2-methyl piperidine
2-methylpiperidine
 
Notes:
Used as a food additive [EAFUS]
  • Penta International
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      For over 30 years, Penta Manufacturing Company has played a growing role in worldwide chemistry innovations and applications. As an industry leader, Penta continues to pioneer chemistry-based solutions for practically every area of commerce. Our products and expertise have helped fuel technical advances in dozens of commercial applications including flavoring, coloring, fragrances and chemical processes.
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      Product(s):
      13-65350 2-METHYL PIPERIDINE, Kosher
       
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    • TCI AMERICA
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      Product(s):
      P0443 2-Methylpiperidine >98.0%(GC)
       
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2-methylpiperidine (Click)
CAS Number: 109-05-7Picture of molecule
ECHA EINECS - REACH Pre-Reg: 203-642-1
FDA UNII: 22E509663B
Nikkaji Web: J5.086E
Beilstein Number: 0079804
MDL: MFCD00005982
XlogP3-AA: 1.10 (est)
Molecular Weight: 99.17661000
Formula: C6 H13 N
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
EFSA/JECFA Comments: Racemate.
Category: flavoring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist: Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
JECFA Food Flavoring: 1608  2-methylpiperidine
Flavis Number: 14.133 (Old)
DG SANTE Food Flavourings: 14.133  2-methylpiperidine
FEMA Number: 4244  2-methylpiperidine
FDA Mainterm: 2-METHYLPIPERIDINE
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Physical Properties:
Appearance: colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.83800 to 0.84400 @  25.00 °C.
Pounds per Gallon - (est).: 6.973 to  7.023
Refractive Index: 1.44200 to 1.44800 @  20.00 °C.
Boiling Point: 117.00 to  119.00 °C. @ 760.00 mm Hg
Vapor Pressure: 16.395000 mm/Hg @ 25.00 °C. (est)
Flash Point: 50.00 °F. TCC ( 10.00 °C. )
logP (o/w): 1.148 (est)
Soluble in:
 alcohol
 propylene glycol
 water, 5.093e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor Type: ammoniacal
 
Odor Strength: high ,
recommend smelling in a 1.00 % solution or less
 
Substantivity: 2 hour(s) at 1.00 % in propylene glycol
 
 ammoniacal  fishy  seafood  taco  corn chip  
Odor Description:
at 1.00 % in propylene glycol. 
amine fishy seafood taco corn chip
Luebke, William tgsc, (2006)
 
 
Flavor Type: ammoniacal
 
 ammoniacal  creamy  taco  lettuce  
Taste Description:
at 5.00 ppm in water.  
amine creamy taco lettuce
Luebke, William tgsc, (2006)
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
EMD Millipore
For experimental / research use only.
2-Methylpiperidine
Parchem
2-methyl piperidine
Penta International
2-METHYL PIPERIDINE, Kosher
Santa Cruz Biotechnology
For experimental / research use only.
2-Methylpiperidine
Sigma-Aldrich: Aldrich
For experimental / research use only.
2-Methylpiperidine 98%
TCI AMERICA
For experimental / research use only.
2-Methylpiperidine >98.0%(GC)
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Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 11 - Highly flammable.
R 22 - Harmful if swallowed.
R 37/38 - Irritating to respiratory system and skin.
R 41 - Risk of serious damage to eyes.
S 16 - Keep away from sources of ignition - No Smoking.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 39 - Wear eye/face protection.
 
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:
Not determined
Dermal Toxicity:
subcutaneous-rabbit LDLo 300 mg/kg
Berichte der Deutschen Chemischen Gesellschaft. Vol. 34, Pg. 2408, 1901.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: flavoring agents
Recommendation for 2-methyl piperidine usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.012 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.002 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 340 (μg/person/day)
Threshold of Concern:540 (μg/person/day)
Structure Class: II
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 22
Click here to view publication 22
 average usual ppmaverage maximum ppm
baked goods: 2.0000010.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: 0.200001.00000
cheese: 0.400002.00000
chewing gum: --
condiments / relishes: 0.100000.50000
confectionery froastings: 1.000005.00000
egg products: --
fats / oils: 0.100000.50000
fish products: 0.200001.00000
frozen dairy: 0.400002.00000
fruit ices: 0.400002.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 0.200001.00000
milk products: 0.400002.00000
nut products: --
other grains: 0.200001.00000
poultry: 0.200001.00000
processed fruits: 0.400002.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 0.100000.50000
snack foods: 1.000005.00000
soft candy: --
soups: 0.100000.50000
sugar substitutes: --
sweet sauces: --
 
