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2-hexyl thiophene
2-Hexyl thiophene is a sulfur-containing heterocyclic compound used primarily as a flavoring agent with a floral, fruity, and gassy aroma profile.
General Material Description
2-Hexyl thiophene is a sulfur-containing heterocyclic organic compound with the molecular formula C10H16S. It is characterized by a distinct sulfurous odor with floral, fruity, gassy, green, and meaty nuances when diluted at 0.10% concentration in dipropylene glycol. The compound has several synonyms, including 2-hexylthiophene, 2-N-hexylthiophene, and α-hexylthiophene, reflecting its structural variants and naming conventions. As a heterocycle, it belongs to the class of thiophenes and is linked in controlled-vocabulary databases such as PubChem for chemical identification and reference. Typically, 2-hexyl thiophene is sourced synthetically for use in flavoring applications, taking advantage of its characteristic sensory properties that contribute to food flavor profiles where sulfurous and green notes are desirable.
Occurrence, Applicability & Potential Uses
2-Hexyl thiophene occurs naturally in various cooked and roasted meats such as beef, lamb, turkey, and guinea hen, as well as in cranberry fruits and mushrooms. Its presence contributes to the complex aroma profiles of these foods, often imparting sulfurous, green, and meaty notes. This compound is primarily used as a flavoring agent, enhancing flavors in chicken, cranberry, cucumber, green vegetable notes, and seafood products. Regulatory assessments such as IFRA (Global) and FEMA (US) have evaluated this heterocyclic sulfur-containing compound for use levels in foods, confirming its suitability within defined concentration limits. Its application ranges from processed fruits and vegetables to meat and poultry products, where subtle sulfurous flavors are needed to replicate or intensify natural characteristics.
Physico-Chemical Properties Summary
The physicochemical attributes of 2-hexyl thiophene significantly influence its use in flavor formulations. With a molecular weight of approximately 168.3 g/mol and a boiling point ranging from 229 to 230 °C at atmospheric pressure, it is relatively stable under typical processing conditions. Its specific gravity at 20 °C varies between 0.93 and 0.938, and its refractive index lies between 1.492 and 1.498 at the same temperature, indicating moderate density and optical properties. The compound exhibits a vapor pressure of 0.155 mmHg at 25 °C and an estimated log P value of 4.79, reflecting high lipophilicity, which affects its solubility and distribution in formulations. It is soluble in alcohol and demonstrates limited solubility in water. The flash point (tag closed cup) is 100 °C (212 °F), which must be considered during handling and storage to ensure formulation safety. These properties support its incorporation into diverse flavor matrices, especially lipid-rich or alcoholic media.
FAQ
What is 2-hexyl thiophene and what are its main characteristics?
2-Hexyl thiophene is an organic sulfur-containing heterocyclic compound characterized by a molecular formula C10H16S. It exhibits a distinctive sulfurous odor with floral, fruity, and meaty undertones. The compound is used primarily as a flavoring agent in various food products, contributing complex aroma notes. It appears naturally in cooked meats like beef and lamb as well as in cranberry and mushroom, which underlines its role in food flavor profiles.
In which types of foods is 2-hexyl thiophene typically found or used?
2-Hexyl thiophene occurs naturally in roasted or cooked meats such as turkey, guinea hen, lamb, and beef, contributing to the characteristic aroma of these foods. It is also present in cranberry fruits and mushrooms. Its use as a flavoring agent extends to chicken, seafood, cucumber, and green vegetable flavors. These applications benefit from its sulfurous and green notes, enhancing the sensory qualities of the final product.
How is 2-hexyl thiophene regulated and what safety considerations apply?
