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2-methyl 3-(methyl thio) furan
2-methyl 3-(methyl thio) furan is a sulfur-containing furan compound used as a flavoring agent with meaty, spicy notes found in cooked beef and coffee.
General Material Description
2-methyl 3-(methyl thio) furan is a sulfur-containing heterocyclic organic compound classified as a substituted furan. It is visually a clear to pale liquid with a molecular formula of C6H8OS and a molecular weight of approximately 128.19 g/mol. This compound has notable organoleptic characteristics, including sulfurous, meaty, and spicy aroma notes, often described as having nuances reminiscent of beef, coffee, and cheese. Common synonyms include dimethyl thiofurane and 2-methyl-3-methylsulfanylfuran. It is referenced in controlled-vocabulary chemical databases such as PubChem CID 526618. The compound is typically obtained from natural occurrences in foods or via synthetic routes for use in flavor formulations.
Occurrence, Applicability & Potential Uses
2-methyl 3-(methyl thio) furan naturally occurs in various cooked foods, prominently in cooked beef, coffee, and tea, contributing to their characteristic aroma profiles. Its flavor profile is predominantly sulfurous and meaty, making it valuable in flavoring applications that aim to replicate or enhance cooked meat, chocolate, cocoa, nutty, and wasabi-like notes. The compound is recognized by regulatory bodies such as FEMA (US), where it is listed under number 3949, and JECFA (FAO/WHO), under evaluation number 1061, confirming its acceptance for use as a flavoring agent. Usage levels are controlled to ensure sensory effectiveness while maintaining safety.
Physico-Chemical Properties Summary
Physicochemically, 2-methyl 3-(methyl thio) furan is a moderately volatile compound with an estimated logP of 2.324, indicating moderate lipophilicity. Its specific gravity ranges from 1.064 to 1.071 at 20 °C, and the refractive index varies between 1.506 and 1.514 at the same temperature. The vapor pressure is 2.606 mmHg at 25 °C, consistent with its volatility suitable for aroma applications. Solubility data indicate it is soluble in alcohol and moderately soluble in water (approximately 670.5 mg/L at 25 °C). The flash point is around 37.8 °C (100 °F), highlighting the need for careful handling under elevated temperatures. These properties influence its behavior in formulations and its sensory release profile.
FAQ
What is 2-methyl 3-(methyl thio) furan and where does it come from?
2-methyl 3-(methyl thio) furan is a sulfur-substituted furan compound known for its role as a flavoring agent. It naturally occurs in cooked beef, coffee, and tea, contributing significantly to their characteristic meaty and sulfurous aroma profiles. This compound can also be synthesized for use in flavor formulations that aim to reproduce these sensory attributes.
How is 2-methyl 3-(methyl thio) furan used in food flavoring?
This compound is utilized primarily as a flavoring agent to impart meaty, spicy, and sulfurous notes in food products. Its applications include enhancing flavors in baked goods, meat products, seasonings, and beverages like coffee and cocoa. Usage levels vary depending on the food matrix but are kept within the regulatory limits to maintain sensory quality without overpowering or safety risks.
What regulations govern the use and safety of 2-methyl 3-(methyl thio) furan?