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): 0.100000.50000
Edible ices, including sherbet and sorbet (03.0): 0.400002.00000
Processed fruit (04.1): 0.400002.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 1.000005.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.200001.00000
Bakery wares (07.0): 2.0000010.00000
Meat and meat products, including poultry and game (08.0): 0.200001.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.200001.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.100000.50000
Foodstuffs intended for particular nutritional uses (13.0): 0.200001.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): --
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 1.000005.00000
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
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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):
Flavouring Group Evaluation 86, (FGE.86)[1] - Consideration of aliphatic and aromatic amines and amides evaluated by JECFA (65th meeting) - Scientific Opinion of the Panel on Food Additives - Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 86, Revision 1 (FGE.86Rev1): Consideration of aliphatic and aromatic amines and amides evaluated by JECFA (65th meeting)
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 86, Revision 2 (FGE.86Rev2): Consideration of aliphatic and arylalkyl amines and amides evaluated by JECFA (65th meeting)
View page or View pdf
EPI System: View
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA Substance Registry Services (TSCA): 109-05-7
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 7974
National Institute of Allergy and Infectious Diseases: Data
WISER: UN 1993
WGK Germany: 2
 2-methylpiperidine
Chemidplus: 0000109057
RTECS: TN1240000 for cas# 109-05-7
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References:
 2-methylpiperidine
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 7974
Pubchem (sid): 134973511
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS): View
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB32416
FooDB: FDB009857
Export Tariff Code: 2933.39.9100
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
For Odor
corn chip
 popcorn pyrimidineFL/FR
nutty
2,6-lutidineFL/FR
popcorn
2-acetyl pyrazineFL/FR
sulfurous
 dimethyl sulfideFL/FR
 
For Flavor
 
No flavor group found for these
1-(methyl thio) ethane thiolFL
 prenyl mercaptanFL
 pyridineFL
(R)-N,N,alpha-trimethyl benzyl amineFL
ammoniacal
 pyrrolidineFL
corn chip
2-acetyl-2-thiazolineFL
 popcorn pyrimidineFL/FR
nutty
2,6-lutidineFL/FR
roasted
2-acetyl pyrazineFL/FR
seafood
1,4-dithianeFL
sulfurous
 dimethyl sulfideFL/FR
 
