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lepidine

Chemical Structure

General Material Information

Preferred name lepidine
Trivial Name 4-Methylquinoline
Short Description p-methylquinoline
Formula C10 H9 N
CAS Number 491-35-0
ECHA Number 207-734-2
FDA UNII 116169T3O8
Nikkaji Number J1.552K
Beilstein Number 0110926
MDL MFCD00006784
COE Number 488
Bio Activity Summary External link
NMR Predictor External link
FDA Mainterm 491-35-0 ; LEPIDINE
Synonyms
  • cincholepidine
  • 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-
  • 4-Methylquinoline
  • 4-Lepidine
  • Lepidin
  • γ-Methylquinoline
  • NSC 3412

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

4-methylquinoline
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:491-35-0
Pubchem (cid):10285
Pubchem (sid):134976471
Publications by PubMed
Dehydrogenative cross-coupling reaction by cooperative transition-metal and Brønsted acid catalysis for the synthesis of β-quinolinyl α-amino acid esters.
Biofunctional constituent isolated from Citrullus colocynthis fruits and structure-activity relationships of its analogues show acaricidal and insecticidal efficacy.
Antinociceptive effect of some biuret derivatives on formalin test in mice.
TiO₂ 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.
Antimicrobial potentials of active component isolated from Citrullus colocynthis fruits and structure-activity relationships of its analogues against foodborne bacteria.
Tafenoquine and NPC-1161B require CYP 2D metabolism for anti-malarial activity: implications for the 8-aminoquinoline class of anti-malarial compounds.
Anion effects on the structures and magnetic properties of binuclear lanthanide single-molecule magnets.
Genotoxicity risk assessment of diversely substituted quinolines using the SOS chromotest.
7-Hydroxyquinoline-8-carbaldehydes. 1. Ground- and excited-state long-range prototropic tautomerization.
A novel approach to the pyridoacridine ring system: synthesis of the topoisomerase inhibitor 13-deazaascididemin.
Integrated organic-aqueous biocatalysis and product recovery for quinaldine hydroxylation catalyzed by living recombinant Pseudomonas putida.
One-pot synthesis of pyranocoumarins via microwave-assisted pseudo multicomponent reactions and their molecular switching properties.
Synthesis, DNA binding, and oxidative cleavage studies of Fe(II) and Co(III) complexes containing bioactive ligands.
Synthesis, antidepressant and antifungal evaluation of novel 2-chloro-8-methylquinoline amine derivatives.
Physicochemical characterization of NPC 1161C, a novel antimalarial 8-aminoquinoline, in solution and solid state.
Separation and preconcentration of trace amounts of aluminum ions in surface water samples using different analytical techniques.
Spectroscopic studies on 2-[2-(4-methylquinolin-2-yl)hydrazono]-1,2-diphenylethanone molecule and its metal complexes.
A bistable molecular switch driven by photoinduced hydrogen-atom transfer.
An ATP-sensitive potassium channel blocker suppresses sodium-induced hypertension through increased secretion of urinary kallikrein.
Thiazole Orange derivatives: synthesis, fluorescence properties, and labeling cancer cells.
Toxicity in rhesus monkeys following administration of the 8-aminoquinoline 8-[(4-amino-l-methylbutyl)amino]- 5-(l-hexyloxy)-6-methoxy-4-methylquinoline (WR242511).
Selenium-containing heterocycles: synthesis and pharmacological activities of some new 4-methylquinoline-2(1H) selenone derivatives.
Facile, one-step production of niacin (vitamin B3) and other nitrogen-containing pharmaceutical chemicals with a single-site heterogeneous catalyst.
Evaluation of the Spanish hot dip galvanising sector as a source of polychlorinated dibenzo-p-dioxins and polychlorinated dibenzofurans.
Detection of methylquinoline transformation products in microcosm experiments and in tar oil contaminated groundwater using LC-NMR.
Synthesis of para-methoxybenzyl (PMB) ethers under neutral conditions.
Insertion reactions of alkynes and organic isocyanides into the palladium-carbon bond of dimetallic Fe-Pd alkoxysilyl complexes.
Development and validation of a stability-indicating reversed-phase high performance liquid chromatography method for NPC 1161C, a novel 8-aminoquinoline anti-malarial drug.
Ruthenium-catalyzed intermolecular coupling reactions of arylamines with ethylene and 1,3-dienes: mechanistic insight on hydroamination vs ortho-C-H bond activation.
Modulation of Ca(2+)-dependent and Ca(2+)-independent miniature endplate potentials by phorbol ester and adenosine in frog.
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.
[Antimicrobial effect of hydrazides and ilidenhydrazides of (quinoline-2-ilthio)carboxylic acids].
Ring-substituted quinolines. Part 2: Synthesis and antimycobacterial activities of ring-substituted quinolinecarbohydrazide and ring-substituted quinolinecarboxamide analogues.
Water-soluble molecular capsules: self-assembly and binding properties.
Synthesis and antimycobacterial activities of ring-substituted quinolinecarboxylic acid/ester analogues. Part 1.
Modular and tunable chemosensor scaffold for divalent zinc.
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.
Preparation of 7-alkylamino-2-methylquinoline-5,8-diones.
N-(2-hydroxypropyl)methacrylamide (HPMA) copolymers for targeted delivery of 8-aminoquinoline antileishmanial drugs.
Synthesis, characterization and reactions of 2-deoxo-5-deazaalloxazines.
A fluorometric assay for the determination of 1-deoxy-D-xylulose 5-phosphate synthase activity.
Derivatives of 8-hydroxy-2-methylquinoline are powerful prototypes for zinc sensors in biological systems.
A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes.
Synthesis and in vitro cytotoxicity of 2-alkylaminosubstituted quinoline derivatives.
Anti-mutagenic structural modification by fluorine-substitution in highly mutagenic 4-methylquinoline derivatives.
Sphingomonas sp. strain Lep1: an aerobic degrader of 4-methylquinoline.
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.
Evaluation of selected antiprotozoal drugs in the Babesia microti-hamster model.
Aerobic biodegradation of 4-methylquinoline by a soil bacterium.
Potent mutagenic potential of 4-methylquinoline: metabolic and mechanistic considerations.
Potential use of WR6026 as prophylaxis against transfusion-transmitted American trypanosomiasis.
Side-chain hydroxylation in the metabolism of 8-aminoquinoline antiparasitic agents.
Phase 2 efficacy trial of an oral 8-aminoquinoline (WR6026) for treatment of visceral leishmaniasis.
Hydroxylation and biodegradation of 6-methylquinoline by pseudomonads in aqueous and nonaqueous immobilized-cell bioreactors.
Microbial metabolism of quinoline and related compounds. XIX. Degradation of 4-methylquinoline and quinoline by Pseudomonas putida K1.
Microbial metabolism of quinoline and related compounds. XV. Quinoline-4-carboxylic acid oxidoreductase from Agrobacterium spec.1B: a molybdenum-containing enzyme.
Comparison of methemoglobin formers in protection against the toxic effects of cyanide.
Genotoxicity of fluoroquinolines and methylquinolines.
Pharmacokinetics of the anti-leishmanian agent WR 6026 in dogs.
Quinoline esters as potential antimalarial drugs: effect on relapses of Plasmodium cynomolgi infections in monkeys.
Microbial degradation of quinoline and methylquinolines.
Carcinogenicity of quinoline, 4- and 8-methylquinoline and benzoquinolines in newborn mice and rats.
2,2-Dialkyl-1,2-dihydroquinolines: cytochrome P-450 catalyzed N-alkylporphyrin formation, ferrochelatase inhibition, and induction of 5-aminolevulinic acid synthase activity.
Fungal metabolism of 4-methylprimaquine.
Metabolism of a potential 8-aminoquinoline antileishmanial drug in rat liver microsomes.
High-performance liquid chromatographic method for the analysis of a candidate 8-aminoquinoline antileishmanial drug using oxidative electrochemical detection.
Tumor-initiating activity of quinoline and methylated quinolines on the skin of SENCAR mice.
Study of artificial flavouring substances for mutagenicity in the Salmonella/microsome, Basc and micronucleus tests.
Quinoline and methylquinolines in cigarette smoke: comparative data and the effect of filtration.
Effect of carcinogenic components of cigarette smoke on in vivo production of murine interferon.
On the metabolism of quinoline and isoquinoline: possible molecular basis for differences in biological activities.
Microbial transformation of nitroaromatic compounds in sewage effluent.
Effect of sidestream tobacco smoke components on alpha/beta interferon production.
[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].
Synthesis and antimalarial activity of 8-[(1-alkyl-4-aminobutyl)amino]-6-methoxy-4-methylquinolines.
[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)].
Analogues of 8-[[6-(diethylamino) hexyl]amino]-6-methoxy-4-methylquinoline as candidate antileishmanial agents.
Synthesis of 2,4-disubstituted 6-methoxy-8-aminoquinoline analogues as potential antiparasitics.
Leishmaniasis: in search of new chemotherapeutic agents.
Primaquine analogues: derivatives of 4-amino-2-methoxyacridine.
[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)].
The antileishmanial activity of lepidines.
Toxic interaction of mixtures of two coal conversion effluent components (resorcinol and 6-methylquinoline) to Daphnia magna.
Antimalarials. 11. 2-Vinylogs of substituted 2-aryl-4-quinoline amino alcohols.
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.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB33437
FooDB:FDB011475
Export Tariff Code:2933.40.7050
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 143.18873596191
Specific gravity @ 25 °C
Pounds per Gallon 9.012 to 9.062
Refractive Index 1.615 to 1.621 @ 20 °C
Vapor Pressure 0.018 mmHg @ 25 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 2.61
Solubility
alcohol Yes
water, 479.2 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Burnt
burnt, oily, herbal, floral, sweet
General comment At 100.00 %. burnt oily herbal floral sweet
Flavor Type: Floral
sweet, floral, oily, burnt
General comment At 5.00 ppm in water. sweet floral oily slightly burnt

