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ethyl anthranilate
Ethyl anthranilate is an aromatic ester with a medium-strength floral odor and fruity flavor used primarily in flavor and fragrance applications.
General Material Description
Ethyl anthranilate, also known as ethyl o-aminobenzoate, is a colorless to pale yellow aromatic ester of anthranilic acid, with the chemical formula C9H11NO2. It possesses a distinctive medium-strength floral odor coupled with sweet, fruity, and minty nuances, making it valuable in sensory applications. This compound appears in the flavor and fragrance industry under various synonyms, including 2-amino-benzoic acid ethyl ester and anaesthesine. It is listed in the Food Chemicals Codex, reflecting its status as a recognized flavoring agent. Ethyl anthranilate can be sourced naturally from fruits such as grape, orange, and star fruit, or produced synthetically for controlled-quality use in formulations. For chemical information and structural data, it is referenced in databases like PubChem.
Occurrence, Applicability & Potential Uses
Ethyl anthranilate naturally occurs in several fruits, including concord grapes, orange fruit juice and peel, and star fruit. Its presence in these sources contributes to their characteristic aromatic profiles. The compound is widely applied as a flavor and fragrance agent, enhancing products with its floral, grape-like, and fruity nuances. It is commonly utilized in the formulation of perfumes and various flavor systems, such as those mimicking coconut, root beer, cola, apricot, grape, and peach. Regulatory assessments such as FEMA (US) provide guidelines for its maximum use levels, ensuring safe incorporation into consumer products. Its ability to blend well with other aromatic molecules underlies its versatility in both food and cosmetic industries.
Physico-Chemical Properties Summary
Ethyl anthranilate exhibits physical and chemical properties that influence its function in formulations. It has a molecular weight of approximately 165.19 g/mol and displays moderate volatility with a vapor density around 5.7 and a low vapor pressure at 25 °C of 0.01 mmHg. The compound is a liquid at room temperature, with a melting point between 13 and 14 °C and a boiling point ranging from 129 to 147 °C under reduced pressures. Its specific gravity at 25 °C is about 1.117 to 1.119, and the refractive index at 20 °C spans 1.563 to 1.566. Ethyl anthranilate is soluble in alcohol, fixed oils, propylene glycol, and moderately soluble in water (estimated solubility of 413.6 mg/L at 25 °C). The relatively high logP value of 2.57 indicates moderate lipophilicity, facilitating its use in both aqueous and oily formulations. These physicochemical characteristics support its stability and substantivity in flavor and fragrance compositions.
FAQ
What is ethyl anthranilate and what are its primary characteristics?
Ethyl anthranilate is an aromatic ester derived from anthranilic acid and ethanol. It is recognized by its medium-strength floral odor with sweet, fruity, and minty notes. The compound appears as a clear to pale yellow liquid and has a chemical formula of C9H11NO2. It is also known under several synonyms, including ethyl o-aminobenzoate and anaesthesine. In sensory applications, it contributes floral and grape-like aromas and is documented in chemical databases such as PubChem for reference.
Where is ethyl anthranilate commonly found and how is it used in industry?
Ethyl anthranilate naturally occurs in various fruits, notably concord grapes, orange juice and peel, and star fruit. Industrially, it is used extensively in flavors and fragrances. Its versatility comes from imparting floral, fruity, and grape-like aromas, which enhances products like perfumes, flavorings for beverages, confectionery, and more. It blends well with other compounds and is compatible with flavors such as coconut, root beer, and peach, increasing its utility in diverse product formulations.
What regulations govern the use of ethyl anthranilate, and how is it sourced safely?
