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5-ethyl-2-methyl pyridine
5-ethyl-2-methyl pyridine is a heterocyclic aromatic compound used primarily as a flavoring agent, exhibiting nutty and winey sensory characteristics.
General Material Description
5-ethyl-2-methyl pyridine is a heterocyclic aromatic compound belonging to the pyridine family, characterized by a molecular formula of C8H11N and a molecular weight of approximately 121.18 g/mol. It appears as a clear liquid with notable odor and flavor attributes described as nutty and winey, contributing to its use as a flavoring agent in food products. The compound is known under various synonyms including 5-ethyl-2-picoline and 2,5-aldehydine. It is chemically related to methyl and ethyl-substituted pyridines and is cataloged in chemical databases such as PubChem. This compound can be sourced both from natural occurrences in foods like red beans, cheese, and peppermint leaves, and through synthetic processes for flavor industry applications.
Occurrence, Applicability & Potential Uses
5-ethyl-2-methyl pyridine naturally occurs in various foods including red beans, cheese, fried chicken, eggs, lamb fat, peppermint leaf, and tea leaf. Its presence contributes to distinctive aroma profiles encountered in these items. Due to its sensory properties—nutty, earthy odor and winey flavor—it is utilized as a flavoring agent to impart mushroom, nut, and potato notes, complementing complex flavor formulations in the food industry. The compound's use complies with relevant regulatory frameworks such as FEMA (US) standards, notably FEMA number 3546, ensuring its safety and acceptability as a flavor substance. Additionally, its inclusion in JECFA evaluations by the FAO/WHO supports controlled usage levels in food products.
Physico-Chemical Properties Summary
5-ethyl-2-methyl pyridine exhibits physical properties relevant to formulation and handling. It has a boiling point ranging from 172 to 175°C at standard atmospheric pressure and a specific gravity between 0.917 and 0.923 at 25°C. The compound shows moderate vapor density (approximately 4.2 times air) and exhibits a log P (octanol-water partition coefficient) estimated at 2.178, indicating moderate lipophilicity. Its refractive index varies from 1.495 to 1.502 at 20°C. Solubility is limited in water (about 12,000 mg/L at 20°C) but it dissolves readily in alcohol solvents. The flash point is approximately 151°F (66°C), signaling the temperature at which it forms ignitable vapor-air mixtures. These properties influence its formulation in flavor blends and safety handling measures.
FAQ
What is 5-ethyl-2-methyl pyridine and what are its main uses?
5-ethyl-2-methyl pyridine is a substituted pyridine derivative used primarily as a flavoring agent in the food industry. It provides sensory notes described as nutty and winey, contributing mushroom, nut, and potato-like flavors to various food products. This compound is found naturally in foods such as red beans, cheese, and peppermint leaf but is also synthetically produced to achieve consistency in flavor applications.
In which natural sources is 5-ethyl-2-methyl pyridine found, and how is it applied industrially?
This compound occurs naturally in several foods including red beans, cheese, fried chicken, eggs, lamb fat, peppermint leaf, and tea leaf, where it contributes to their characteristic aroma profiles. Industrially, it is incorporated into flavor formulations to enhance and modify flavor profiles, commonly within baked goods, snack foods, gravies, and processed meat products. The compound's compatibility with alcohol solvents and moderate water solubility facilitate its use in diverse formulations.
What regulations apply to the use of 5-ethyl-2-methyl pyridine in food flavoring and how is safety assessed?
