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2-isobutyl thiazole
2-isobutyl thiazole is a heterocyclic compound known for its green, tomato leaf odor and flavor, utilized primarily in flavor and fragrance applications.
General Material Description
2-isobutyl thiazole is a sulfur-containing heterocyclic organic compound with the molecular formula C7H11NS. It appears as a colorless to pale yellow liquid and is recognized for its distinctive green, earthy odor with tomato leaf and vegetable nuances. The compound is also known by several synonyms including 2-(2-methylpropyl)-1,3-thiazole and tomato leaf thiazole. According to PubChem, it is classified within heterocyclic compounds containing nitrogen and sulfur. This material is typically isolated from natural sources like cantaloupe fruit and tomato or synthesized for use in flavor and fragrance formulations.
Occurrence, Applicability & Potential Uses
2-isobutyl thiazole naturally occurs in cantaloupe fruit and tomato, contributing to their characteristic aromas. It is applied predominantly in the flavor and fragrance industry, where it imparts green, fresh, and tomato-like notes. The compound holds essential value for enhancing tomato flavors in food products such as ketchup and condiments. Additionally, it is employed as a perfuming agent in cosmetics. Usage levels are guided by standards including FEMA (US), where it is recognized as a flavoring substance with specific concentration limits to ensure quality and safety in formulations.
Physico-Chemical Properties Summary
This compound exhibits moderate volatility with a vapor pressure of approximately 1.091 mmHg at 25°C and a boiling range from 174 to 180°C at atmospheric pressure. It has a refractive index between 1.494 and 1.498 at 20°C and a specific gravity close to 1.0 at 20-25°C, indicating near water-like density. The estimated logP value of 1.715 suggests moderate lipophilicity, which affects its solubility and interaction in both aqueous and lipid environments. It is partially soluble in alcohol and exhibits limited water solubility (~255 mg/L at 25°C estimated). The flash point is about 57°C (135°F), implying a moderate flammability risk. The compound is stable in most media, factors important for its use in durable flavor and fragrance products.
FAQ
What is 2-isobutyl thiazole and what are its primary sensory characteristics?
2-isobutyl thiazole is a sulfur-containing heterocyclic compound notable for its green, vegetable, and tomato leaf aroma and flavor. It exhibits strong green odor notes with earthy and musty nuances, often described as tomato-like. This sensory profile makes it valuable in flavor and fragrance formulations to impart fresh, green, and natural vegetable or fruit impressions.
Where is 2-isobutyl thiazole found naturally and how is it typically used?
This compound naturally occurs in various fruits such as cantaloupe and tomato, contributing to their characteristic aroma profiles. It is widely used in flavoring to enhance tomato flavors in food products like condiments and juices, generally at concentrations between 0.02 and 1.0 ppm. Additionally, it serves as a perfuming agent in cosmetics due to its distinctive green and green-leaf scent qualities.
What regulations and safety evaluations apply to 2-isobutyl thiazole in flavor and fragrance applications?
2-isobutyl thiazole is evaluated under regulatory frameworks such as FEMA (US) and REACH (EU). Recognized as a flavoring substance, its usage limits are recommended up to 0.08% in fragrance concentrates according to IFRA guidelines. Safety assessments by organizations including EFSA have examined its toxicological profile, supporting its controlled use in food and cosmetic products. It is classified as an irritant under European regulations, and appropriate handling precautions are advised.