2-methyl 3-(methyl thio) furan is regulated under FEMA (US) with FEMA number 3949 and evaluated by JECFA (FAO/WHO) as flavoring agent number 1061. Safety assessments include usage limits in various food categories, no observed effect levels, and exposure estimates such as maximized survey-derived daily intakes (MSDI). It is classified as a structure class II compound for safety evaluations, and its use levels are guided to ensure consumer safety without specific hazard labelling in global food safety frameworks.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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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 |
| HMDB (The Human Metabolome Database): | HMDB36610 |
| FooDB: | FDB015526 |
| YMDB (Yeast Metabolome Database): | YMDB01452 |
| Export Tariff Code: | 2930.90.9999 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| EFSA Update of results on the monitoring of furan levels in food: | Read Report |
| EFSA Previous report: Results on the monitoring of furan levels in food: | Read Report |
| EFSA Report of the CONTAM Panel on provisional findings on furan in food: | Read Report |
General Material Information
| Preferred name | 2-methyl 3-(methyl thio) furan |
| Trivial Name | 2-Methyl-3-(methylthio)furan |
| Short Description | 2-methyl-3-(methylthio)furan |
| Formula | C6 H8 O S |
| CAS Number | 63012-97-5 |
| FEMA Number | 3949 |
| Flavis Number | 13.152 |
| FDA UNII | M46N02LDL4 |
| Nikkaji Number | J641.813I |
| MDL | MFCD03701635 |
| xLogP3-AA | 1.90 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1061 2-methyl-3-(methylthio)furan |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 63012-97-5 ; 2-METHYL-3-(METHYLTHIO)FURAN |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 128.19395446777 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.864 to 8.922 |
| Refractive Index | 1.506 to 1.514 @ 20 °C |
| Vapor Pressure | 2.606 mmHg @ 25 °C |
| Flash Point TCC Value | 37.78 °C TCC |
| logP (o/w) | 2.324 est |
| Solubility | |
| alcohol | Yes |
| water, 670.5 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Sulfurous | |
| beefy, cheesy, coffee, minty, spicy, pungent, alliaceous, sulfurous, dry, meaty, brothy, mustard | |
| General comment | At 10.00 % in triacetin. beefy cheese coffee minty spicy |
| Mosciano, Gerard P&F 26, No. 5, 68, (2001) | At 1.00 % in propylene glycol. Spicy, pungent alliaceous, sulfurous drying to a meaty brothy aroma with mustard and coffee nuances |
| Flavor Type: Meaty | |
| meaty, spicy, solvent, coffee, nutty, cheesy | |
| Mosciano, Gerard P&F 26, No. 5, 68, (2001) | At 0.10 - 0.40 ppm. Mild meaty, spicy, slightly solvent like with coffee, nutty and cheesy nuances |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Flavoring purposes | Chocolate cocoa , Coffee , Meat , Nut , Wasabi |
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: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 2-methyl 3-(methyl thio) furan usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1.20 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.10 (μg/capita/day) | ||
| NOEL (No Observed Effect Level): | 1.30 (mg/kg bw per 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: 19 | |||
| Click here to view publication 19 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.02000 | 0.20000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | 0.00500 | 0.05000 | |
| chewing gum: | - | - | |
| condiments / relishes: | 0.00100 | 0.01000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | 0.03000 | 0.30000 | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | 0.03000 | 0.30000 | |
| hard candy: | - | - | |
| imitation dairy: | 0.00500 | 0.05000 | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 0.05000 | 0.50000 | |
| milk products: | 0.00500 | 0.05000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | 0.05000 | 0.50000 | |
| processed fruits: | - | - | |
| processed vegetables: | 0.00300 | 0.03000 | |
| reconstituted vegetables: | 0.00300 | 0.03000 | |
| seasonings / flavors: | 0.05000 | 0.50000 | |
| snack foods: | 0.03000 | 0.30000 | |
| soft candy: | - | - | |
| soups: | 0.03000 | 0.30000 | |
| 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 13 (FGE.13); Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 (Commission Regulation (EC) No 1565/2000 of 18 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 13Rev1: Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 View page or View pdf |
| Consideration of sulfur-substituted furan derivatives used as flavouring agents evaluated by JECFA (59th meeting) structurally related to a subgroup of substances within the group of Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 evaluated by EFSA in FGE.13Rev1 (2009) View page or View pdf |
| Flavouring Group Evaluation 67 (FGE.67): Consideration of 40 furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by JECFA at the 65th meeting (JECFA, 2006b) and re-evaluated at the 69th meeting (JECFA, 2009c) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 13, Revision 2 (FGE.13Rev2): Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 67, Revision 1 (FGE.67Rev.1): Consideration of 40 furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by JECFA at the 65th meeting (JECFA, 2006b) and re-evaluated at the 69th meeting (JECFA, 2009c) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 65, Revision 1 (FGE.65Rev1): Consideration of sulfur-substituted furan derivatives used as flavouring agents evaluated by JECFA (59th meeting) structurally related to a subgroup of substances within the group of Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 evaluated by EFSA in FGE.13Rev2 (2011) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 13 Revision 3 (FGE.13Rev3): furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 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 :526618 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 1993 |
| WGK Germany:3 |
| 2-methyl-3-methylsulfanylfuran |
| Chemidplus:0063012975 |