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ethyl 3-(ethyl thio) butyrate
Ethyl 3-(ethyl thio) butyrate is a chemical flavoring agent known for its metallic fruity odor used primarily in baked goods and confectionery applications.
General Material Description
Ethyl 3-(ethyl thio) butyrate is an organic sulfur-containing ester with the molecular formula C8H16O2S. It appears as a liquid with a characteristic metallic fruity odor at low concentrations, frequently utilized as a flavoring substance. The compound's synonyms include butanoic acid, 3-(ethylthio)-, ethyl ester, and ethyl 3-ethylsulfanylbutanoate, among others. Classified as a flavoring agent under FEMA (US) standards, it is referenced by CAS number 90201-28-8 and can be accessed via chemical databases like PubChem. It is typically derived synthetically and used in various food applications where its odor profile contributes to overall sensory characteristics.
Occurrence, Applicability & Potential Uses
Ethyl 3-(ethyl thio) butyrate naturally does not occur at significant levels in foods but is synthesized for use primarily as a flavoring agent. Its application is recognized under the FEMA (US) GRAS status with FEMA number 4572, permitting use in baked goods, chewing gum, and fruit ices at specific ppm levels. This compound imparts a characteristic metallic fruity note that enhances flavor profiles in confectionery and related food products. Regulations under FEMA guide its use concentration to ensure sensory efficacy without adverse effects. Its role in flavor formulations is mainly to impart distinctive sulfur-containing fruity notes uncommon in standard esters.
Physico-Chemical Properties Summary
Ethyl 3-(ethyl thio) butyrate exhibits physical properties that influence its handling and formulation in industrial settings. It is a liquid with a boiling point range of approximately 230 to 233 °C at atmospheric pressure, alongside a vapor pressure of 0.055 mmHg at 25 °C, indicating low volatility at room temperature. The substance has a specific gravity near 0.98 at 20 °C and a refractive index between 1.454 and 1.46 at the same temperature. Solubility is notable in alcohol and is estimated at around 564 mg/L in water at 25 °C, though it is not readily miscible with water. Its estimated log P value of 2.45 suggests moderate lipophilicity, facilitating solubility in organic matrices. These properties contribute to its stability and sensory delivery in flavor applications. The flash point near 95 °C (203 °F) advises appropriate temperature controls during processing.
FAQ
What is ethyl 3-(ethyl thio) butyrate and what are its main characteristics?
Ethyl 3-(ethyl thio) butyrate is a sulfur-containing ester known for its distinctive metallic fruity odor. Used primarily as a flavoring agent, it imparts nuanced aroma notes appreciated in food products such as baked goods and confectioneries. The compound is a liquid under ambient conditions and is chemically identified by CAS number 90201-28-8. It displays moderate volatility and moderate solubility in water and alcohol. Its molecular formula is C8H16O2S, and it is used for its unique sensory qualities rather than naturally occurring in significant amounts.
How is ethyl 3-(ethyl thio) butyrate typically used and where can it be found?
This compound is mainly a synthetic flavoring agent utilized in the food industry. It is approved by FEMA (US) for use in products such as baked goods, chewing gum, and fruit ices with specific limitations on maximum concentrations to maintain safety and flavor balance. Its usage exploits its metallic fruity aroma to augment sensory profiles in formulated foods. Though it is not commonly found naturally in significant quantities, careful synthetic preparation ensures consistent quality and olfactory effects in formulations.
What regulations and safety standards apply to ethyl 3-(ethyl thio) butyrate?
Ethyl 3-(ethyl thio) butyrate is recognized by FEMA (US) under GRAS status (FEMA number 4572) for use as a flavoring agent with defined concentration limits in various food categories. Safety classification by OSHA (29 CFR 1910) does not assign specific hazard classifications, indicating minimal known hazards under standard conditions. While detailed toxicological data on oral, dermal, and inhalation toxicity are not fully determined, regulatory bodies monitor its usage strictly within approved limits. Manufacturers and users should adhere to FEMA guidelines for flavoring use and consult databases such as ECHA and FDA for updated regulatory status.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| PubMeb | Start search |
| NCBI | Start search |
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): | Search |
| ChemSpider: | View |
| FAO: | Ethyl 3-(ethylthio)butyrate |
General Material Information
| Preferred name | ethyl 3-(ethyl thio) butyrate |
| Trivial Name | Butanoic acid, 3-(ethylthio)-, ethyl ester |
| Short Description | ethyl 3-(ethylthio)butyrate |
| Formula | C8 H16 O2 S |
| CAS Number | 90201-28-8 |
| FEMA Number | 4572 |
| ECHA Number | 290-671-8 |
| FDA UNII | GTO77Z933P |
| Nikkaji Number | J318.977E |
| xLogP3-AA | 1.90 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1922 ethyl 3-(ethylthio)butyrate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 90201-28-8 ; ETHYL 3-(ETHYLTHIO)BUTYRATE |
| Synonyms |
|
Suppliers
| Parchem |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 176.27891540527 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.172 to 8.222 |
| Refractive Index | 1.454 to 1.46 @ 20 °C |
| Boiling Point | 230 to 233°C @ 760 mm Hg |
| Boiling Point | 50 to 52°C @ 2 mm Hg |
| Vapor Pressure | 0.055 mmHg @ 25 °C |
| Flash Point TCC Value | 95 °C TCC |
| logP (o/w) | 2.45 est |
| Solubility | |
| alcohol | Yes |
| water, 564.3 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Metallic | |
| metallic, fruity | |
| General comment | At 0.10 % in propylene glycol. metallic fruity |
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 ethyl 3-(ethyl thio) butyrate usage levels up to: | |||
| not for fragrance use. | |||
| 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: 24 | |||
| Click here to view publication 24 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.30000 | 1.00000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 0.03000 | 0.10000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | 0.00300 | 0.01000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| 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
| 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 :3021670 |
| National Institute of Allergy and Infectious Diseases:Data |
| ethyl 3-ethylsulfanylbutanoate |
| Chemidplus:0090201288 |