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strawberry furanone methyl ether
Strawberry furanone methyl ether is a fruit-derived furanone flavor with sweet, caramellic, and moldy notes used in flavor and fragrance applications.
General Material Description
Strawberry furanone methyl ether, chemically known as 2,5-dimethyl-4-methoxy-3(2H)-furanone (CAS 4077-47-8), is a furanone derivative notable for its distinctive sweet and caramellic aroma with underlying moldy nuances. This pale liquid possesses a molecular formula of C7H10O3 and is widely recognized by synonyms such as mesifuran and berry furanone. It can be found naturally in various fruits including strawberries, raspberries, and mangoes, contributing to their characteristic scent profiles. The compound is extensively utilized in flavor and fragrance industries to impart fruity and caramel notes. More detailed chemical information can be found at PubChem. The methyl ether variant offers distinct aroma properties compared to its parent compound, making it valuable in complex flavor formulations.
Occurrence, Applicability & Potential Uses
Strawberry furanone methyl ether occurs naturally in several fruits such as strawberry, raspberry, blackberry, grape, mango, pineapple, and kiwi. Its presence in these fruits enhances their aromatic profiles by imparting sweet, caramellic, and slightly moldy nuances. The compound is employed in flavor and fragrance formulations to emulate or boost fruity, caramel, nutty, and berry notes. It meets the usage criteria under the FEMA (US) flavoring standards, with FEMA number 3664, highlighting its acceptance for food flavor applications. Due to its potent aroma character, it is used at low concentrations in products like beverages, confectioneries, and baked goods to provide rich strawberry-like and caramel flavor cues.
Physico-Chemical Properties Summary
Strawberry furanone methyl ether exhibits physical properties conducive to flavor formulation, including a boiling point around 221 to 222°C at atmospheric pressure and a specific gravity near 1.09 at 25°C. It has moderate volatility with a vapor pressure of approximately 0.103 mmHg at 25°C, allowing controlled evaporation in fragrance products. The compound's estimated logP of 0.27 indicates moderate lipophilicity, favoring solubility in alcohols but limited solubility in water, which should be considered when designing aqueous formulations. Its flash point measured at 72°C reflects moderate flammability. The refractive index ranges from 1.475 to 1.481 at 20°C, useful for quality control. These combined physicochemical attributes influence handling, formulation, and stability in flavor and fragrance applications.
FAQ
What is strawberry furanone methyl ether and what are its main characteristics?
Strawberry furanone methyl ether, also known as 2,5-dimethyl-4-methoxy-3(2H)-furanone or mesifuran, is a naturally occurring flavor compound found in various fruits such as strawberries and raspberries. It is characterized by a sweet, caramel-like aroma with subtle moldy and fruity undertones. The compound belongs to the furanone chemical family and is widely used in flavor and fragrance industries to impart strawberry and caramel notes. It has a molecular formula of C7H10O3 and is available in both natural and synthetic forms.
In which fruits and products is strawberry furanone methyl ether commonly found or used?
Strawberry furanone methyl ether naturally occurs in several fruits including wild strawberry, raspberry, blackberry, grape, mango, pineapple, and kiwi. Due to its desirable aroma and flavor qualities, it is incorporated into flavorings for beverages, confectioneries, baked goods, and dairy products to provide enhanced fruity and caramel characteristics. Its usage levels are regulated, with FEMA (US) guidelines permitting concentrations up to 0.5% in fragrance concentrates, reflecting its versatility across food and fragrance sectors.
What are the regulatory considerations and safety information for strawberry furanone methyl ether?
Strawberry furanone methyl ether is recognized under FEMA (US) as a Generally Recognized as Safe (GRAS) flavoring substance with FEMA number 3664. Usage levels in food and fragrance applications are recommended to remain within specified limits, typically up to 0.5% in fragrance products. Safety data indicates it is classified as an irritant affecting eyes, respiratory system, and skin, requiring appropriate handling precautions such as protective clothing and avoiding contact. No significant oral, dermal, or inhalation toxicity data are available, and assessments by regulatory bodies including EFSA review its use in flavorings. Full safety documents and exposure guidelines can be accessed through official safety data sheets and regulatory agencies.
