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difurfuryl ether
Difurfuryl ether is a furan derivative used in flavorings, especially imparting coffee and nut aromas.
General Material Description
Difurfuryl ether is an organic compound classified as a furan derivative with the molecular formula C10H10O3. It appears as a clear liquid and is recognized chemically as 2,2'-[oxybis(methylene)]bisfuran. This compound features two furan rings linked via an ether bridge, which contributes to its characteristic aromatic properties. Difurfuryl ether is noted for its coffee and nut sensory notes and is included in flavoring applications to impart such aromas. The substance is referenced under multiple synonyms, highlighting its structural components, and is indexed in public chemical databases such as PubChem. It can be sourced or identified in natural extracts such as roasted chicory root oil and coffee, from which its flavor characteristics are derived for industrial use.
Occurrence, Applicability & Potential Uses
Difurfuryl ether naturally occurs in roasted chicory root oil at low concentrations (~0.028%) and is also identified in coffee. Its main application is as a flavoring agent, where it contributes distinctive coffee-like and nutty aromatic notes. The compound is utilized in the flavor industry to create or enhance coffee and nut flavors in various products. According to FEMA (US) standards, difurfuryl ether is registered under FEMA number 3337, and it is approved for flavor use within specified limits. This regulatory framework ensures safe application levels in food flavoring formulations, reflecting its acceptance and utility in flavor creation.
Physico-Chemical Properties Summary
Difurfuryl ether exhibits physicochemical traits that influence its flavoring application and formulation behavior. It has a molecular weight of approximately 178.19 g/mol and displays moderate lipophilicity with an estimated log P around 1.8. Specific gravity ranges from 1.506 to 1.512 at 25 °C, indicating a density slightly higher than water. Its refractive index at 20 °C lies between 1.138 and 1.144. The boiling point is measured as 88 to 89 °C at reduced pressure (1 mm Hg), reflecting volatility relevant for flavor release. The flash point is approximately 106 °C (222 °F), signifying its flammability hazard class. Difurfuryl ether has moderate water solubility (~711 mg/L at 25 °C) and dissolves well in alcohol solvents, pertinent for formulation in emulsions or extracts. These properties dictate handling, storage, and blending considerations in flavor manufacturing.
FAQ
What is difurfuryl ether and what are its primary characteristics?
Difurfuryl ether is an organic compound consisting of two furan rings connected by an ether oxygen and methylene groups, giving it the formula C10H10O3. It is known for imparting coffee-like and nutty aromas and flavors, making it valuable in flavor applications. The compound appears as a clear liquid and is chemically identified by synonyms like 2,2'-[oxybis(methylene)]bisfuran. It is indexed in chemical databases including PubChem with the CID 263034.
Where is difurfuryl ether found naturally, and how is it used in industry?
Difurfuryl ether is naturally found in roasted chicory root oil and coffee, contributing to their characteristic aromas. In industry, it is used primarily as a flavoring agent to provide coffee and nut-like sensory notes in various food products. Its use is regulated, and it has assigned identifiers such as FEMA number 3337, ensuring controlled usage in compliance with flavor safety guidelines.
What safety and regulatory standards govern the use of difurfuryl ether in flavorings?
The use of difurfuryl ether as a flavoring compound is overseen by regulatory bodies such as FEMA (US), which has assigned it the number 3337 and classifies it within flavoring substances generally recognized as safe when used within specified limits. Safety data indicate it can be an irritant to eyes, skin, and respiratory systems, and appropriate precautions are recommended during handling. Its maximum recommended use levels are defined to minimize exposure, and it is not authorized for fragrance uses. Comprehensive safety evaluations by organizations like EFSA have reviewed its toxicological profile for safe application in foods.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 2-(furan-2-ylmethoxymethyl)furan | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 4437-22-3 |
| Pubchem (cid): | 263034 |
| Pubchem (sid): | 135263851 |
| Publications by Info | |
| substances containing furan substitution | |
| Publications by US Patents | |
| 3,940,502 - Flavoring agent | |
| Furfurylthioacetone | |
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): | HMDB33248 |
| FooDB: | FDB011267 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | 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 | difurfuryl ether |
| Trivial Name | Difurfuryl ether |
| Short Description | 2,2'-[oxybis(methylene)]bisfuran |
| Formula | C10 H10 O3 |
| CAS Number | 4437-22-3 |
| Deleted CAS Number | 1801783-78-7 |
| FEMA Number | 3337 |
| Flavis Number | 13.061 |
| FDA UNII | 55L57OC81G |
| Nikkaji Number | J102.641K |
| Beilstein Number | 0156726 |
| COE Number | 10930 |
| xLogP3-AA | 1.30 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1522 difurfuryl ether |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 4437-22-3 ; DIFURFURYL ETHER |
| Synonyms |
|
Suppliers
| BOC Sciences | Penta International |
| United International | WholeChem |
| Penta International Corporation | Taytonn ASCC |
| Qingdao Free Trade Zone United International Co Ltd |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 178.18730163574 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 12.531 to 12.581 |
| Refractive Index | 1.138 to 1.144 @ 20 °C |
| Boiling Point | 88 to 89°C @ 1 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 0.109 mmHg @ 25 °C |
| Flash Point TCC Value | 105.56 °C TCC |
| logP (o/w) | 1.797 est |
| Solubility | |
| alcohol | Yes |
| water, 711.3 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Coffee | |
| coffee, nutty, earthy | |
| General comment | At 0.10 % in propylene glycol. coffee nutty earthy |
| Flavor Type: Coffee | |
| coffee, mushroom | |
| General comment | Coffee mushroom-like |
Occurrences
| (data available) |
Safety Information
Safety information
| 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 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 36/37/39 - Wear suitable clothing, gloves and eye/face protection. | |
| 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 210 mg/kg GASTROINTESTINAL: ULCERATION OR BLEEDING FROM DUODENUM GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 93, 1990. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for difurfuryl ether usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.12 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.09 (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: 6 | |||
| Click here to view publication 6 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 1.00000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 1.00000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 1.00000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | 1.00000 | |
| 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 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 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 |
| Statement on List of Representative Substances for Testing. The current Statement lays down a list of substances in sub-groups with representative substances for which additional data are required prior to their evaluation through the Procedure (Regulation (EC) No 1565/2000). View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 67 Revision 2 (FGE.67Rev2): Consideration of 28 furan-substituted compounds evaluated by JECFA at the 55th, 65th and 69th meetings (JECFA, 2001, 2006a, 2009b) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 67, Revision 3 (FGE.67Rev3): consideration of 23 furan-substituted compounds evaluated by JECFA at the 55th, 65th, 69th and 86th meetings View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):4437-22-3 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :263034 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2-(furan-2-ylmethoxymethyl)furan |
| Chemidplus:0004437223 |