Articles:
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Notes:
Flavouring agent. Present in strawberry, yellow passion fruit juice and coffee
The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and aminopyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food. (Wikipedia) The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is mainly used as a chemical intermediate in the production of a wide variety of compounds, such as amino acids, analgesics, antibiotics, antimalarial agents, antipyrine and aminopyrine, and vitamin B1; as well as the manufacture of dyes, inks, lacquers, perfumes, plastics, and yellow paint pigments. Alone, it is used as a flavoring for food. (Wikipedia)
| Fragrance Demo Formulas | ||
| Name: | ethyl 3-oxobutanoate | |
| CAS Number: | 141-97-9 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 205-516-1 | |
| FDA UNII: | IZP61H3TB1 | |
| Nikkaji Web: | J4.493H | |
| Beilstein Number: | 0385838 | |
| MDL: | MFCD00009199 | |
| FEMA Number: | 2415 | |
| CoE Number: | 240 | |
| XlogP3: | 0.20 (est) | |
| Molecular Weight: | 130.14330000 | |
| Formula: | C6 H10 O3 | |
| BioActivity Summary: | listing | |
| NMR Predictor: | Predict (works with chrome or firefox) | |
Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
| Google Scholar: | Search |
| Google Books: | Search |
| Google Scholar: with word "volatile" | Search |
| Google Scholar: with word "flavor" | Search |
| Google Scholar: with word "odor" | Search |
| Perfumer and Flavorist: | Search |
| Google Patents: | Search |
| US Patents: | Search |
| EU Patents: | Search |
| Pubchem Patents: | Search |
| PubMed: | Search |
| NCBI: | Search |
| JECFA Food Flavoring: | 595 ethyl acetoacetate |
| Flavis Number: | 09.402 (Old) |
| DG SANTE Food Flavourings: | 09.402 ethyl acetoacetate |
| FEMA Number: | 2415 ethyl acetoacetate |
| FDA Mainterm: | ETHYL ACETOACETATE |
| FDA Regulation: | |
| FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Subpart F--Flavoring Agents and Related Substances Sec. 172.515 Synthetic flavoring substances and adjuvants. FDA PART 175 -- INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS Subpart C--Substances for Use as Components of Coatings Sec. 175.300 Resinous and polymeric coatings. | |
Physical Properties:
| Appearance: | colorless to yellow clear liquid (est) |
| Assay: | 99.00 to 100.00 % |
| Food Chemicals Codex Listed: | Yes |
| Specific Gravity: | 1.02200 to 1.02710 @ 25.00 °C. |
| Pounds per Gallon - (est).: | 8.504 to 8.546 |
| Refractive Index: | 1.41800 to 1.42100 @ 20.00 °C. |
| Melting Point: | -45.40 to -44.00 °C. @ 760.00 mm Hg |
| Boiling Point: | 180.00 to 181.00 °C. @ 760.00 mm Hg |
| Boiling Point: | 100.00 to 101.00 °C. @ 50.00 mm Hg |
| Acid Value: | 5.00 max. KOH/g |
| PH Number: | 3.80 |
| Vapor Pressure: | 0.890000 mmHg @ 25.00 °C. (est) |
| Vapor Density: | 4.48 ( Air = 1 ) |
| Flash Point: | 184.00 °F. TCC ( 84.44 °C. ) |
| logP (o/w): | 0.250 |
| Shelf Life: | 24.00 month(s) or longer if stored properly. |
| Storage: | store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Soluble in: | |
| alcohol | |
| isopropyl myristate | |
| most organic solvents | |
| water, 110000 mg/L @ 17C (exp) | |
| Insoluble in: | |
| paraffin oil | |
| water | |
| Similar Items: note | |
| amyl acetoacetate | |
| isoamyl acetoacetate | |
| para-anisyl acetoacetate | |
| benzyl acetoacetate | |
| bergamot acetoacetate | |
| butyl acetoacetate | |
| isobutyl acetoacetate | |
| cinnamyl acetoacetate | |
| cyclohexyl acetoacetate | |
| dodecyl acetoacetate | |
| ethyl 2-ethyl acetoacetate | |
| geranyl acetoacetate | |
| heptyl acetoacetate | |
| (Z)-3-hexen-1-yl acetoacetate | |
| hexyl acetoacetate | |
| jasmin acetoacetate | |
| laevo-menthyl acetoacetate | |
| methyl acetoacetate | |
| spicy acetoacetate | |
Organoleptic Properties:
| Odor Type: | fruity |
| Odor Strength: | medium |
| Odor Description: at 100.00 %. | fresh fruity green apple fatty |
| Substantivity: | 4 Hour(s) |
Cosmetic Information:
| CosIng: | cosmetic data |
| Cosmetic Uses: |
perfuming agents |
Safety 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 - Wear suitable protective clothing. | |
| Human Experience: | 8 % solution: non-sensitising. |
| Oral/Parenteral Toxicity: | |
|
oral-rat LD50 3980 mg/kg (Smyth et al., 1949) oral-mouse LD50 5105 mg/kg Journal of Pharmaceutical Sciences. Vol. 60, Pg. 1810, 1971. oral-rat LD50 3980 mg/kg Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 60, 1949. | |
| Dermal Toxicity: | |
|
skin-rabbit LD50 > 5000 mg/kg Journal of Industrial Hygiene and Toxicology. Vol. 31, Pg. 60, 1949. skin-rabbit LD > 20 mL/kg Union Carbide Data Sheet. Vol. 3/12/1969 | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in Use Information:
