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2-ethyl-5-methyl thiophene
2-ethyl-5-methyl thiophene is a heterocyclic sulfur compound used as a flavoring agent known for its sulfurous and green sensory properties.
General Material Description
2-ethyl-5-methyl thiophene is a sulfur-containing heterocyclic organic compound with molecular formula C7H10S. It appears as a clear liquid characterized by a distinct sulfurous odor combined with green, leafy, and phenolic flavor notes. This compound belongs to the thiophene chemical group, which consists of a five-membered ring containing sulfur. It is also known by several synonyms, including 2-ethyl-5-methylthiophene and 5-methyl-2-ethylthiophene. Its chemical and physical data are recorded in comprehensive public databases such as PubChem. The compound is typically synthesized for use as a flavoring agent and occurs naturally in trace amounts in certain roasted meats, contributing to their characteristic aroma profiles.
Occurrence, Applicability & Potential Uses
2-ethyl-5-methyl thiophene occurs naturally in trace concentrations in grilled or roasted pork, where it contributes subtle sulfurous and green notes to the complex aroma profile of cooked meat. Its presence in food is recognized in flavor science for adding depth and authenticity to meat flavorings. The compound is primarily applied as a flavoring agent in various food products, providing characteristic sulfurous and leafy green flavors. Regulatory standards, such as those from FEMA (US), catalogue it within acceptable flavoring substances, permitting controlled use in food categories including dairy products, fats and oils, confectionery, beverages, and processed meats, among others. These use levels are governed to ensure sensory impact while maintaining consumer safety.
Physico-Chemical Properties Summary
2-ethyl-5-methyl thiophene is a low molecular weight organic liquid with a molecular weight around 126.2 g/mol. It exhibits moderate volatility, with a boiling point between 160 and 161 °C at standard atmospheric pressure. The substance has a specific gravity near 0.97 at 25 °C and a refractive index range from 1.503 to 1.509 at 20 °C. Its vapor pressure at 25 °C is approximately 3.17 mmHg, indicating moderate evaporation potential at room temperature. It is soluble in alcohol and exhibits limited water solubility estimated at about 119 mg/L at 25 °C. The estimated log P value of 3.35 suggests moderate lipophilicity, influencing its behavior in flavor formulations and partitioning in mixtures. The compound’s flash point is 31 °C (converted from 88 °F), denoting a relatively low ignition temperature valuable for handling and safety considerations.
FAQ
What is 2-ethyl-5-methyl thiophene and what are its main characteristics?
2-ethyl-5-methyl thiophene is an organic sulfur-containing heterocyclic compound belonging to the thiophene family. It features a five-membered aromatic ring with sulfur and substituents ethyl and methyl attached at specific positions. The compound is recognized for its distinct sulfurous odor combined with green and leafy flavor notes. It is mainly used as a flavoring agent to impart characteristic sensory qualities, especially in food products resembling roasted or grilled meat aromas.
Where is 2-ethyl-5-methyl thiophene found and how is it typically used?
This compound occurs naturally in trace amounts in grilled and roasted pork, contributing to the meat's aromatic complexity. It is utilized primarily as a flavoring agent in various food products to reproduce or enhance sulfurous and green notes associated with cooked meats and savory items. Its application covers several food categories, including dairy products, fats and oils, confectionery, beverages, and processed meats, with controlled usage limits defined by regulatory authorities to maintain safety and sensory effectiveness.
What regulations and safety data apply to 2-ethyl-5-methyl thiophene in food use?
