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2-acetyl-2-thiazoline
2-acetyl-2-thiazoline is a sulfur-containing flavor compound known for its nutty, corn chip aroma used in food flavoring applications.
General Material Description
2-acetyl-2-thiazoline, chemically known as 1-(4,5-dihydrothiazol-2-yl)ethanone, is a heterocyclic sulfur compound with the molecular formula C5H7NOS. It appears as a colorless to pale yellow liquid notable for its distinctive corn chip and toasted nut aroma. This compound is structurally related to thiazolines and possesses an aromatic ketone functional group. Well-documented in flavor chemistry, it is naturally found in foods such as roasted corn and cooked meats and is also produced via Maillard reaction pathways. The compound's PubChem entry (CID 169110) confirms its chemical identity and properties. Sourced primarily through synthetic routes for industrial flavor use, 2-acetyl-2-thiazoline is valued for its characteristic roasted, nutty, and baked bread notes.
Occurrence, Applicability & Potential Uses
2-acetyl-2-thiazoline is present biologically in cooked beef, chicken, coffee aroma, and sweet corn, contributing characteristic nutty, roasted, and corn chip notes. Its presence is often a result of thermal processing or Maillard-type reactions in protein- and sugar-rich foods. This compound finds application as a flavoring agent in various culinary products, from snack foods to baked goods, adding desirable toasted and savory characteristics. Regulatory evaluations such as FEMA (US) recognize it as FEMA GRAS (Generally Recognized as Safe) for flavor use. It is utilized to enhance almond, hazelnut, coffee, meat, and bread flavors, playing a functional role in complex flavor systems offering roasted and toasted impressions.
Physico-Chemical Properties Summary
2-acetyl-2-thiazoline exhibits physical and chemical properties that influence its handling and use in flavor formulations. It is a liquid at room temperature with a specific gravity of approximately 1.16 to 1.17 at 25 °C and a refractive index ranging from 1.5274 to 1.5284 at 20 °C. The compound boils at about 222 to 223 °C under atmospheric pressure and has a low vapor pressure of 0.0942 mmHg at 25 °C, indicating low volatility under ambient conditions. Its estimated logP value of -0.89 suggests moderate polarity with some hydrophilic character, consistent with partial water solubility below 12 g/L. The flash point is measured at 198 °F (approximately 92 °C), requiring standard precautions during storage and handling. Stable under proper storage conditions, it retains quality for at least 24 months if stored sealed in a cool, dry place protected from light and heat. Solubility in alcohols facilitates formulation into flavor blends.
FAQ
What is 2-acetyl-2-thiazoline and what are its key flavor characteristics?
2-acetyl-2-thiazoline is a sulfur-containing heterocyclic compound known for imparting nutty, toasted corn chip aromas. It features prominently in the flavor profile of roasted corn, baked bread, and cooked meats. The compound is valued for delivering roasted, toasted, and roasted nut notes that enhance savory and snack food flavors.
Where does 2-acetyl-2-thiazoline naturally occur and how is it used in flavoring products?
This compound naturally occurs in thermally processed foods such as beef, chicken, coffee aromas, and sweet corn. It forms via Maillard reactions during cooking. In the flavor industry, 2-acetyl-2-thiazoline is used as a flavoring agent to add roasted, nutty, and baked notes to products including snack foods, baked goods, and savory items. Its characteristic corn chip and toasted flavors contribute to complex food flavor profiles.
What regulatory standards govern the use of 2-acetyl-2-thiazoline and how can it be safely stored?
2-acetyl-2-thiazoline is recognized by FEMA (US) as a generally recognized as safe (GRAS) flavoring substance within defined use levels. It is included in flavoring evaluations by entities such as EFSA (European Food Safety Authority). For safe storage, it should be kept in tightly sealed containers, away from heat and light, in a cool, dry location. The compound has a shelf life of at least 24 months under proper conditions. No significant hazard classifications have been identified in OSHA HCS standards.