| Category: | flavor and fragrance agents | ||
| Recommendation for ethyl acetoacetate usage levels up to: | |||
| 15.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1200.00 (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: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 120.00000 | |
| beverages(nonalcoholic): | - | 17.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 530.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 24.00000 | |
| fruit ices: | - | 24.00000 | |
| gelatins / puddings: | - | 93.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 110.00000 | |
| 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): | |
| 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 | |
| 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 | |
| Scientific Opinion on Flavouring Group Evaluation 92 (FGE.92): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (68th 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 evaluated by EFSA in FGE.10Rev1 (2009) 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 |
| ECHA (ESR): | View |
| NIOSH International Chemical Safety Cards: | search |
| NLM Hazardous Substances Data Bank: | Search |
| Chemical Carcinogenesis Research Information System: | Search |
| AIDS Citations: | Search |
| Toxicology Citations: | Search |
| Env. Mutagen Info. Center: | Search |
| EPA Substance Registry Services (TSCA): | 141-97-9 |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 8868 |
| National Institute of Allergy and Infectious Diseases: | Data |
| WGK Germany: | 1 |
| ethyl 3-oxobutanoate | |
| Chemidplus: | 0000141979 |
| EPA/NOAA CAMEO: | hazardous materials |
| RTECS: | 141-97-9 |
References:
| ethyl 3-oxobutanoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 141-97-9 |
| Pubchem (cid): | 8868 |
| Pubchem (sid): | 134973060 |
Other Information:
| (IUPAC): | Atomic Weights of the Elements 2009 |
| (IUPAC): | Atomic Weights of the Elements 2009 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| FDA Everything Added to Food in the United States (EAFUS): | View |
| CHEBI: | View |
| CHEMBL: | View |
| KEGG (GenomeNet): | C03500 |
| HMDB (The Human Metabolome Database): | HMDB31218 |
| FooDB: | FDB003241 |
| Export Tariff Code: | 2918.30.9000 |
| Haz-Map: | View |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| RSC Learn Chemistry: | View |
| FAO: | Ethyl acetoacetate |
| Formulations/Preparations: grades: technical; 98%. | |
Potential Blenders and core components note
Potential Uses:
| agrumen aldehyde | FR | |
| almond | FR | |
| almond blossom | FR | |
| apple | FR | |
| apple blossom | FR | |
| brandy apple brandy | FL | |
| crabapple | FR | |
| apple green apple | FR | |
| apple red apple | FR | |
| arrack | FL | |
| banana | FR | |
| brandy | FL | |
| bubble gum | FR | |
| cherry | FR | |
| cherry maraschino cherry | FL | |
| cherry wild cherry | FL | |
| citrus | FR | |
| cloudberry bakeapple | FL | |
| coffee | FR | |
| cologne | FR | |
| crabapple blossom | FR | |
| eglantine | FR | |
| fig | FR | |
| fruit tropical fruit | FL | |
| gardenia | FR | |
| green | FR | |
| herbal | FR | |
| hibiscus | FR | |
| lemon | FR | |
| marigold | FL/FR | |
| melon | FR | |
| myrtle oil replacer | FR | |
| orange | FR | |
| passion blossom | FR | |
| passion fruit | FR | |
| peach | FR | |
| pear | FR | |
| pear blossom | FR | |
| pineapple | FR | |
| pomegranate | FR | |
| raspberry | FR | |
| rose wild rose | ||
| sherry | FR | |
| spring rain | FR | |
| stephanotis | FR | |
| strawberry | FR | |
| strawberry leaf | ||
| tea | FL | |
| topnotes | ||
| tropical | FL | |
| valerian | FL/FR | |
| wine | FR |
Occurrence (nature, food, other): note
| coffee Search PMC Picture | |
| passion fruit Search Trop Picture | |
| strawberry wild strawberry fruit 4 ppm Search Trop Picture |
Synonyms:
| acetoacetic acid ethyl ester | |
| acetoacetic acid ethylester | |
| acetoacetic ester | |
| 3-oxo | butanoic acid ethyl ester |
| 3-oxo- | butanoic acid ethyl ester |
| butanoic acid, 3-oxo-, ethyl ester | |
| 3-oxo | butanoic acid, ethyl ester |
| 3-oxo- | butyric acid ethyl ester |
| diacetic ether | |
| EAA | |
| 1- | ethoxybutane-1,3-dione |
| ethyl 3-ketobuyrate | |
| ethyl 3-oxo-butyrate | |
| ethyl 3-oxobutanoate | |
| ethyl 3-oxobutyrate | |
| ethyl aceto acetate | |
| ethyl aceto acetate FCC | |
| ethyl aceto acetate natural | |
| ethyl acetoacetate natural | |
| ethyl acetoacetate redistilled FCC | |
| ethyl acetyl acetate | |
| ethyl acetyl acetonate | |
| ethyl beta-ketobutyrate | |
| ethyl-acetoacetate |