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ethyl methyl mercaptopropionate
Ethyl methyl mercaptopropionate is a sulfurous ester used in flavor and fragrance applications, notable for its pineapple-like fruity aroma and presence in various fruits and beverages.
General Material Description
Ethyl methyl mercaptopropionate is an organosulfur compound classified as an ester with the molecular formula C6H12O2S. It appears as a clear liquid with a characteristic sulfurous odor reminiscent of pineapple, tropical fruits, and ripe tomatoes. Known also as ethyl 3-methylthiopropionate and by numerous synonyms, it contributes distinctive fruity and sulfur-containing notes to flavors and fragrances. This compound occurs naturally in various fruits and beverages and can be sourced synthetically for use in food flavorings and perfumery. Detailed chemical information is cataloged in the ChEBI database. It is employed primarily as a flavor and fragrance agent with applications spanning bakery products, beverages, and confectionery.
Occurrence, Applicability & Potential Uses
Ethyl methyl mercaptopropionate occurs naturally in multiple foodstuffs including beer, brandy, Parmesan cheese, kiwi, passion fruit juice, pineapple, malt whiskey, and white wine. Its biological occurrence in these foods imparts characteristic sulfurous and fruity aroma notes. Applied commercially, it functions as a flavoring agent enhancing tropical fruit, pineapple, citrus, and tomato profiles within bakery, beverage, cheese, and confectionery products. Regulatory frameworks such as FEMA (US) provide guidance on safe usage levels in these applications. Its contribution to flavor complexity and aromatic profiles makes it valuable in formulations requiring sulfurous and fruity nuances, particularly in soft confectionery and tropical fruit flavors.
Physico-Chemical Properties Summary
Ethyl methyl mercaptopropionate is a moderately volatile ester with a boiling point near 196 to 197 °C at standard pressure, indicative of reasonable stability under typical processing conditions. Its specific gravity ranges from 1.03 to 1.035 at 25 °C, and its refractive index varies between 1.457 and 1.463 at 20 °C, reflecting its liquid density and optical properties. With a vapor density of 5.1 relative to air and a vapor pressure of 0.324 mm Hg at 25 °C, it displays moderate volatility relevant to aroma release. The estimated logP of approximately 1.35 suggests balanced hydrophobicity affecting its partitioning in formulations. It is soluble in alcohol and moderately soluble in water (estimated 4534 mg/L at 25 °C), but not fully miscible, so solvent choice affects formulation compatibility. Storage requires protection from heat and light to maintain shelf life beyond 24 months. These characteristics influence its behavior in flavor and fragrance matrices.
FAQ
What is ethyl methyl mercaptopropionate and what are its key sensory attributes?
Ethyl methyl mercaptopropionate is an organosulfur ester known chemically as ethyl 3-methylthiopropionate. It has a distinctive sulfurous odor and flavor profile that includes notes of pineapple, tropical fruit, ripe tomato, and subtle metallic or sulfury nuances. These sensory properties make it valuable as a flavor and fragrance ingredient, contributing fruity and sulfur-containing nuances characteristic of certain natural foods.
Where is ethyl methyl mercaptopropionate naturally found and how is it used in products?
This compound is naturally present in various foods such as beer, brandy, Parmesan cheese, kiwi fruit, passion fruit juice, pineapple, malt whiskey, and white wine. In applied settings, it is used primarily as a flavoring agent in bakery goods, beverages, cheeses, tropical fruit flavorings, confectionery, and soft desserts. It enhances aroma complexity, particularly sulfurous and fruity notes, aligning with the sensory profiles of these natural sources.
What are the regulatory considerations and recommended usage levels for ethyl methyl mercaptopropionate?
Ethyl methyl mercaptopropionate is recognized under FEMA (US) with the number 3343 and considered generally recognized as safe (GRAS) for flavoring uses. The IFRA (Global) Code of Practice limits its use to a maximum of 0.05% in fragrance concentrates to manage exposure. Usage levels in food products vary but are typically low, for example, up to 2 ppm in bakery and confectionery and 1 ppm in beverages and desserts. Safety data indicate low toxicity, but appropriate handling to avoid eye and skin irritation is recommended.
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 |
| CHEBI: | View |
| HMDB (The Human Metabolome Database): | HMDB40413 |
| FooDB: | FDB020145 |
| Export Tariff Code: | 2930.90.4950 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | Ethyl 3-methylthiopropionate |
General Material Information
| Preferred name | ethyl methyl mercaptopropionate |
| Trivial Name | Ethyl 3-methylthiopropionate |
| Short Description | ethyl 3-methylthiopropionate |
| Formula | C6 H12 O2 S |
| CAS Number | 13327-56-5 |
| FEMA Number | 3343 |
| Flavis Number | 12.053 |
| ECHA Number | 236-370-7 |
| FDA UNII | 1AVT374NII |
| Nikkaji Number | J213.846H |
| MDL | MFCD00039900 |
| COE Number | 11476 |
| xLogP3-AA | 1.10 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 476 ethyl 3-methylthiopropionate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 13327-56-5 ; ETHYL 3-METHYLTHIOPROPIONATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 148.22503662109 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.571 to 8.612 |
| Refractive Index | 1.457 to 1.463 @ 20 °C |
| Boiling Point | 196 to 197°C @ 760 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.324 mmHg @ 25 °C |
| Vapor Density | 5.1 |
| Flash Point TCC Value | 78.89 °C TCC |
| logP (o/w) | 1.352 est |
| Shelf life | 24 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| alcohol | Yes |
| water, 4534 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Sulfurous | |
| sulfurous, metallic, pineapple, fruity, ripe, pulpy, tomato | |
| General comment | At 0.10 % in propylene glycol. sulfury metallic pineapple fruity ripe pulpy tomato |
| Mosciano, Gerard P&F 19, No. 1, 27, (1994) | Sulfureous, metallic, pineapple, fruity ripe, pulpy and tomato |
| Flavor Type: Sulfurous | |
| sulfurous, onion, garlic, pineapple, rummy, vegetable | |
| Mosciano, Gerard P&F 19, No. 1, 27, (1994) | At 30.00 ppm. Sulfureous, onion garlic, pineapple, rumy, vegetative |
| Used in bakery and soft confection at 2ppm, and desserts and beverages at 1ppm. | Fruity |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Citrus , Passion fruit , Pineapple |
| Flavoring purposes | Bakery , Beverage , Cheese , Fruit tropical fruit , Tomato , Vegetable |
| Other purposes | Confection |
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 36/37/39 - 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: | |
| gavage-rat LD50 [sex: M,F] > 5000 mg/kg (Panasevich et al., 1980) | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavor and fragrance agents | |||
| RIFM Fragrance Material Safety Assessment: Search | |||
| IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice | |||
| Recommendation for ethyl methyl mercaptopropionate usage levels up to: | |||
| 0.0500 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 24.00 (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: 6 | |||
| Click here to view publication 6 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 2.00000 | |
| beverages(nonalcoholic): | - | 1.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 1.00000 | |
| fruit ices: | - | 1.00000 | |
| gelatins / puddings: | - | 1.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 2.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | 1.00000 | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| 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): |
| 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 Substance Registry Services (TSCA):13327-56-5 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :61592 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| ethyl 3-methylsulfanylpropanoate |
| Chemidplus:0013327565 |