |
| FDA Regulation | FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION |
Physical Properties
| Appearance | colorless to yellow clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 1.08300 to 1.08900 @ 25.00 °C. |
| Pounds per Gallon - (est). | 9.012 to 9.062 |
| Refractive Index | 1.61500 to 1.62100 @ 20.00 °C. |
| Melting Point | 9.00 °C. @ 760.00 mm Hg |
| Boiling Point | 264.00 °C. @ 760.00 mm Hg |
| Vapor Pressure | 0.018000 mmHg @ 25.00 °C. (est) |
| Flash Point | > 230.00 °F. TCC ( > 110.00 °C. ) |
| logP (o/w) | 2.610 |
| Soluble in | alcohol |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Description | at 100.00 %. |
| Taste Description | at 5.00 ppm in water. |
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 1260 mg/kg |
| 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 | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| Recommendation for lepidine usage levels up to | 0.6000 % in the fragrance concentrate. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.12 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 160 (μg/person/day) |
| Threshold of Concern | 90 (μg/person/day) |
| Structure Class | III |
| Dairy products, excluding products of category 02.0 (01.0) | 0.40000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 0.20000 |
| Edible ices, including sherbet and sorbet (03.0) | 0.40000 |
| Processed fruit (04.1) | 0.30000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 0.40000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 0.20000 |
| Bakery wares (07.0) | 0.40000 |
| Meat and meat products, including poultry and game (08.0) | 0.10000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 0.10000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 0.20000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 0.40000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 0.20000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | - |
| Ready-to-eat savouries (15.0) | 1.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 0.20000 |
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Potential Uses
Natural Occurrence
Synonyms
cincholepidine
lepidine
4-
lepidine
4-
methyl quinoline
gamma-
methyl quinoline
p-
methyl quinoline
para-
methyl quinoline
4-
methylquinoline
gamma-
methylquinoline
p-
methylquinoline
para-
methylquinoline
quinoline, 4-methyl-
PubMed:
Dehydrogenative cross-coupling reaction by cooperative transition-metal and Brønsted acid catalysis for the synthesis of β-quinolinyl α-amino acid esters.
PubMed:
Biofunctional constituent isolated from Citrullus colocynthis fruits and structure-activity relationships of its analogues show acaricidal and insecticidal efficacy.
PubMed:
Antinociceptive effect of some biuret derivatives on formalin test in mice.
PubMed:
TiOâ nanotube arrays prepared by anodization as an adsorbent in micro-solid-phase extraction to preconcentrate and determine nitrogen-containing polycyclic aromatic hydrocarbons in water samples.
PubMed:
Antimicrobial potentials of active component isolated from Citrullus colocynthis fruits and structure-activity relationships of its analogues against foodborne bacteria.
PubMed:
Tafenoquine and NPC-1161B require CYP 2D metabolism for anti-malarial activity: implications for the 8-aminoquinoline class of anti-malarial compounds.
PubMed:
Anion effects on the structures and magnetic properties of binuclear lanthanide single-molecule magnets.
PubMed:
Genotoxicity risk assessment of diversely substituted quinolines using the SOS chromotest.
PubMed:
7-Hydroxyquinoline-8-carbaldehydes. 1. Ground- and excited-state long-range prototropic tautomerization.
PubMed:
A novel approach to the pyridoacridine ring system: synthesis of the topoisomerase inhibitor 13-deazaascididemin.
PubMed:
Integrated organic-aqueous biocatalysis and product recovery for quinaldine hydroxylation catalyzed by living recombinant Pseudomonas putida.
PubMed:
One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multicomponent reactions and their molecular switching properties.
PubMed:
Synthesis, DNA binding, and oxidative cleavage studies of Fe(II) and Co(III) complexes containing bioactive ligands.
PubMed:
Synthesis, antidepressant and antifungal evaluation of novel 2-chloro-8-methylquinoline amine derivatives.
PubMed:
Physicochemical characterization of NPC 1161C, a novel antimalarial 8-aminoquinoline, in solution and solid state.
PubMed:
Separation and preconcentration of trace amounts of aluminum ions in surface water samples using different analytical techniques.
PubMed:
Spectroscopic studies on 2-[2-(4-methylquinolin-2-yl)hydrazono]-1,2-diphenylethanone molecule and its metal complexes.
PubMed:
A bistable molecular switch driven by photoinduced hydrogen-atom transfer.
PubMed:
An ATP-sensitive potassium channel blocker suppresses sodium-induced hypertension through increased secretion of urinary kallikrein.
