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ethyl pyruvate
Ethyl pyruvate is an ester compound with a fruity, sweet rummy odor used in flavors and fragrances, found naturally in various foods and beverages.
General Material Description
Ethyl pyruvate is a clear, colorless organic ester with the molecular formula C5H8O3. Known by several synonyms including ethyl 2-oxopropanoate and ethyl alpha-ketopropionate, it is characterized by its distinct rummy, fruity, and ethereal odor profile. Classified as a flavor and fragrance compound, ethyl pyruvate is referenced in chemical databases such as PubChem (PubChem CID 12041). This ester is naturally present in a variety of foods and beverages including grape brandy, wheat bread, cocoa, and white wine. It can be sourced through synthetic or natural extraction methods and finds use in flavor formulation and perfumery.
Occurrence, Applicability & Potential Uses
Ethyl pyruvate occurs naturally in several food products and beverages such as brandy, wheat bread, cocoa, and white wine. It imparts characteristic fruity, sweet, and rummy notes, making it valuable as a flavoring agent in baked goods, caramel, cake, and wine-related products. This compound is also used in fragrance compositions for its ethereal, sweet aroma contributing to butterscotch, chocolate, maple, saffron, vanilla, and wine scent profiles. Its use is regulated under standards including FEMA (US), which categorizes it as a generally recognized as safe (GRAS) flavoring substance. The IFRA (Global) Code of Practice recommends usage limits up to 2% in fragrance concentrates, ensuring safe application in consumer products.
Physico-Chemical Properties Summary
Ethyl pyruvate exhibits a molecular weight of approximately 116.12 g/mol and has a clear liquid appearance. It possesses a moderate flash point of 114 °F (approximately 46 °C), indicating flammability precautions. The substance shows specific gravity values ranging from 1.035 to 1.06 at 20 °C and a refractive index between 1.395 and 1.41 at the same temperature, which inform handling and formulation parameters. Its vapor pressure at 25 °C is low (around 3.094 mmHg), influencing volatility during use. Ethyl pyruvate is soluble in alcohol and has limited water solubility as estimated at 259,000 mg/L at 25 °C but is generally insoluble in pure water. These properties guide its incorporation in flavor and fragrance matrices and storage, which requires cool, dry conditions protected from heat and light to maintain stability over at least 24 months.
FAQ
What is ethyl pyruvate and what are its key characteristics?
Ethyl pyruvate is an ester known chemically as ethyl 2-oxopropanoate with the formula C5H8O3. It has a clear, colorless appearance and features a rummy, fruity, and ethereal odor. This compound is used primarily as a flavor and fragrance ingredient due to its sweet aroma profile. It naturally occurs in products like brandy, wheat bread, cocoa, and white wine.
Where does ethyl pyruvate occur naturally, and how is it used in industry?
Ethyl pyruvate is found in various natural food sources including grape brandy, wheat bread, cocoa, and white wine. Industry uses this compound to impart characteristic fruity and rummy flavors in baked goods, caramel, cakes, and beverages. In perfumery, it contributes to notes such as butterscotch, chocolate, maple, and saffron. Its physicochemical properties allow its incorporation into complex flavor and fragrance formulations.
What regulatory standards and safety information apply to ethyl pyruvate?
Ethyl pyruvate is regulated by FEMA (US) as a generally recognized as safe (GRAS) flavoring substance and is also subject to IFRA (Global) guidelines, which recommend maximum usage levels of up to 2% in fragrance concentrates. Safety data classify it as a flammable irritant requiring precautions such as avoiding skin contact and ignition sources. Extended stability is obtained by storing in cool, dry, well-sealed containers away from heat and light. Its safety in use has been reviewed by fragrance industry bodies including RIFM.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
| Google Scholar | Start search |
| Google Books | Start search |
| Google Patents | Start search |
| Perfumer & Flavorists | Start search |
| EU Patents | Start search |
| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| ethyl 2-oxopropanoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 617-35-6 |
| Pubchem (cid): | 12041 |
| Pubchem (sid): | 134978067 |
| Publications by J-Stage | |
| Higher Hypochlorous Acid Scavenging Activity of Ethyl Pyruvate Compared to Its Sodium Salt | |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB31643 |
| FooDB: | FDB008294 |
| Export Tariff Code: | 2918.30.9000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | ethyl pyruvate |
| Trivial Name | Ethyl pyruvate |
| Short Description | pyruvic acid, ethyl ester |
| Formula | C5 H8 O3 |
| CAS Number | 617-35-6 |
| FEMA Number | 2457 |
| Flavis Number | 9.442 |
| ECHA Number | 210-511-2 |
| FDA UNII | 03O98E01OB |
| Nikkaji Number | J1.665I |
| Beilstein Number | 1071466 |
| MDL | MFCD00009123 |
| COE Number | 430 |
| xLogP3-AA | 0.40 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 938 ethyl pyruvate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 617-35-6 ; ETHYL PYRUVATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 116.11636352539 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.622 to 8.831 |
| Refractive Index | 1.395 to 1.41 @ 20 °C |
| Acid Value | 2 max KOH/g |
| Vapor Pressure | 3.094 mmHg @ 25 °C |
| Flash Point TCC Value | 45.56 °C TCC |
| logP (o/w) | 0.351 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, 2.59e+005 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Ethereal | |
| ethereal, fruity, sweet, sharp, rummy, vegetable, caramellic | |
| General comment | At 10.00 % in dipropylene glycol. ether fruity sweet sharp rum vegetable caramel |
| Mosciano, Gerard P&F 16, No. 1, 31, (1991) | Etherial, fruity, sweet, with a sharp rum-like top note |
| Flavor Type: Rummy | |
| sweet, rummy, fruity, ethereal | |
| Mosciano, Gerard P&F 16, No. 1, 31, (1991) | At 60.00 ppm. Sweet, rum-like with a fruity etherial nuance |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Butterscotch , Chocolate , Maple , Saffron , Vanilla , Wine |
| Flavoring purposes | Cake , Caramel |
| Cosmetic purposes | Skin conditioning |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 10 - Flammable. R 38 - Irritating to skin. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. S 24 - Avoid contact with skin. 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: | |||
| 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 pyruvate usage levels up to: | |||
| 2.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.61 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 20.00 (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: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 40.00000 | |
| beverages(nonalcoholic): | - | 50.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 20.00000 | 150.00000 | |
| fruit ices: | 20.00000 | 150.00000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 35.00000 | |
| 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
| 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 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab) View page or View pdf |
| EPI System: View |
| ClinicalTrials.gov:search |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):617-35-6 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :12041 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 3272 |
| WGK Germany:3 |
| ethyl 2-oxopropanoate |
| Chemidplus:0000617356 |