5-ethyl-2-methyl pyridine is regulated under standards such as FEMA (US), where it holds FEMA number 3546, and has been evaluated by JECFA, confirming its acceptable use as a flavoring agent within defined limits. Safety information indicates it has low acute toxicity at typical exposure levels but requires standard precautions during handling. Regulatory bodies mandate exposure limits and assess toxicological data to ensure consumer safety. Usage levels are controlled, and the compound is not recommended for fragrance applications.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 5-ethyl-2-methylpyridine | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 104-90-5 |
| Pubchem (cid): | 7728 |
| Pubchem (sid): | 134970832 |
| Publications by US Patents | |
| 3,931,166 - Certain 2,5-dimethyl-3-thiopyrazines | |
| Flavoring agent | |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB29729 |
| FooDB: | FDB000925 |
| Export Tariff Code: | 2933.39.9100 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Formulations/Preparations: •grade: technical •grades or purity: 99.9% | |
General Material Information
| Preferred name | 5-ethyl-2-methyl pyridine |
| Trivial Name | 5-Ethyl-2-methylpyridine |
| Short Description | 5-ethyl-2-methylpyridine |
| Formula | C8 H11 N |
| CAS Number | 104-90-5 |
| FEMA Number | 3546 |
| Flavis Number | 14.066 |
| ECHA Number | 203-250-0 |
| FDA UNII | WG205CGK3Y |
| Nikkaji Number | J5.037G |
| Beilstein Number | 0109269 |
| MDL | MFCD00006344 |
| COE Number | 11385 |
| xLogP3-AA | 2.00 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1318 5-ethyl-2-methylpyridine |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 104-90-5 ; 5-ETHYL-2-METHYLPYRIDINE |
| Synonyms |
|
Suppliers
| Beijing Lys Chemicals | EMD Millipore |
| Parchem | Penta International |
| R C Treatt & Co Ltd | Santa Cruz Biotechnology |
| Sigma-Aldrich | Synerzine |
| TCI AMERICA | Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 121.18267059326 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.63 to 7.68 |
| Refractive Index | 1.495 to 1.502 @ 20 °C |
| Boiling Point | 172 to 175°C @ 760 mm Hg |
| Vapor Pressure | 1.43 mmHg @ 25 °C |
| Vapor Density | 4.2 |
| Flash Point TCC Value | 66.11 °C TCC |
| logP (o/w) | 2.178 est |
| Solubility | |
| alcohol | Yes |
| water, 12000 mg/L @ 20 °C (exp) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Nutty | |
| nutty, potato raw potato, roasted, earthy | |
| General comment | At 0.10 % in propylene glycol. nutty strong raw potato roasted earthy |
| Flavor Type: Winey | |
| winey, buttery, acidic, cereal, sulfurous, solvent | |
| General comment | Winey buttery acidic cereal sulfurous solvent |
Occurrences
| (data available) |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 20/22 - Harmful by inhalation and if swallowed. R 52/53 - Harmful to qauatic organisms, may cause long-term adverse effects in the aquatic environment. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. S 23 - Do not breath vapour. 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 36/37/39 - Wear suitable clothing, gloves and eye/face protection. S 45 - In case of accident or if you feel unwell seek medical advice immediately. S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet. | |
| 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 1540 mg/kg (Smyth et al., 1951a) oral-rat LD50 368 mg/kg (Izmerov et al., 1982) oral-mouse LD50 282 mg/kg (Izmerov et al., 1982) oral-mouse LD50 282 mg/kg "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 83, 1982. oral-rat LD50 1300 uL/kg LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) National Technical Information Service. Vol. OTS0571695 | |
| Dermal Toxicity: | |
| skin-rabbit LD50 566 ul/kg LIVER: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA National Technical Information Service. Vol. OTS0571695 subcutaneous-rat LD50 826 mg/kg "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 83, 1982. subcutaneous-mouse LD50 294 mg/kg "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 83, 1982. skin-guinea pig LD50 2500 mg/kg "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 846, 1986. | |
| Inhalation Toxicity: | |
| inhalation-rat LC50 540 ppm/4H BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA National Technical Information Service. Vol. OTS0571695 | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 5-ethyl-2-methyl pyridine usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.12 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.04 (μg/capita/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: 11 | |||
| Click here to view publication 11 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 1.50000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | 1.00000 | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 0.50000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | 0.05000 | |
| jams / jellies: | - | - | |
| meat products: | - | 1.00000 | |
| milk products: | - | - | |
| nut products: | - | 1.00000 | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | 0.50000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
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 77, Revision 2 (FGE.77Rev2): 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.24Rev2 (2013) View page or View pdf |
| Scientific opinion on flavouring group evaluation 77, revision 3 (FGE.77Rev3): 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.24Rev2 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA GENetic TOXicology:Search |
| EPA Substance Registry Services (TSCA):104-90-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :7728 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 2300 |
| WGK Germany:1 |
| 5-ethyl-2-methylpyridine |
| Chemidplus:0000104905 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:TJ6825000 for cas# 104-90-5 |