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2,4,5-trimethyl oxazole
2,4,5-trimethyl oxazole is an aroma compound with nutty and burnt flavor notes used in flavor and fragrance applications.
General Material Description
2,4,5-trimethyl oxazole is a heterocyclic aromatic compound with the molecular formula C6H9NO. It appears as a colorless liquid featuring sensory notes described as nutty and burnt, contributing a characteristic aroma to various foods and fragrances. Synonyms include trimethyloxazole and 2,4,5-trimethyl-1,3-oxazole, among others. This compound has been identified in multiple heated and processed foods such as beef, chicken, coffee, and cocoa, indicating its formation during cooking or fermentation processes. It is typically sourced or synthesized for use as a flavor and fragrance agent. An authoritative chemical database entry can be found under PubChem CID 30215.
Occurrence, Applicability & Potential Uses
2,4,5-trimethyl oxazole naturally occurs in the aromas of heated meats including beef, chicken, and pork, as well as in brandy, cocoa, coffee, and cooked egg products. It is also detected in fermented or autolyzed yeast and in some vegetable components like kohlrabi stem. Its presence in these foods suggests a role in imparting desirable nutty, roasted, and burnt notes typical of cooking and fermentation reactions. This compound is employed as a flavor and fragrance agent in food and beverage formulation, especially to enhance meat-like, chocolate, coffee, and pork flavors. Regulatory assessments such as FEMA (US) and JECFA (FAO/WHO) evaluate its safety and permissible usage levels in food applications.
Physico-Chemical Properties Summary
2,4,5-trimethyl oxazole has a moderate boiling point between 133 and 134 °C at standard atmospheric pressure, indicating typical volatility for aroma compounds used in flavoring. Its estimated logP value of approximately 1.2 reflects moderate lipophilicity, facilitating partitioning into oil and fat phases in formulations. The compound’s specific gravity ranges from 0.956 to 0.964 at 25 °C, and its refractive index lies between 1.438 and 1.446 at 20 °C, useful data for quality control and identification. Its vapor density exceeds air, supporting its dispersion in vapor form. Solubility characteristics include partial solubility in water (estimated 2801 mg/L at 25 °C) and good solubility in alcohols, influencing its behavior in beverages and other aqueous-alcoholic systems. The flash point is 92 °F, marking a moderate flammability hazard to consider during handling and processing.
FAQ
What is 2,4,5-trimethyl oxazole and what are its sensory characteristics?
2,4,5-trimethyl oxazole is an aromatic heterocyclic compound used primarily as a flavor and fragrance agent. It imparts nutty and burnt sensory notes, often described as reminiscent of roasted nuts, hazelnut, and smoky or boiled impressions. These characteristics contribute to the aroma profiles of cooked meats, chocolate, coffee, and similar food products. Its odor strength is considered medium, with substantivity under an hour at pure concentrations.
Where is 2,4,5-trimethyl oxazole found naturally and how is it applied in industry?
This compound naturally arises in heated and cooked foods such as beef, pork, chicken, coffee, cocoa, and cooked eggs due to thermal and fermentation processes. It also appears in brandy and yeast autolysates. Industrially, it is synthesized and incorporated as a flavor and fragrance ingredient to reproduce or enhance these sensory profiles in food and beverage formulations. Regulatory bodies like FEMA and JECFA define usage levels to ensure consumer safety.
What regulations and safety considerations apply to 2,4,5-trimethyl oxazole in food flavoring?