The compound is evaluated under regulatory frameworks such as FEMA (US) and IFRA (Global) for use as a flavor ingredient. Safety assessments include intake limits and usage levels in various food categories to ensure consumer safety. It is classified under specific usage recommendations, with established maximum levels in meats, dairy, and processed fruits. Although 2-hexyl thiophene is classified as harmful if swallowed and irritating to skin and eyes according to some European hazard statements, no comprehensive GHS classification under OSHA HCS has been found. Proper handling with personal protective equipment is advised in industrial settings.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| NCBI | Start search |
Literature & References
| 2-hexylthiophene | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 18794-77-9 |
| Pubchem (cid): | 87793 |
| Pubchem (sid): | 135044354 |
| 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 |
| HMDB (The Human Metabolome Database): | HMDB32329 |
| FooDB: | FDB009582 |
| Export Tariff Code: | 2934.99.4400 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | 2-hexyl thiophene |
| Trivial Name | 2-Hexylthiophene |
| Short Description | 2-hexylthiophene |
| Formula | C10 H16 S |
| CAS Number | 18794-77-9 |
| FEMA Number | 4137 |
| Flavis Number | 15.076 |
| ECHA Number | 242-579-4 |
| FDA UNII | 82479467Q1 |
| Nikkaji Number | J47.701J |
| MDL | MFCD00022535 |
| COE Number | 11616 |
| xLogP3-AA | 4.40 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1764 2-hexylthiophene |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 18794-77-9 ; 2-HEXYLTHIOPHENE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 168.30252075195 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 7.748 to 7.814 |
| Refractive Index | 1.492 to 1.498 @ 20 °C |
| Boiling Point | 229 to 230°C @ 760 mm Hg |
| Vapor Pressure | 0.155 mmHg @ 25 °C |
| Vapor Density | 5.7 |
| Flash Point TCC Value | 100 °C TCC |
| logP (o/w) | 4.791 est |
| Solubility | |
| alcohol | Yes |
| water, 4.831 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Sulfurous | |
| floral, fruity, gassy, green, meaty | |
| General comment | At 0.10 % in dipropylene glycol. floral fruity gassy green meaty |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Celery |
| Flavoring purposes | Chicken , Cranberry , Cucumber , Green , Seafood |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 22 - Harmful if swallowed. R 36/38 - Irritating to skin and eyes. S 02 - Keep out of the reach of children. S 20/21 - When using do not eat, drink or smoke. 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: | |||
| flavoring agents | |||
| Recommendation for 2-hexyl thiophene usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.46 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 78 (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: 22 | |||
| Click here to view publication 22 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.20000 | 0.20000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | 0.50000 | 0.50000 | |
| confectionery froastings: | - | - | |
| egg products: | 1.00000 | 1.00000 | |
| fats / oils: | 0.20000 | 0.20000 | |
| fish products: | 1.00000 | 1.00000 | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | 1.00000 | 1.00000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | 1.00000 | 1.00000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | 1.00000 | 1.00000 | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 250.00000 | 250.00000 | |
| snack foods: | 0.20000 | 0.20000 | |
| soft candy: | - | - | |
| soups: | 1.00000 | 1.00000 | |
| 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): | 0.20000 | 1.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.10000 | 0.50000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.20000 | 1.00000 | |
| Processed fruit (04.1): | 0.20000 | 1.00000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 0.20000 | 1.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 0.10000 | 0.50000 | |
| Bakery wares (07.0): | 0.20000 | 1.00000 | |
| Meat and meat products, including poultry and game (08.0): | 0.10000 | 0.20000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.10000 | 0.20000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.10000 | 0.50000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 0.20000 | 1.00000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 0.10000 | 0.50000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 0.20000 | 1.00000 | |
| Ready-to-eat savouries (15.0): | 0.40000 | 2.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.10000 | 0.50000 | |
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 |
| 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 |
| Scientific Opinion on Flavouring Group Evaluation 21, Revision 2 (FGE.21Rev2): Thiazoles, thiophene, thiazoline and thienyl derivatives from chemical group 29. Miscellaneous substances from chemical group 30. View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 21, Revision 3 (FGE.21Rev3): Thiazoles, thiophenes, thiazoline and thienyl derivatives from chemical groups 29 and 30 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 21, Revision 5 (FGE.21Rev5): Thiazoles, thiophenes, thiazoline and thienyl derivatives from chemical groups 29 and 30 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 :87793 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2-hexylthiophene |
| Chemidplus:0018794779 |