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ethyl 2-furoate
Ethyl 2-furoate is a naturally occurring ester characterized by balsamic odor and burnt flavor notes, primarily utilized as a flavoring agent in food and beverages.
General Material Description
Ethyl 2-furoate is an organic ester compound with the molecular formula C7H8O3 that belongs to the class of furan derivatives. It typically appears as a clear liquid possessing a distinct balsamic odor combined with burnt and fruity floral sensory notes. Known also by several synonyms such as 2-carboethoxyfuran and ethyl furan-2-carboxylate, it is cataloged under the PubChem controlled vocabulary. This compound occurs naturally in various fruits and fermented beverages, where it contributes characteristic aromas. Industrially, ethyl 2-furoate is obtained via chemical synthesis or extraction from natural sources. Its flavor profile makes it a valuable additive in food and beverage flavorings, especially to impart tropical, balsam, or fruity nuances.
Occurrence, Applicability & Potential Uses
Ethyl 2-furoate naturally occurs in a range of fruits including guava, kiwi, and papaya, albeit at low concentrations typically below 0.05 mg/kg. It is also present in fermented alcoholic beverages such as beer, brandy, rum, and wines including port wine, with trace levels up to approximately 0.3 mg/kg reported. This compound is principally applied as a flavoring agent, contributing balsamic, floral, berry, oriental, and fruit notes to flavor formulations. Flavor industry standards, such as FEMA (US), recognize ethyl 2-furoate for its safe flavor usage within prescribed limits. Its presence in diverse foodstuffs aligns with its acceptance as a flavoring additive in compliance with various food safety authorities.
Physico-Chemical Properties Summary
Ethyl 2-furoate exhibits several physical and chemical properties that influence its behavior in flavor formulations. It has a melting point range of 35 to 37 °C at standard atmospheric pressure and a moderate specific gravity of approximately 1.117 at 25 °C. Its vapor pressure is relatively low at 0.391 mmHg measured at 25 °C, indicating moderate volatility which favors stable aroma release. The compound’s logP of 1.52 suggests balanced lipophilicity, enhancing solubility in both organic solvents and limited water solubility estimated at 4210 mg/L at 25 °C. It dissolves readily in alcohols, a characteristic beneficial for flavor blending. The flash point is reported as 158 °F (approximately 70 °C), pointing to moderate flammability risks under elevated temperatures. These properties inform its application parameters and formulation compatibility in flavor systems.
FAQ
What is ethyl 2-furoate and how is it classified?
Ethyl 2-furoate is an organic ester compound derived from 2-furoic acid and ethanol. It belongs to the class of furan derivatives characterized by a heterocyclic aromatic ring containing oxygen. This ester is recognized for its naturally occurring presence in various fruits and fermented beverages and is primarily used as a flavoring agent in the food industry due to its distinct balsamic and fruity sensory properties.
Where is ethyl 2-furoate commonly found and how is it used in products?
Ethyl 2-furoate is commonly detected in low quantities within fruits such as guava, kiwi, and papaya, as well as in alcoholic beverages including beer, brandy, rum, and wines. Its flavor profile, described as balsamic with burnt and fruity floral notes, makes it valuable in flavor formulations to impart tropical, berry, and oriental characteristics. It is utilized predominantly as a flavoring agent in food and beverage products within recommended usage levels established by regulatory bodies.
What are the safety and regulatory considerations for using ethyl 2-furoate?
