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tonka furanone
Tonka furanone, also known as dehydromenthofurolactone, is a coumarinic-flavored compound used in flavors and fragrances, notably for tropical and tonka bean notes.
General Material Description
Tonka furanone (PubChem CID 3018936), chemically identified as 5,6-dihydro-3,6-dimethyl-2(4H)-benzofuranone, is a lactone compound classified within flavor and fragrance agents. It presents as a colorless to pale liquid with a distinctive coumarinic odour reminiscent of tonka bean, new mown hay, and coconut. This compound's molecular formula is C10H12O2. Synonyms include dehydromenthofurolactone and several benzofuranone-based names reflecting its chemical structure. Tonka furanone is typically sourced synthetically and is valued for imparting tropical, amber, and creamy cocoa-like nuances in flavor and scent applications, linking sensory characteristics with natural tonka bean notes.
Occurrence, Applicability & Potential Uses
Tonka furanone occurs mainly as a synthetic lactone used to mimic or enhance natural tonka bean and coumarin aromas in flavor and fragrance formulations. Its senses evoke elements such as coconut, new mown hay, and tropical fruit profiles. The compound finds applications in products requiring amber, tropical, or creamy notes, including beverages, confectionery, and perfumes. Regarding safety and regulatory frameworks, its use is guided by IFRA (Global) standards, which recommend maximum usage levels of 1.0% in fragrance concentrates to ensure consumer safety. The compound's flavoring use is recognized by FEMA (US) with GRAS status under number 3755, indicating acceptance in flavor applications within regulated limits.
Physico-Chemical Properties Summary
Tonka furanone exhibits physical properties pertinent to its performance in formulations: it is a liquid with a specific gravity ranging between 1.09 and 1.096 at 25°C and a refractive index from 1.542 to 1.548 at 20°C. The boiling point is approximately 264 to 266°C at a reduced pressure of 10 mm Hg, indicating a relatively low volatility under ambient conditions. Its estimated logP of about 1.9 suggests moderate lipophilicity, enhancing solubility in alcoholic solvents and slight solubility in water at 1718 mg/L at 25°C. The flash point is 136°C (278°F), reflecting a moderately high resistance to ignition. These attributes influence its stability, handling, and blending in both aqueous and nonaqueous matrices.
FAQ
What is tonka furanone and what are its key characteristics?
Tonka furanone, also known by its chemical name 5,6-dihydro-3,6-dimethyl-2(4H)-benzofuranone or dehydromenthofurolactone, is a lactone compound used extensively in flavor and fragrance compositions. It is characterized by a coumarinic aroma reminiscent of tonka bean, coconut, and new mown hay. The compound is synthetic and is valued for imparting tropical and amber olfactory notes. Chemically, it has the molecular formula C10H12O2 and possesses moderate lipophilicity which allows it to function effectively in various formulations.
How and where is tonka furanone typically used in the industry?
Tonka furanone is predominantly utilized as a flavoring and fragrance agent in the food and cosmetic industries. It is applied to impart tropical, amber, and tonka bean-like notes in products such as beverages, confectionery items, and perfumes. Due to its sensory profile and chemical stability, it serves as an aromatic enhancer in formulations requiring creamy, coumarinic nuances. The compound is manufactured synthetically and blended carefully within established concentration limits to comply with safety and regulatory guidelines.
What regulations govern the use and safety of tonka furanone?
The use of tonka furanone in fragrances is regulated by the International Fragrance Association (IFRA) under global guidelines, recommending maximum levels of 1.0% concentration in fragrance concentrates to ensure safe consumer exposure. In flavors, the Flavor and Extract Manufacturers Association (FEMA) in the US has assigned it the GRAS status with FEMA number 3755, qualifying it for use within specified limits. Toxicological evaluations conducted by authorities such as the European Food Safety Authority (EFSA) have been reviewed without indicating significant hazards, and no formal OSHA hazard classifications apply. Usage must adhere to these standards to maintain regulatory compliance and safety.
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 |
| HMDB (The Human Metabolome Database): | HMDB37174 |
| FooDB: | FDB016170 |
| Export Tariff Code: | 2932.19.0000 |
| 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 | tonka furanone |
| Trivial Name | 5,6-Dihydro-3,6-dimethyl-2(4H)-benzofuranone |
| Short Description | dehydromenthofurolactone |
| Formula | C10 H12 O2 |
| CAS Number | 80417-97-6 |
| FEMA Number | 3755 |
| Flavis Number | 10.034 |
| ECHA Number | 279-462-2 |
| FDA UNII | HQN74S1YWS |
| Nikkaji Number | J320.270D |
| xLogP3-AA | 1.90 (est) |
| NMR Predictor | External link |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 164.20404052734 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.07 to 9.12 |
| Refractive Index | 1.542 to 1.548 @ 20 °C |
| Boiling Point | 264 to 266°C @ 10 mm Hg |
| Vapor Pressure | 0.000154 mmHg @ 25 °C |
| Flash Point TCC Value | 136.67 °C TCC |
| logP (o/w) | 1.927 est |
| Solubility | |
| alcohol | Yes |
| water, slightly | Yes |
| water, 1718 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Coumarinic | |
| tonka, hay, coumarinic, coconut | |
| General comment | At 100.00 %. tonka hay coumarin coconut |
Potential Uses
| Applications | |
| Odor purposes | Amber , Coconut , Hay new mown hay , Pina colada , Tonka bean |
| Flavoring purposes | Tropical |
Safety Information
Safety information
| 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 tonka furanone usage levels up to: | |||
| 1.0000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.01 (μg/capita/day) | ||
| Structure Class: | III | ||
| 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: 15 | |||
| Click here to view publication 15 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | - | |
| beverages(nonalcoholic): | - | 1.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | 20.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | 5.00000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | 2.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 5.00000 | |
| 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 217: alpha,beta-Unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: Lactones[1] View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 217, Revision 1 (FGE.217Rev1). Consideration of genotoxic potential for a,ß-unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: Lactones View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 217 Revision 2 (FGE.217Rev2), consideration of genotoxic potential for a,ß-unsaturated ketones and precursors from chemical subgroup 4.1 of FGE.19: lactones View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :3018936 |
| National Institute of Allergy and Infectious Diseases:Data |
| 3,6-dimethyl-5,6-dihydro-4H-1-benzofuran-2-one |
| Chemidplus:0080417976 |