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 |
Literature & References
| 1-(4,5-dihydro-1,3-thiazol-2-yl)ethanone | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 29926-41-8 |
| Pubchem (cid): | 169110 |
| Pubchem (sid): | 135122927 |
| Flavornet: | 29926-41-8 |
| Pherobase: | View |
| Publications by Perfumer & Flavorist | |
| Organoleptic Characteristics of Flavor Materials | |
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): | HMDB33561 |
| FooDB: | FDB011630 |
| YMDB (Yeast Metabolome Database): | YMDB01448 |
| Export Tariff Code: | 2934 10 0090 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2-acetyl-2-thiazoline |
| Trivial Name | 2-Acetyl-2-thiazoline |
| Short Description | 1-(4,5-dihydrothiazol-2-yl)ethanone |
| Formula | C5 H7 N O S |
| CAS Number | 29926-41-8 |
| FEMA Number | 3817 |
| Flavis Number | 15.01 |
| FDA UNII | TI3K1Q5Y1T |
| Nikkaji Number | J668.744J |
| MDL | MFCD00209496 |
| COE Number | 2335 |
| xLogP3-AA | 0.20 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1759 2-acetyl-2-thiazoline |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 29926-41-8 ; 2-ACETYL-2-THIAZOLINE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 129.18199157715 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.652 to 9.736 |
| Refractive Index | 1.5274 to 1.5284 @ 20 °C |
| Boiling Point | 222 to 223°C @ 760 mm Hg |
| Vapor Pressure | 0.0942 mmHg @ 25 °C |
| Flash Point TCC Value | 92.22 °C TCC |
| logP (o/w) | -0.89 |
| Shelf life | 24 months (or longer if stored properly.) |
| Storage notes | Store in cool, dry place in tightly sealed containers, protected from heat and light. |
| Solubility | |
| alcohol | Yes |
| water, 1.127e+004 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Corn chip | |
| corn chip, taco, potato chip, toasted, bready, nutty, onion green onion, chicken, grain toasted grain, roasted, herbal, grassy | |
| Luebke, William tgsc, (1993) | At 0.10 % in propylene glycol. corn chip taco potato chip toasted bread nutty |
| Mosciano, Gerard P&F 24, No. 6, 10, (1999) | At 1.00 % in ethyl alcohol. Corn chips, green onion, crispy chicken skin, toasted grain with a nutty background, roasted nutty dry out, herbal and grassy |
| Flavor Type: Corn chip | |
| corn chip, popcorn, roasted, grain toasted grain, salty | |
| Mosciano, Gerard P&F 24, No. 6, 10, (1999) | At 1.00 - 5.00 ppm. Taco chips, slightly popcorn, toasted and roasted grain, salty impression |
| Useful in: brown nuts, brown cereals, brown others, savory meat. | Baked bread crust, roasted |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Acorn , Bread baked bread , Gingerbread , Tobacco |
| Flavoring purposes | Almond toasted almond , Barley , Bread , Bread crust , Bread rye bread , Bread wheat bread , Bread white bread , Cake , Cashew , Chocolate cocoa , Coffee , Corn , Corn chip , Corn sweet corn , Filbert , Graham cracker , Hazelnut , Meat , Nut , Nut roasted nut , Peanut , Pecan , Pistachio , Pizza , Popcorn , Seafood , Sesame , Taco |
| Other purposes | Toasted , Wheat |
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: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 2-acetyl-2-thiazoline usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.51 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | ND (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 810 (μg/person/day) | ||
| Threshold of Concern: | 540 (μg/person/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: 18 | |||
| Click here to view publication 18 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.02000 | 0.20000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | 0.01000 | 0.10000 | |
| cheese: | - | - | |
| chewing gum: | 0.05000 | 0.50000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | 0.01000 | 0.10000 | |
| egg products: | - | - | |
| fats / oils: | 0.01000 | 0.10000 | |
| fish products: | 0.02000 | 0.20000 | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | 0.02000 | 0.20000 | |
| hard candy: | 0.01000 | 0.10000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 0.02000 | 0.20000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | 0.01000 | 0.10000 | |
| poultry: | 0.02000 | 0.20000 | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | 0.05000 | 0.50000 | |
| soft candy: | 0.01000 | 0.10000 | |
| soups: | 0.02000 | 0.20000 | |
| sugar substitutes: | - | - | |
| sweet sauces: | - | - | |
| 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): | 0.20000 | 1.00000 | |
| 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 93 (FGE.93): Consideration of sulphur heterocyclic evaluated by JECFA (68th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl evaluated by EFSA in FGE.21Rev1 (2009) 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 21, Revision 4 (FGE.21Rev4): Thiazoles, thiophenes, thiazoline and thienyl derivatives from chemical groups 29 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 93, Revision 1 (FGE.93Rev1): Consideration of sulphur containing heterocyclic compounds evaluated by JECFA (68th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl derivatives evaluated by EFSA in FGE.21Rev3 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 :169110 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 2811 |
| WGK Germany:3 |
| 1-(4,5-dihydro-1,3-thiazol-2-yl)ethanone |
| Chemidplus:0029926418 |