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Potential Uses:
 cereal 
 cheeseFL
 corn chipFL
 fishFL
 seafoodFL
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Occurrence (nature, food, other): note
 beef roasted beef
Search  PMC Picture
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Synonyms:
(±)-2-methyl piperidine
alpha-methyl piperidine
dextro,laevo-2-methyl piperidine
2-methyl-piperidine
(R,S)-2-methylpiperidine
2-methylpiperidine
DL-2-methylpiperidine
(±)-alpha-pipecoline
2-pipecoline
a-pipecoline
alpha-pipecoline
 pipecoline, a
 piperidine, 2-methyl-
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Articles:
Info: aliphatic and aromatic amines and amides derivatives
PubMed: Palladium-catalyzed one-pot three- or four-component coupling of aryl iodides, alkynes, and amines through C-N bond cleavage: efficient synthesis of indole derivatives.
PubMed: An Fmoc compatible, O to S shift-mediated procedure for the preparation of C-terminal thioester peptides.
PubMed: Noncyclam tetraamines inhibit CXC chemokine receptor type 4 and target glioma-initiating cells.
PubMed: Intramolecular aminoalkene hydroamination mediated by a tethered bis(ureate)zirconium complex: computational perusal of various pathways for aminoalkene activation.
PubMed: Mechanistic elucidation of intramolecular aminoalkene hydroamination catalyzed by a tethered bis(ureate) complex: evidence for proton-assisted C-N bond formation at zirconium.
PubMed: [Regioselectivity in the dehydrogenation of substituted ethylenediamines as nicotine models].
PubMed: Analysis of vibrational spectra of 2 and 3-methylpiperidine based on density functional theory calculations.
PubMed: [Seperation and structure elucidation of alkaloids from Chinese drug buzhaye, Folium Microcos].
PubMed: Efficient solid-phase synthesis of sulfotyrosine peptides using a sulfate protecting-group strategy.
PubMed: Oviposition deterrence and larvicidal activity of three formulations of piperidine repellent (AI3-37220) against field populations of Stegomyia albopicta.
PubMed: Three dimensional structure-activity relationships (3D-QSAR) for insect repellency of diastereoisomeric compounds: a hierarchical molecular overlay approach.
PubMed: Mechanism of hydrodenitrogenation on phosphides and sulfides.
PubMed: Normal-phase chiral liquid chromatography-mass spectrometry of non-UV-active compounds: applications for pharmaceutically relevant racemates.
PubMed: Direct chemical synthesis of chiral methanol of 98% ee and its conversion to [(2)H1,(3)H]methyl tosylate and [(2)H1,(3)H-methyl]methionine.
PubMed: Preparation, cytotoxicity and interactions with nucleophiles of three isomeric transplatinum complexes containing methylpiperidine ligands.
PubMed: Optically active arthropod repellents for use against disease vectors.
PubMed: A new module for quantitative evaluation of repellent efficacy using human subjects.
PubMed: Synthesis and repellent efficacy of a new chiral piperidine analog: comparison with Deet and Bayrepel activity in human-volunteer laboratory assays against Aedes aegypti and Anopheles stephensi.
PubMed: Release of nitric oxide from novel diazeniumdiolates monitored by laser magnetic resonance spectroscopy.
PubMed: Stereochemical effects in an insect repellent.
PubMed: Field evaluation of repellents containing deet and AI3-37220 against Anopheles koliensis in Papua New Guinea.
PubMed: Field evaluation of deet and a piperidine repellent against Aedes communis (Diptera: Culicidae) and Simulium venustum (Diptera: Simuliidae) in the Adirondack Mountains of New York.
PubMed: Laboratory evaluation of AI3-37220, AI3-35765, CIC-4, and deet repellents against three species of mosquitoes.
PubMed: Field evaluation of the repellents deet, CIC-4, and AI3-37220 against Anopheles in Lae, Papua New Guinea.
PubMed: Short report: prevention of Schistosoma mansoni infections in mice by the insect repellents AI3-37220 and N,N-diethyl-3-methylbenzamide.
PubMed: Laboratory and field evaluation of the repellents deet, CIC-4, and AI3-37220 against Anopheles farauti (Diptera: Culicidae) in Australia.
PubMed: Increase of mucous glycoprotein secretion by tumor necrosis factor alpha via a protein kinase C-dependent mechanism in cultured chinchilla middle ear epithelial cells.
PubMed: Laboratory and field evaluation of deet, CIC-4, and AI3-37220 against Anopheles dirus (Diptera: Culicidae) in Thailand.
PubMed: Field evaluation of arthropod repellents, deet and a piperidine compound, AI3-37220, against Anopheles funestus and Anopheles arabiensis in western Kenya.
PubMed: Laboratory tests of arthropod repellents against Leptotrombidium deliense--noninfected and infected with Rickettsia tsutsugamushi--and noninfected L. fletcheri (Acari: Trombiculidae).
PubMed: Laboratory and field evaluation of five repellents against the black flies Prosimulium mixtum and P. fuscum (Diptera: Simuliidae).
PubMed: Opioid and nicotinic medullary hyperalgesic influences in the decerebrated rat.
PubMed: Interactions of piperidine derivatives with the nicotinic cholinergic receptor complex from Torpedo electric organ.
PubMed: Effects of the protein kinase C inhibitor H-7 and calmodulin antagonist W-7 on superoxide production in growing and resting human histiocytic leukemia cells (U937).
PubMed: Fourth ventricle effects of nicotine, 2-methylpiperidine and cytisine in dogs.
PubMed: Stereospecificity of 2-methylpiperidine binding to a nicotinic up-regulatory site in the rat brain P2 preparation.
PubMed: Structure-activity relationships of some pyridine, piperidine, and pyrrolidine analogues for enhancing and inhibiting the binding of (+/-)-[3H]nicotine to the rat brain P2 preparation.
PubMed: Studies on pyrazine derivatives. Part X. Synthesis and tuberculostatic activity of some 6-cyclamino-, 6-imidazolyl--and triazolylpyrazine-2-carboxylic acids derivatives.
PubMed: [Synthesis of N-(beta-ethoxyethyl)-2-methylpiperidine].
PubMed: The use of 2-pipecoline in the Mannich reaction.
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