2,4,5-trimethyl oxazole is evaluated by FEMA (US) with number 4394 and JECFA (FAO/WHO) with number 1553 for flavoring uses. Usage limits are established to prevent toxicity, with FEMA providing general recognized as safe (GRAS) status and specifying maximum application levels across food categories. Safety assessments note it as flammable and an irritant to eyes, skin, and respiratory system under concentrated exposure. Handling guidelines recommend protective measures to limit irritation risk, and it is subject to chemical safety regulations including labeling and exposure controls.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| NCBI | Start search |
Literature & References
| 2,4,5-trimethyl-1,3-oxazole | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 20662-84-4 |
| Pubchem (cid): | 30215 |
| Pubchem (sid): | 134994007 |
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): | HMDB40148 |
| FooDB: | FDB019845 |
| Export Tariff Code: | 2934.99.4400 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2,4,5-trimethyl oxazole |
| Trivial Name | Trimethyloxazole |
| Short Description | 2,4,5-trimethyloxazole |
| Formula | C6 H9 N O |
| CAS Number | 20662-84-4 |
| FEMA Number | 4394 |
| Flavis Number | 13.169 |
| ECHA Number | 243-952-4 |
| FDA UNII | B04PF51WXI |
| Nikkaji Number | J40.167F |
| MDL | MFCD00005308 |
| COE Number | 11424 |
| xLogP3-AA | 1.50 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1553 trimethyloxazole |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 20662-84-4 ; TRIMETHYLOXAZOLE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 111.14392852783 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.955 to 8.021 |
| Refractive Index | 1.438 to 1.446 @ 20 °C |
| Boiling Point | 133 to 134°C @ 760 mm Hg |
| Vapor Pressure | 10.394 mmHg @ 25 °C |
| Vapor Density | 3.8 |
| Flash Point TCC Value | 33.33 °C TCC |
| logP (o/w) | 1.206 est |
| Solubility | |
| alcohol | Yes |
| water, 2801 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Nutty | |
| nutty, nut skin, roasted, wasabi, shellfish, mustard, vegetable | |
| Odor strength | medium , recommend smelling in a 10.00 % solution or less |
| Substantivity | < 1 hour(s) at 100.00 % |
| Luebke, William tgsc, (2008) | At 100.00 %. nutty nut skin roasted wasabi shellfish mustard vegetable |
| Flavor Type: Burnt | |
| burnt, nutty, hazelnut, oily, nut skin, potato, earthy, mushroom | |
| Luebke, William tgsc, (2008) | Burnt nutty hazelnut oily nut skin potato earthy mushroom |
| Used in meat flavours to give a boiled note. | Earthy potato-like and mushroom |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Flavoring purposes | Beef , Chocolate cocoa , Coffee , Pork |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 10 - Flammable. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. 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 37/39 - Wear suitable 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: | |
| 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 2,4,5-trimethyl oxazole usage levels up to: | |||
| 0.3000 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 3.70 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 1.00 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 96 (μg/person/day) | ||
| Threshold of Concern: | 540 (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: 23 | |||
| Click here to view publication 23 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.40000 | 2.00000 | |
| beverages(nonalcoholic): | 0.20000 | 1.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | 0.20000 | 1.00000 | |
| cheese: | 0.40000 | 2.00000 | |
| chewing gum: | - | - | |
| condiments / relishes: | 0.20000 | 1.00000 | |
| confectionery froastings: | 0.40000 | 2.00000 | |
| egg products: | - | - | |
| fats / oils: | 0.20000 | 1.00000 | |
| fish products: | 0.10000 | 0.40000 | |
| frozen dairy: | 0.40000 | 2.00000 | |
| fruit ices: | 0.40000 | 2.00000 | |
| gelatins / puddings: | 1.00000 | 5.00000 | |
| granulated sugar: | - | - | |
| gravies: | 1.00000 | 5.00000 | |
| hard candy: | - | - | |
| imitation dairy: | 0.40000 | 2.00000 | |
| instant coffee / tea: | - | - | |
| jams / jellies: | 1.00000 | 5.00000 | |
| meat products: | 0.10000 | 0.40000 | |
| milk products: | 0.40000 | 2.00000 | |
| nut products: | - | - | |
| other grains: | 0.20000 | 1.00000 | |
| poultry: | 0.10000 | 0.40000 | |
| processed fruits: | 0.30000 | 1.50000 | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 0.20000 | 1.00000 | |
| snack foods: | 0.20000 | 1.00000 | |
| soft candy: | - | - | |
| soups: | 0.20000 | 1.00000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | 0.20000 | 1.00000 | |
| 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): | 0.40000 | 2.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.20000 | 1.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.40000 | 2.00000 | |
| Processed fruit (04.1): | 0.30000 | 1.50000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 0.40000 | 2.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 0.20000 | 1.00000 | |
| Bakery wares (07.0): | 0.40000 | 2.00000 | |
| Meat and meat products, including poultry and game (08.0): | 0.10000 | 0.40000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.10000 | 0.40000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.20000 | 1.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 0.40000 | 2.00000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | - | - | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 0.40000 | 2.00000 | |
| Ready-to-eat savouries (15.0): | 1.00000 | 5.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.20000 | 1.00000 | |
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): |
| Flavouring Group Evaluation 85: Consideration of miscellaneous nitrogen-containing substances evaluated by JECFA (65th meeting)[1] - Scientific Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Safety and efficacy of pyridine and pyrrole derivatives belonging to chemical group 28 when used as flavourings for all animal species 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 :30215 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 1993 |
| WGK Germany:2 |
| 2,4,5-trimethyl-1,3-oxazole |
| Chemidplus:0020662844 |