PubMed:
Thiazole Orange derivatives: synthesis, fluorescence properties, and labeling cancer cells.
PubMed:
Toxicity in rhesus monkeys following administration of the 8-aminoquinoline 8-[(4-amino-l-methylbutyl)amino]- 5-(l-hexyloxy)-6-methoxy-4-methylquinoline (WR242511).
PubMed:
Selenium-containing heterocycles: synthesis and pharmacological activities of some new 4-methylquinoline-2(1H) selenone derivatives.
PubMed:
Facile, one-step production of niacin (vitamin B3) and other nitrogen-containing pharmaceutical chemicals with a single-site heterogeneous catalyst.
PubMed:
Evaluation of the Spanish hot dip galvanising sector as a source of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans.
PubMed:
Detection of methylquinoline transformation products in microcosm experiments and in tar oil contaminated groundwater using LC-NMR.
PubMed:
Synthesis of para-methoxybenzyl (PMB) ethers under neutral conditions.
PubMed:
Insertion reactions of alkynes and organic isocyanides into the palladium-carbon bond of dimetallic Fe-Pd alkoxysilyl complexes.
PubMed:
Development and validation of a stability-indicating reversed-phase high performance liquid chromatography method for NPC 1161C, a novel 8-aminoquinoline anti-malarial drug.
PubMed:
Ruthenium-catalyzed intermolecular coupling reactions of arylamines with ethylene and 1,3-dienes: mechanistic insight on hydroamination vs ortho-C-H bond activation.
PubMed:
Modulation of Ca(2+)-dependent and Ca(2+)-independent miniature endplate potentials by phorbol ester and adenosine in frog.
PubMed:
Simultaneous determination of NSO-heterocycles, homocycles and their metabolites in groundwater of tar oil contaminated sites using LC with diode array UV and fluorescence detection.
PubMed:
[Antimicrobial effect of hydrazides and ilidenhydrazides of (quinoline-2-ilthio)carboxylic acids].
PubMed:
Ring-substituted quinolines. Part 2: Synthesis and antimycobacterial activities of ring-substituted quinolinecarbohydrazide and ring-substituted quinolinecarboxamide analogues.
PubMed:
Water-soluble molecular capsules: self-assembly and binding properties.
PubMed:
Synthesis and antimycobacterial activities of ring-substituted quinolinecarboxylic acid/ester analogues. Part 1.
PubMed:
Modular and tunable chemosensor scaffold for divalent zinc.
PubMed:
Gene cluster of Arthrobacter ilicis Ru61a involved in the degradation of quinaldine to anthranilate: characterization and functional expression of the quinaldine 4-oxidase qoxLMS genes.
PubMed:
Preparation of 7-alkylamino-2-methylquinoline-5,8-diones.
PubMed:
N-(2-hydroxypropyl)methacrylamide (HPMA) copolymers for targeted delivery of 8-aminoquinoline antileishmanial drugs.
PubMed:
Synthesis, characterization and reactions of 2-deoxo-5-deazaalloxazines.
PubMed:
A fluorometric assay for the determination of 1-deoxy-D-xylulose 5-phosphate synthase activity.
PubMed:
Derivatives of 8-hydroxy-2-methylquinoline are powerful prototypes for zinc sensors in biological systems.
PubMed:
A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes.
PubMed:
Synthesis and in vitro cytotoxicity of 2-alkylaminosubstituted quinoline derivatives.
PubMed:
Anti-mutagenic structural modification by fluorine-substitution in highly mutagenic 4-methylquinoline derivatives.
PubMed:
Sphingomonas sp. strain Lep1: an aerobic degrader of 4-methylquinoline.
PubMed:
Synthesis of Pyrrolo[4,3,2-de]quinolines from 6,7-Dimethoxy-4-methylquinoline. Formal Total Syntheses of Damirones A and B, Batzelline C, Isobatzelline C, Discorhabdin C, and Makaluvamines A-D.
PubMed:
Evaluation of selected antiprotozoal drugs in the Babesia microti-hamster model.
PubMed:
Aerobic biodegradation of 4-methylquinoline by a soil bacterium.
PubMed:
Potent mutagenic potential of 4-methylquinoline: metabolic and mechanistic considerations.
PubMed:
Potential use of WR6026 as prophylaxis against transfusion-transmitted American trypanosomiasis.
PubMed:
Side-chain hydroxylation in the metabolism of 8-aminoquinoline antiparasitic agents.