2-ethyl-5-methyl thiophene is reviewed and permitted as a flavoring substance under FEMA (US) guidelines and evaluated within Commission Regulation EC No. 1565/2000 in the European Union. Its usage levels vary across food categories with specified maximum concentrations to ensure consumer safety. Toxicological assessments report no significant hazard classifications under OSHA standards. Flavor industry data suggest usage should be restricted to flavor applications and not for fragrance purposes. Safety information is available through EFSA scientific opinions and other authoritative toxicology databases.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 2-ethyl-5-methylthiophene | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 520990 |
| Pubchem (sid): | 10521777 |
| Publications by US Patents | |
| 3,931,166 - Certain 2,5-dimethyl-3-thiopyrazines | |
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 |
| HMDB (The Human Metabolome Database): | HMDB29733 |
| FooDB: | FDB000929 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2-ethyl-5-methyl thiophene |
| Trivial Name | 2-Ethyl-5-methylthiophene |
| Short Description | thiophene, 2-ethyl-5-methyl- |
| Formula | C7 H10 S |
| CAS Number | 40323-88-4 |
| FDA UNII | Search |
| MDL | MFCD00053128 |
| xLogP3-AA | 2.80 (est) |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| BOC Sciences | Endeavour Specialty Chemicals |
| Matrix Scientific | R C Treatt & Co Ltd |
| Robinson Brothers | Santa Cruz Biotechnology |
| Synerzine |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 126.22170257568 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.013 to 8.071 |
| Refractive Index | 1.503 to 1.509 @ 20 °C |
| Boiling Point | 160 to 161°C @ 760 mm Hg |
| Vapor Pressure | 3.166 mmHg @ 25 °C |
| Flash Point TCC Value | 31.11 °C TCC |
| logP (o/w) | 3.348 est |
| Solubility | |
| alcohol | Yes |
| water, 119 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Sulfurous | |
| sulfurous, ethereal, solvent, fruity, burnt | |
| General comment | At 0.10 % in propylene glycol. sulfurous ethereal solvent fruity burnt |
| Flavor Type: Green | |
| green, oily, leafy, geranium, phenolic | |
| General comment | Green oily leafy geranium phenolic |
Occurrences
| (data available) |
Safety Information
Safety information
| 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: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 2-ethyl-5-methyl thiophene usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.061 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 78 (μg/person/day) | ||
| Threshold of Concern: | 540 (μg/person/day) | ||
| Structure Class: | II | ||
| 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/kg | maximum usage mg/kg | ||
| Dairy products, excluding products of category 02.0 (01.0): | 0.20000 | 1.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.10000 | 0.50000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.20000 | 1.00000 | |
| Processed fruit (04.1): | 0.20000 | 1.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 0.20000 | 1.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 0.10000 | 0.50000 | |
| Bakery wares (07.0): | 0.20000 | 1.00000 | |
| Meat and meat products, including poultry and game (08.0): | 0.10000 | 0.20000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.10000 | 0.20000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.10000 | 0.50000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 0.20000 | 1.00000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 0.10000 | 0.50000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 0.20000 | 1.00000 | |
| Ready-to-eat savouries (15.0): | 0.40000 | 2.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.10000 | 0.50000 | |
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 21: Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29. Miscellaneous substances from chemical group 30. (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 76, (FGE.76)[1] - Consideration of sulphur-containing heterocyclic compounds evaluated by JECFA (59th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29, miscellaneous substances from chemical group 30 evaluated by EFSA in FGE.21 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Flavouring Group Evaluation 21, Revision 1 (FGE.21Rev1): Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29 Miscellaneous substances from chemical group 30 View page or View pdf |
| Flavouring Group Evaluation 93 (FGE.93): Consideration of sulphur heterocyclic evaluated by JECFA (68th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl evaluated by EFSA in FGE.21Rev1 (2009) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 21, Revision 2 (FGE.21Rev2): Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29. Miscellaneous substances from chemical group 30. View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 21, Revision 3 (FGE.21Rev3): Thiazoles, thiophenes, thiazoline and thienyl derivatives from chemical groups 29 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 21, Revision 4 (FGE.21Rev4): Thiazoles, thiophenes, thiazoline and thienyl derivatives from chemical groups 29 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 21, Revision 5 (FGE.21Rev5): Thiazoles, thiophenes, thiazoline and thienyl derivatives from chemical groups 29 and 30 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :520990 |
| National Institute of Allergy and Infectious Diseases:Data |
| 2-ethyl-5-methylthiophene |