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 |
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 |
| HMDB (The Human Metabolome Database): | HMDB34230 |
| FooDB: | FDB012541 |
| Export Tariff Code: | 2932.19.0090 |
| 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 | strawberry furanone methyl ether |
| Trivial Name | 2,5-Dimethyl-4-methoxy-3(2H)-furanone |
| Short Description | 2,5-dimethyl-4-methoxy-3(2H)-furanone |
| Formula | C7 H10 O3 |
| CAS Number | 4077-47-8 |
| Deleted CAS Number | 144831-51-6 |
| FEMA Number | 3664 |
| Flavis Number | 13.089 |
| ECHA Number | 223-797-9 |
| FDA UNII | 3241BIM975 |
| Nikkaji Number | J217.886I |
| MDL | MFCD00209504 |
| xLogP3-AA | 1.00 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1451 2,5-dimethyl-4-methoxy-3(2H)-furanone |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 4077-47-8 ; 2,5-DIMETHYL-4-METHOXY-3(2H)-FURANONE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 142.154296875 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.078 to 9.128 |
| Refractive Index | 1.475 to 1.481 @ 20 °C |
| Boiling Point | 221 to 222°C @ 760 mm Hg |
| Acid Value | 3 max KOH/g |
| Vapor Pressure | 0.103 mmHg @ 25 °C |
| Flash Point TCC Value | 72.22 °C TCC |
| logP (o/w) | 0.269 est |
| Solubility | |
| alcohol | Yes |
| water, 2.441e+004 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Moldy | |
| sweet, moldy, mushroom, vegetable, potato, sugar burnt sugar, nut skin, wasabi, caramellic, fruity, brandy, musty, beany, cocoa, coffee, meaty | |
| Odor strength | high , recommend smelling in a 1.00 % solution or less |
| Substantivity | > 384 hour(s) at 100.00 % |
| Luebke, William tgsc, (2017) | At 1.00 % in dipropylene glycol. sweet moldy mushroom vegetable potato burnt sugar nut skin wasabi caramellic fruity brandy |
| Mosciano, Gerard P&F 24, No. 5, 41, (1999) | At 1.00 % in propylene glycol. Musty, sweet, caramellic, musty beany, cocoa, coffee with slightly meaty and vegetative nuances |
| Flavor Type: Moldy | |
| moldy, earthy, vegetable, potato, savory, brown, meaty, musty, jammy | |
| Luebke, William tgsc, (2017) | Moldy earthy vegetable potato savory brown meaty |
| Mosciano, Gerard P&F 24, No. 5, 41, (1999) | At 1.00 - 5.00 ppm. Musty, vegetative, savory meaty with a brown jammy fullness in the aftertaste |
| FURANEOL ® METHYLETHER brings along with its typical caramelic character, slight meaty and green nuances which work perfectly in strawberry, crab, orange, forest fruits and banana flavors. | Burnt sugar metallic musty raw potato vegetable and bready notes |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Blackberry , Coffee , Fruit , Fungus , Gooseberry , Grape , Kiwi , Mango , Maple , Pineapple , Raspberry , Strawberry |
| Flavoring purposes | Caramel , Chocolate cocoa , Nut |
Safety Information
Safety information
| Preferred SDS: View | |
| European 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 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. | |
| 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 strawberry furanone methyl ether usage levels up to: | |||
| 0.5000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 19.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.70 (μg/capita/day) | ||
| Structure Class: | II | ||
| 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: | - | 12.00000 | |
| beverages(nonalcoholic): | - | 0.50000 | |
| beverages(alcoholic): | - | 1.00000 | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 10.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | 2.50000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 3.00000 | |
| fruit ices: | - | 3.00000 | |
| gelatins / puddings: | - | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 5.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | 2.50000 | |
| meat products: | - | - | |
| milk products: | - | 2.50000 | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | 2.50000 | |
| 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 220: alpha,beta-Unsaturated ketones and precursors from chemical subgroup 4.4 of FGE.19: 3(2H)-Furanones View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 220, Revision 1 (FGE.220Rev1): alpha,beta-Unsaturated ketones and precursors from chemical subgroup 4.4 of FGE.19: 3(2H)-Furanones View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 220, Revision 2 (FGE.220Rev1): a,ß-Unsaturated ketones and precursors from chemical subgroup 4.4 of FGE.19: 3(2H)-Furanones View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 220 Revision 3 (FGE.220Rev3): Consideration of genotoxic potential for a,ß-unsaturated 3(2H)-Furanones from subgroup 4.4 of FGE.19 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 99 Revision 1 (FGE.99Rev1): Consideration of furanone derivatives evaluated by the JECFA (63rd, 65th and 69th meetings) View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):4077-47-8 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :61325 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 4-methoxy-2,5-dimethylfuran-3-one |
| Chemidplus:0004077478 |