Ethyl 2-furoate is evaluated by flavor industry regulatory standards including FEMA (US), which recognize it as safe for use within specified concentrations in food products. Safety data indicate no significant hazard classifications under OSHA regulations. Usage levels are carefully prescribed, with recommended maximum daily intake values established based on toxicological evaluations. Adequate No-Observed-Adverse-Effect-Level (NOAEL) data support its controlled application. It is not recommended for fragrance use and all formulations should comply with relevant food safety and flavoring regulations.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| ethyl furan-2-carboxylate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 614-99-3 |
| Pubchem (cid): | 11980 |
| Pubchem (sid): | 134977290 |
| Publications by US Patents | |
| 3,952,024 - Furfurylthioacetone | |
| Flavoring agent | |
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 |
| HMDB (The Human Metabolome Database): | Search |
| Export Tariff Code: | 2932.19.5100 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| EFSA Update of results on the monitoring of furan levels in food: | Read Report |
| EFSA Previous report: Results on the monitoring of furan levels in food: | Read Report |
| EFSA Report of the CONTAM Panel on provisional findings on furan in food: | Read Report |
General Material Information
| Preferred name | ethyl 2-furoate |
| Trivial Name | Ethyl 2-furoate |
| Short Description | 2-furancarboxylic acid, ethyl ester |
| Formula | C7 H8 O3 |
| CAS Number | 614-99-3 |
| Flavis Number | 13.122 |
| ECHA Number | 210-404-0 |
| FDA UNII | S1H449R92T |
| Nikkaji Number | J7.026B |
| Beilstein Number | 0002653 |
| MDL | MFCD00003237 |
| COE Number | 10588 |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 140.13836669922 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | |
| Melting Point | 35 to 37°C @ 760 mm Hg |
| Vapor Pressure | 0.391 mmHg @ 25 °C |
| Flash Point TCC Value | 70 °C TCC |
| logP (o/w) | 1.52 |
| Solubility | |
| alcohol | Yes |
| water, 4210 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Balsamic | |
| balsamic, fruity, floral, orchid | |
| General comment | At 10.00 % in dipropylene glycol. ethyl benzoate fruity floral |
| Flavor Type: Burnt | |
| burnt | |
| General comment | Burnt |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Balsam , Berry , Floral , Fruit , Oriental |
| Flavoring purposes | Tropical |
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: | |
| intravenous-mouse LD50 180 mg/kg NIOSH Exchange Chemicals. Vol. NX#00372 intraperitoneal-rat LDLo 75 mg/kg Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 174, 1936. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for ethyl 2-furoate usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.39 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 3900 (μg/person/day) | ||
| Adequate NOAEL exists: | Yes | ||
| Threshold of Concern: | 540 (μg/person/day) | ||
| Structure Class: | II | ||
| Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i). | |||
| Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm. | |||
| average usage mg/kg | maximum usage mg/kg | ||
| Dairy products, excluding products of category 02.0 (01.0): | 7.00000 | 35.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 5.00000 | 25.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 10.00000 | 50.00000 | |
| Processed fruit (04.1): | 7.00000 | 35.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 10.00000 | 50.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 5.00000 | 25.00000 | |
| Bakery wares (07.0): | 10.00000 | 50.00000 | |
| Meat and meat products, including poultry and game (08.0): | 2.00000 | 10.00000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 2.00000 | 10.00000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 5.00000 | 25.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 10.00000 | 50.00000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 5.00000 | 25.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 10.00000 | 50.00000 | |
| Ready-to-eat savouries (15.0): | 20.00000 | 100.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 5.00000 | 25.00000 | |
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) related to Flavouring Group Evaluation 13 (FGE.13); Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 (Commission Regulation (EC) No 1565/2000 of 18 View page or View pdf |
| Flavouring Group Evaluation 66 (FGE.66)[1]:Consideration of furfuryl alcohol and related flavouring substances evaluated by JECFA (55th meeting) structurally related to Furfuryl and furan derivatives with and without additional side chain substituents and heteroatoms evaluated by EFSA in FGE.13 (2005) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 13Rev1: Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 View page or View pdf |
| Consideration of sulfur-substituted furan derivatives used as flavouring agents evaluated by JECFA (59th meeting) structurally related to a subgroup of substances within the group of Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 evaluated by EFSA in FGE.13Rev1 (2009) View page or View pdf |
| Flavouring Group Evaluation 67 (FGE.67): Consideration of 40 furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by JECFA at the 65th meeting (JECFA, 2006b) and re-evaluated at the 69th meeting (JECFA, 2009c) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 13, Revision 2 (FGE.13Rev2): Furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 67, Revision 1 (FGE.67Rev.1): Consideration of 40 furan-substituted aliphatic hydrocarbons, alcohols, aldehydes, ketones, carboxylic acids and related esters, sulfides, disulfides and ethers evaluated by JECFA at the 65th meeting (JECFA, 2006b) and re-evaluated at the 69th meeting (JECFA, 2009c) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 13 Revision 3 (FGE.13Rev3): furfuryl and furan derivatives with and without additional side-chain substituents and heteroatoms from chemical group 14 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):614-99-3 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :11980 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| ethyl furan-2-carboxylate |
| Chemidplus:0000614993 |
| RTECS:LV1850000 for cas# 614-99-3 |