Occurrences

Potential Uses

Applications
Odor purposes Animal, Chypre, Leather, Rose, Woody
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 1260 mg/kg
(Moreno, 1976y)

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
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
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.400002.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.200001.00000
Edible ices, including sherbet and sorbet (03.0): 0.400002.00000
Processed fruit (04.1): 0.300001.50000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 0.400002.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.200001.00000
Bakery wares (07.0): 0.400002.00000
Meat and meat products, including poultry and game (08.0): 0.100000.40000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.100000.40000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.200001.00000
Foodstuffs intended for particular nutritional uses (13.0): 0.400002.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.200001.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): --
Ready-to-eat savouries (15.0): 1.000005.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.200001.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 24 (FGE.24): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)
View page or View pdf

Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28 Flavouring Group Evaluation 24, Revision 1 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 77 (FGE77) [1] - Consideration of Pyridine, Pyrrole and Quinoline Derivatives evaluated by JECFA (63rd meeting) structurally related to Pyridine, Pyrrole, Indole and Quinoline Derivatives evaluated by EFSA in FGE.24Rev1 (2008)
View page or View pdf

Scientific opinion on Flavouring Group Evaluation 24, Revision 2 (FGE.24Rev2): Pyridine, pyrrole, indole and quinoline derivatives from chemical group 28
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):491-35-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10285
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-methylquinoline
Chemidplus:0000491350
RTECS:OH0316000 for cas# 491-35-0