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methyl thioacetate
Methyl thioacetate is a sulfurous organosulfur compound used as a flavoring agent, known for its eggy, cheese-like odor and presence in foods like coffee and meat.
General Material Description
Methyl thioacetate is an organosulfur compound with the molecular formula C3H6OS. This volatile ester exhibits a characteristic sulfurous and egg-like odor profile reminiscent of cheeses and cooked vegetables. Known also as S-methyl ethanethioate among various synonyms, it appears as a colorless liquid under standard conditions. Extensively documented in the PubChem database (CID 73750), methyl thioacetate is naturally found in diverse foods including coffee, beer, and various fruits. It can be isolated from biological sources or synthesized for use as a flavoring agent, especially to enhance meat and coffee notes. The compound's sulfurous sensory attributes are key to its flavor applications, while its solubility and volatility support its inclusion in complex aroma formulations.
Occurrence, Applicability & Potential Uses
Methyl thioacetate naturally occurs in many food items such as boiled beef, beer, coffee, fish oil, melon, onion, pineapple, pork liver, wild strawberries, whiskey, and wine. It contributes to the sulfurous notes characteristic of cooked and fermented products. Its application primarily lies in flavoring meat and coffee products where a roasted or overripe sulfurous accent is desired. Flavor regulatory frameworks such as FEMA (US) recognize methyl thioacetate under number 3876, supporting its safe use within defined concentration limits. The compound's role as a flavoring agent takes advantage of its distinctive odor profile to enhance the sensory complexity of diverse edible goods.
Physico-Chemical Properties Summary
Methyl thioacetate is a moderately volatile ester with a boiling point between 95 and 96°C at standard atmospheric pressure. It has a specific gravity ranging from 0.817 to 0.825 at 25°C and a refractive index between 1.46 and 1.468 at 20°C. The compound shows full solubility in alcohols, oils, and water at approximately 80 mg/L at 25°C, facilitating blend formulations with various solvents. Its estimated octanol-water partition coefficient (logP) is about 0.859, indicating balanced hydrophilicity suitable for flavor dispersion. With a flash point near 53°C, methyl thioacetate requires handling precautions to avoid ignition. These physicochemical attributes influence its stability and release in flavor applications.
FAQ
What is methyl thioacetate and what are its key characteristics?
Methyl thioacetate is an organosulfur compound known for its characteristic sulfurous and egg-like odor, often described as reminiscent of cheese, cabbage, and cooked vegetables. This volatile ester is used as a flavoring agent due to its distinctive aroma profile. It is chemically represented by the formula C3H6OS and occurs naturally in various foods including coffee, beer, and meats. Synonyms include S-methyl ethanethioate and S-methyl thioacetate. Its distinctive odor derives from the sulfur-containing functional group, which plays a significant role in its sensory properties.
Where is methyl thioacetate found naturally and how is it used commercially?
Methyl thioacetate is naturally present in numerous food products such as boiled beef, fish oil, onion, pineapple, wild strawberry, whiskey, and wine. Its sulfurous notes contribute to the flavor complexity of these items. Commercially, it is utilized primarily as a flavoring agent in coffee and meat products to impart roasted, overripe, or sulfurous sensory qualities. The compound's compatibility with solvents like alcohol and oils enhances its incorporation into flavor formulations. Regulatory bodies like FEMA (US) acknowledge its safe flavor use under regulated concentration limits.
What safety and regulatory guidelines apply to methyl thioacetate in flavoring applications?
Methyl thioacetate is classified as an irritant with the European Union hazard codes indicating it is highly flammable and may irritate skin, eyes, and respiratory systems. It requires appropriate handling, including use of protective equipment and avoidance of ignition sources. Regulatory reviews by FEMA (US) deem it generally recognized as safe (GRAS) for flavoring within specified concentration ranges in foods such as baked goods, beverages, and meat products. Additionally, EFSA (European Food Safety Authority) has conducted comprehensive evaluations confirming its suitability within regulated limits. Usage beyond flavor applications is not recommended. Safety data sheets provide detailed precautions for storage and handling.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| S-methyl ethanethioate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 1534-08-3 |
| Pubchem (cid): | 73750 |
| Pubchem (sid): | 135032326 |
| Pherobase: | View |
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 |
| HMDB (The Human Metabolome Database): | HMDB31189 |
| FooDB: | FDB003209 |
| Export Tariff Code: | 2930.90.9190 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | S-Methyl thioacetate |
General Material Information
| Preferred name | methyl thioacetate |
| Trivial Name | S-Methyl thioacetate |
| Short Description | S-methyl acetothioate |
| Formula | C3 H6 O S |
| CAS Number | 1534-08-3 |
| FEMA Number | 3876 |
| Flavis Number | 12.149 |
| ECHA Number | 216-252-1 |
| FDA UNII | PF2D4MWX79 |
| Nikkaji Number | J125.731E |
| MDL | MFCD00014989 |
| xLogP3-AA | 0.70 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 482 S-methyl thioacetate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 1534-08-3 ; S-METHYL THIOACETATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 90.14501953125 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 6.798 to 6.865 |
| Refractive Index | 1.46 to 1.468 @ 20 °C |
| Boiling Point | 95 to 96°C @ 760 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 57.889999 mmHg @ 25 °C |
| Flash Point TCC Value | 11.67 °C TCC |
| logP (o/w) | 0.859 est |
| Solubility | |
| alcohol | Yes |
| oils | Yes |
| water, 8.012e+004 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Sulfurous | |
| sulfurous, eggy, cheesy, dairy, vegetable, cabbage | |
| General comment | At 0.10 % in propylene glycol. sulfurous eggy cheese dairy vegetable cabbage |
| Flavor Type: Sulfurous | |
| sulfurous, fruit overripe fruit, roasted, cheesy, gassy, vegetable | |
| General comment | Sulfurous overripe rotten roasted |
Occurrences
| (data available) |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 11 - Highly flammable. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. 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. | |
| 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 methyl thioacetate usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | ND (μg/capita/day) | ||
| Structure Class: | I | ||
| 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: 18 | |||
| Click here to view publication 18 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.10000 | 5.00000 | |
| beverages(nonalcoholic): | 0.10000 | 5.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | 0.10000 | 5.00000 | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 0.10000 | 5.00000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | 0.10000 | 5.00000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 0.10000 | 5.00000 | |
| milk products: | 0.10000 | 5.00000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 100.00000 | 1000.00000 | |
| snack foods: | - | - | |
| soft candy: | 0.10000 | 5.00000 | |
| soups: | 0.10000 | 5.00000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | 0.10000 | 5.00000 | |
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): |
| Flavouring Group Evaluation 8 (FGE.08)[1]: Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical group 20 View page or View pdf |
| Flavouring Group Evaluation 8, Revision 1 (FGE.08Rev1): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 8, Revision 3 (FGE.08Rev3): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 08, Revision 4 (FGE.08Rev4): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 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 :73750 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 1993 |
| WGK Germany:3 |
| S-methyl ethanethioate |
| Chemidplus:0001534083 |