Regulatory guidelines for ethyl anthranilate include standards by FEMA (US) concerning usage levels to ensure safety in flavor applications. It is listed as FEMA number 2421 and has been evaluated by JECFA (FAO/WHO). The compound is generally recognized as safe when used within recommended concentrations in foods and fragrances. Safety assessments indicate it is an irritant in concentrated forms but has low toxicity at typical use levels. Both natural extraction from fruit sources and synthetic production methods support secure and controlled availability for commercial use.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| ethyl 2-aminobenzoate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 87-25-2 |
| Pubchem (cid): | 6877 |
| Pubchem (sid): | 134971560 |
| Pherobase: | View |
| Publications by Info | |
| anthranilate derivatives | |
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): | HMDB33589 |
| FooDB: | FDB011666 |
| Export Tariff Code: | 2921.51.5000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Formulations/Preparations: grades: technical: fcc | |
General Material Information
| Preferred name | ethyl anthranilate |
| Trivial Name | Ethyl 2-aminobenzoate |
| Short Description | ethyl o-aminobenzoate |
| Formula | C9 H11 N O2 |
| CAS Number | 87-25-2 |
| FEMA Number | 2421 |
| Flavis Number | 9.716 |
| ECHA Number | 201-735-1 |
| FDA UNII | 38Y050IUE4 |
| Nikkaji Number | J4.276E |
| Beilstein Number | 0878874 |
| MDL | MFCD00007711 |
| COE Number | 251 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1535 ethyl anthranilate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 87-25-2 ; ETHYL ANTHRANILATE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | Yes |
| Molecular weight | 165.19206237793 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.295 to 9.311 |
| Refractive Index | 1.563 to 1.566 @ 20 °C |
| Melting Point | 13 to 14°C @ 760 mm Hg |
| Boiling Point | 129 to 130°C @ 9 mm Hg |
| Boiling Point | 145 to 147°C @ 15 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.01 mmHg @ 25 °C |
| Vapor Density | 5.7 |
| Flash Point TCC Value | 110 °C TCC |
| logP (o/w) | 2.57 |
| Solubility | |
| alcohol | Yes |
| fixed oils | Yes |
| propylene glycol | Yes |
| water, 413.6 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Floral | |
| sweet, floral, grape, orangeflower, wintergreen | |
| Odor strength | medium |
| Substantivity | 28 hour(s) at 100.00 % |
| Luebke, William tgsc, (1996) | At 100.00 %. sweet floral grape orangeblossom wintergreen |
| Flavor Type: Fruity | |
| sweet, fruity, floral, minty, wintergreen | |
| Luebke, William tgsc, (1996) | Sweet fruity floral minty wintergreen |
| Compatible with cuminyl alcohol. Can be used in coconut, root beer, cola, apricot, grape and peach flavors. | Fruity |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Acacia , Berry , Floral , Grape , Jasmin , Mandarin , Narcissus , Neroli , Orange blossom , Oriental , Wintergreen |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 36/38 - Irritating to skin and eyes. 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. | |
| 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. | |
| Human Experience: | |
| 4 % solution: no irritation or sensitization. | |
| Oral/Parenteral Toxicity: | |
| oral-rat LD50 3750 mg/kg Food and Cosmetics Toxicology. Vol. 14, Pg. 759, 1976. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Cosmetics Toxicology. Vol. 14, Pg. 759, 1976. | |
| 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 anthranilate usage levels up to: | |||
| 8.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 12.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 39.00 (μg/capita/day) | ||
| Threshold of Concern: | 1800 (μg/person/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: | - | 23.00000 | |
| beverages(nonalcoholic): | - | 5.90000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 79.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 7.60000 | |
| fruit ices: | - | 7.60000 | |
| gelatins / puddings: | - | 14.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 19.00000 | |
| 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 84, (FGE.84)[1] - Consideration of Anthranilate derivatives evaluated by JECFA (65th meeting) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| EPI System: View |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):87-25-2 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :6877 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| ethyl 2-aminobenzoate |
| Chemidplus:0000087252 |
| EPA/NOAA CAMEO:hazardous materials |
| RTECS:DG2448000 for cas# 87-25-2 |