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ethyl 3-oxohexanoate
Ethyl 3-oxohexanoate is a green, sweet, fruity ester used primarily in food flavorings like apple and pineapple.
General Material Description
Ethyl 3-oxohexanoate is a chemical compound classified as an ester with the molecular formula C8H14O3. It appears as a clear liquid with a distinctive green, sweet, and fruity odor. This ester is known by several synonyms including butyrylacetic acid ethyl ester and ethyl beta-ketohexanoate. It belongs to the class of beta-keto esters and is linked under the controlled vocabulary database CHEBI (Chemical Entities of Biological Interest) under CHEBI:18119. Derived typically via synthetic routes in chemical manufacturing, ethyl 3-oxohexanoate is used mainly for its sensory properties in flavor applications. It can be sourced as a synthetic ingredient but is also identified naturally in certain fruits such as tamarillo. The compound's sweet fruity aroma makes it valuable in flavor design for food products.
Occurrence, Applicability & Potential Uses
Ethyl 3-oxohexanoate occurs naturally in the tamarillo fruit and has been identified as a contributor to its characteristic aroma. It is applied widely in the flavor industry as a flavoring agent to impart green, fruity, and sweet notes. Its uses include flavor enhancement in apple and green apple flavor profiles, cake, fruit punch, orange, and pineapple flavored products. Regulatory standards such as FEMA (US) govern its use limits in foods, classifying it with FEMA number 3683 as generally recognized as safe (GRAS) within specified concentration ranges. The compound's sensory attributes make it valuable for both natural and synthetic flavor formulations.
Physico-Chemical Properties Summary
Ethyl 3-oxohexanoate is a clear liquid exhibiting moderate volatility with a vapor pressure of approximately 0.243 mmHg at 25 °C. Its specific gravity ranges between 0.974 and 0.98 at 25 °C, reflecting near water densities. The refractive index lies between 1.417 and 1.427 at 20 °C, consistent with typical esters. Its flash point is around 78 °C (173 °F), indicating moderate flammability. The compound shows modest lipophilicity with an estimated logP of 1.386, suggesting good solubility in fats and alcohols while being slightly soluble in water (approx. 15 g/L at 25 °C). These properties influence its behavior in flavor formulations affecting volatility, solubility, and stability.
FAQ
What is ethyl 3-oxohexanoate and what are its main characteristics?
Ethyl 3-oxohexanoate is an ester with the molecular formula C8H14O3, recognized for its sweet, green, and fruity odor profile. It is used primarily as a flavoring agent in various food products. The compound is also known by synonyms such as ethyl butyrylacetate and ethyl beta-ketohexanoate. It exists as a clear liquid with moderate volatility and solubility in alcohols and fats but only slight solubility in water.
Where does ethyl 3-oxohexanoate occur naturally and how is it used in industry?
This ester naturally occurs in the tamarillo fruit and contributes to its aroma. Industrially, it is used as a flavor ingredient to impart fruity and green notes in foods such as apples, pineapples, cakes, and fruit punches. Its sensory profile and regulatory acceptance under FEMA (US) facilitate its use as a food flavoring additive in both natural and synthetic flavor formulations.
What regulations and safety considerations apply to ethyl 3-oxohexanoate?
Ethyl 3-oxohexanoate is listed under FEMA number 3683 and is considered generally recognized as safe (GRAS) within defined usage levels for flavoring in food products as per FEMA (US) standards. It has a rat oral LD50 exceeding 300 mg/kg, indicating low acute toxicity. Usage levels are set across various food categories such as baked goods, beverages, and confectionery to ensure safety. Ingredients containing this ester must comply with regulations like REACH (EU) and FDA substance listings.
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 |
| KEGG (GenomeNet): | C02975 |
| HMDB (The Human Metabolome Database): | HMDB31307 |
| FooDB: | FDB003363 |
| Export Tariff Code: | 2918.30.9000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | Ethyl 3-oxohexanoate |
General Material Information
| Preferred name | ethyl 3-oxohexanoate |
| Trivial Name | Ethyl 3-oxohexanoate |
| Short Description | hexanoic acid, 3-oxo-, ethyl ester |
| Formula | C8 H14 O3 |
| CAS Number | 3249-68-1 |
| FEMA Number | 3683 |
| Flavis Number | 9.542 |
| ECHA Number | 221-835-9 |
| FDA UNII | 8Q1AHG710E |
| Nikkaji Number | J100.919B |
| Beilstein Number | 0507689 |
| MDL | MFCD00009401 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 602 ethyl 3-oxohexanoate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 3249-68-1 ; ETHYL 3-OXOHEXANOATE |
| Synonyms |
|
Suppliers
| BOC Sciences | EMD Millipore |
| Inoue Perfumery | Penta International |
| Santa Cruz Biotechnology | Sigma-Aldrich |
| Synerzine | TCI AMERICA |
| Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 158.19717407227 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.105 to 8.155 |
| Refractive Index | 1.417 to 1.427 @ 20 °C |
| Vapor Pressure | 0.243 mmHg @ 25 °C |
| Flash Point TCC Value | 78.33 °C TCC |
| logP (o/w) | 1.386 est |
| Solubility | |
| alcohol | Yes |
| fats | Yes |
| water, slightly | Yes |
| water, 1.508e+004 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Green | |
| sweet, green, sweaty, fruity, berry | |
| General comment | At 100.00 %. sweet green sweaty fruity berry |
| Mosciano, Gerard P&F 15, No. 1, 19, (1990) | Sweet, green, sweaty with fruity notes |
| Flavor Type: Fruity | |
| fruity, pineapple, green, sweet, licorice, vanilla | |
| Mosciano, Gerard P&F 15, No. 1, 19, (1990) | At 50.00 ppm. Fruity, pineapple, green with sweet licorice and vanilla notes |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Flavoring purposes | Apple green apple , Cake , Fruit punch , Orange , Pineapple |
Safety Information
Safety information
| Preferred SDS: View | |
| 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: | |
| oral-rat LD50 > 300 mg/kg United States Patent Document. Vol. #5217973 oral-mouse LD50 8000 mg/kg (Pellmont, 1973a) | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for ethyl 3-oxohexanoate usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.024 (μg/capita/day) | ||
| 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: 13 | |||
| Click here to view publication 13 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 5.00000 | |
| beverages(nonalcoholic): | - | 1.50000 | |
| beverages(alcoholic): | - | 3.00000 | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | 3.00000 | |
| egg products: | - | - | |
| fats / oils: | - | 2.50000 | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | 2.50000 | |
| gelatins / puddings: | - | 3.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 7.50000 | |
| 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): |
| Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to - Flavouring Group Evaluation 10: 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 - (Commission Regulation (EC) No 1565/2000 of 18 July 2000) View page or View pdf |
| Flavouring Group Evaluation 10, Revision 1 (FGE10 Rev1)[1] - 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 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 10, Revision 2 (FGE.10Rev2): 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 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
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| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :238498 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| ethyl 3-oxohexanoate |
| Chemidplus:0003249681 |
| RTECS:MO8420500 for cas# 3249-68-1 |