PubMed:
Phase 2 efficacy trial of an oral 8-aminoquinoline (WR6026) for treatment of visceral leishmaniasis.
PubMed:
Hydroxylation and biodegradation of 6-methylquinoline by pseudomonads in aqueous and nonaqueous immobilized-cell bioreactors.
PubMed:
Microbial metabolism of quinoline and related compounds. XIX. Degradation of 4-methylquinoline and quinoline by Pseudomonas putida K1.
PubMed:
Microbial metabolism of quinoline and related compounds. XV. Quinoline-4-carboxylic acid oxidoreductase from Agrobacterium spec.1B: a molybdenum-containing enzyme.
PubMed:
Comparison of methemoglobin formers in protection against the toxic effects of cyanide.
PubMed:
Genotoxicity of fluoroquinolines and methylquinolines.
PubMed:
Pharmacokinetics of the anti-leishmanian agent WR 6026 in dogs.
PubMed:
Quinoline esters as potential antimalarial drugs: effect on relapses of Plasmodium cynomolgi infections in monkeys.
PubMed:
Microbial degradation of quinoline and methylquinolines.
PubMed:
Carcinogenicity of quinoline, 4- and 8-methylquinoline and benzoquinolines in newborn mice and rats.
PubMed:
2,2-Dialkyl-1,2-dihydroquinolines: cytochrome P-450 catalyzed N-alkylporphyrin formation, ferrochelatase inhibition, and induction of 5-aminolevulinic acid synthase activity.
PubMed:
Fungal metabolism of 4-methylprimaquine.
PubMed:
Metabolism of a potential 8-aminoquinoline antileishmanial drug in rat liver microsomes.
PubMed:
High-performance liquid chromatographic method for the analysis of a candidate 8-aminoquinoline antileishmanial drug using oxidative electrochemical detection.
PubMed:
Tumor-initiating activity of quinoline and methylated quinolines on the skin of SENCAR mice.
PubMed:
Study of artificial flavouring substances for mutagenicity in the Salmonella/microsome, Basc and micronucleus tests.
PubMed:
Quinoline and methylquinolines in cigarette smoke: comparative data and the effect of filtration.
PubMed:
Effect of carcinogenic components of cigarette smoke on in vivo production of murine interferon.
PubMed:
On the metabolism of quinoline and isoquinoline: possible molecular basis for differences in biological activities.
PubMed:
Microbial transformation of nitroaromatic compounds in sewage effluent.
PubMed:
Effect of sidestream tobacco smoke components on alpha/beta interferon production.
PubMed:
[Antimalarial 6-aminoquinolines. XIV. 6-(4-Diethylamino-1-methylbutylamino)-4-methoxy-2-methyl- and -2,4-dimethylquinolines with variations of substituents in positions 5 and 8].
PubMed:
Synthesis and antimalarial activity of 8-[(1-alkyl-4-aminobutyl)amino]-6-methoxy-4-methylquinolines.
PubMed:
[Antimalarial 6-aminoquinolines. XIII. 5,8-Dialkoxyderivatives of 6-(4-diethylamino-1-methylbutylamino)-2-methyl- and 6-(4-diethylamino-1-methylbutylamino)-2,4-dimethylquinoline (author's transl)].
PubMed:
Analogues of 8-[[6-(diethylamino) hexyl]amino]-6-methoxy-4-methylquinoline as candidate antileishmanial agents.
PubMed:
Synthesis of 2,4-disubstituted 6-methoxy-8-aminoquinoline analogues as potential antiparasitics.
PubMed:
Leishmaniasis: in search of new chemotherapeutic agents.
PubMed:
Primaquine analogues: derivatives of 4-amino-2-methoxyacridine.
PubMed:
[The reaction of heteroaromatic N-oxide with acid chloride and cyanide. IX. On p-tolylsulfonylation on side-chain carbon in 2-methylquinoline 1-oxide and related compounds (author's transl)].
PubMed:
The antileishmanial activity of lepidines.
PubMed:
Toxic interaction of mixtures of two coal conversion effluent components (resorcinol and 6-methylquinoline) to Daphnia magna.
PubMed:
Antimalarials. 11. 2-Vinylogs of substituted 2-aryl-4-quinoline amino alcohols.
PubMed:
Chichibabin reaction. 3. Chichibabin reaction of 7-methylquinoline and migration of the methyl group in Friedel-Crafts reaction of N-(m-tolyl)- and N-)p-tolyl)-beta-chloropropionamide (studies on the syntheses of heterocyclic compounds. CCXV.