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
| 2-(2-methylpropyl)-1,3-thiazole | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 18640-74-9 |
| Pubchem (cid): | 62725 |
| Pubchem (sid): | 135021306 |
| Flavornet: | 18640-74-9 |
| Pherobase: | View |
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 |
| CHEMBL: | View |
| HMDB (The Human Metabolome Database): | HMDB31862 |
| FooDB: | FDB008546 |
| YMDB (Yeast Metabolome Database): | YMDB01585 |
| Export Tariff Code: | 2934.10.0090 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2-isobutyl thiazole |
| Trivial Name | 2-Isobutylthiazole |
| Short Description | 2-isobutylthiazole |
| Formula | C7 H11 N S |
| CAS Number | 18640-74-9 |
| FEMA Number | 3134 |
| Flavis Number | 15.013 |
| ECHA Number | 242-470-1 |
| FDA UNII | 7N03TDY75D |
| Nikkaji Number | J45.613F |
| MDL | MFCD00005334 |
| COE Number | 11618 |
| xLogP3-AA | 2.60 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1034 2-isobutylthiazole |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 141.23666381836 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 8.279 to 8.282 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.331 to 8.364 |
| Refractive Index | 1.494 to 1.498 @ 20 °C |
| Refractive Index | 1.49 to 1.499 @ 20 °C |
| Boiling Point | 174 to 180°C @ 760 mm Hg |
| Vapor Pressure | 1.091 mmHg @ 25 °C |
| Vapor Density | 4.8 |
| Flash Point TCC Value | 57.22 °C TCC |
| logP (o/w) | 1.715 est |
| Solubility | |
| alcohol | Yes |
| water, 255.2 mg/L @ 25 °C (est) | Yes |
| water | No |
| Stability | |
| stable in most media | Unspecified |
Organoleptic Properties
| Odor Type: Green | |
| green, wasabi, privet, tomato leaf, earthy, vegetable, metallic, musty, waxy | |
| Odor strength | high , recommend smelling in a 0.10 % solution or less |
| Substantivity | > 1 hour(s) at 100.00 % |
| Luebke, William tgsc, (2009) | At 1.00 % in dipropylene glycol. green wasabi privet tomato leaf earthy vegetable metallic |
| Mosciano, Gerard P&F 17, No. 4, 33, (1992) | Green, vegetable, musty with a waxy nuance |
| Flavor Type: Green | |
| green, vegetable, tomato, raw, musty | |
| Mosciano, Gerard P&F 17, No. 4, 33, (1992) | At 2.00 ppm. Green, vegetable, tomato-like with raw musty nuances |
| Effective in enhancing tomato juice at 25-50 ppb. Useful for enhancing Tomato flavor of condiments (e.g., Ketchup). This compound is essential to the flavor of Tomato. Normal use levels in finished consumer product: 0.02-1.0 ppm. | Green tomato |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Apricot , Earth , Floral , Fungus , Green , Musk , Peach , Tomato leaf |
| Flavoring purposes | Tomato , Vegetable |
| Other purposes | Leaf , Vine |
| Cosmetic purposes | Perfuming agents |
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 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: | |
| 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-isobutyl thiazole usage levels up to: | |||
| 0.0800 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 3.00 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.40 (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: 4 | |||
| Click here to view publication 4 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 1.00000 | |
| beverages(nonalcoholic): | - | 1.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 1.00000 | |
| fruit ices: | - | 1.00000 | |
| gelatins / puddings: | - | 1.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | 1.00000 | |
| hard candy: | - | 1.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 1.00000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | 1.00000 | |
| 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 21: Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29. Miscellaneous substances from chemical group 30. (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) View page or View pdf |
| Flavouring Group Evaluation 76, (FGE.76)[1] - Consideration of sulphur-containing heterocyclic compounds evaluated by JECFA (59th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29, miscellaneous substances from chemical group 30 evaluated by EFSA in FGE.21 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food View page or View pdf |
| Flavouring Group Evaluation 21, Revision 1 (FGE.21Rev1): Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29 Miscellaneous substances from chemical group 30 View page or View pdf |
| Scientific Opinion on the safety and efficacy of thiazoles, thiophene, thiazoline and thienyl derivatives (chemical group 29): 3-acetyl-2,5-dimethylthiophene when used as a flavouring for all animal species View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 76, Revision 1 (FGE.76Rev1): Consideration of sulphur-containing heterocyclic compounds evaluated by JECFA (59th meeting) structurally related to thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29 and miscellaneous substances from chemical group 30 evaluated by EFSA in FGE.21Rev3 View page or View pdf |
| Safety and efficacy of thiazoles, thiophene and thiazoline belonging to chemical group 29 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 Substance Registry Services (TSCA):18640-74-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :62725 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 1993 |
| WGK Germany:3 |
| 2-(2-methylpropyl)-1,3-thiazole |
| Chemidplus:0018640749 |
| RTECS:XJ5103412 for cas# 18640-74-9 |