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vinyl sulfurol
Vinyl sulfurol is 4-methyl-5-vinylthiazole, a flavor and fragrance agent with nutty and cocoa-like notes used in bakery, cocoa, coffee, and meat products.
General Material Description
Vinyl sulfurol, chemically known as 4-methyl-5-vinylthiazole, is an organic sulfur-containing heterocyclic compound belonging to the thiazole class. This compound has the molecular formula C6H7NS and a molecular weight of approximately 125.19 g/mol. It appears as a moderately volatile liquid with an aromatic profile characterized by nutty, musty, and cocoa-like odor notes. Synonyms for this compound include 5-ethenyl-4-methyl thiazole and 4-methyl-5-vinyl-1,3-thiazole. Vinyl sulfurol is recognized by authoritative chemical databases such as PubChem and is sourced primarily through chemical synthesis. It is widely used in flavor and fragrance development due to its potent sensory characteristics and is naturally present in several foods and beverages.
Occurrence, Applicability & Potential Uses
Vinyl sulfurol naturally occurs in various biological sources including cocoa, coffee, brandy grape brandy, cognac, roasted hazelnuts (filbert), garlic bulbs, and passion fruit. Its scent and flavor profile comprise nutty, musty, earthy, and root vegetable-like notes with cocoa powder likeness, making it a valuable additive in flavor formulation. The compound finds applications across bakery items, confectionery, meat products, soups, and beverages, adding characteristic hazelnut, nutty, and potato-like nuances. The use of vinyl sulfurol aligns with regulatory standards such as FEMA (US), which assigns it the number 3313, and JECFA, which evaluates its safety and usage levels within the food industry. The compound’s versatility in both odor and flavor purposes enhances sensory qualities in multiple culinary contexts.
Physico-Chemical Properties Summary
Vinyl sulfurol exhibits a complex balance of physical and chemical properties that influence its application in formulations. It has a boiling point range from approximately 173 to 174°C at atmospheric pressure and lower boiling points under reduced pressure, indicating moderate volatility suitable for controlled release in flavors and fragrances. The substance possesses a specific gravity between 1.088 and 1.102 at 25°C and a refractive index ranging from 1.555 to 1.575 at 20°C, reflecting its liquid state at ambient conditions. The estimated logP value of 1.55 suggests moderate lipophilicity, supporting solubility in both aqueous and alcoholic media, as confirmed by its solubility in alcohol and water. With a vapor density higher than air, it disperses effectively in gaseous phases. Its flash point of 159°F (approx. 71°C) requires appropriate handling precautions. Collectively, these properties support its use as a stable yet perceptible flavor and fragrance compound under normal manufacturing and usage environments.
FAQ
What is vinyl sulfurol and what are its sensory characteristics?
Vinyl sulfurol, also known as 4-methyl-5-vinylthiazole, is a sulfur-containing heterocyclic compound used primarily as a flavor and fragrance agent. It is characterized by nutty, musty, and earthy odor and flavor notes with cocoa and root vegetable nuances. These sensory attributes make it valuable in food and fragrance formulations where nutty or cocoa-like tones are desired.
Where does vinyl sulfurol naturally occur and how is it used?
This compound naturally appears in foods such as cocoa, coffee, roasted hazelnuts, garlic bulbs, and alcoholic beverages like brandy and cognac. Commercially, vinyl sulfurol is utilized to impart nutty and cocoa-like flavors in bakery products, meat, soups, confectionery, and beverages. Its dual role in flavor and fragrance formulations enhances complex sensory profiles in these applications.
What regulations and safety guidelines apply to vinyl sulfurol for use in food and fragrance products?
Vinyl sulfurol is regulated under standards including FEMA (US) with FEMA number 3313 and JECFA (FAO/WHO), which have evaluated its safety as a flavoring substance. The International Fragrance Association’s Code of Practice sets usage limits, recommending up to 0.05% concentration in fragrance concentrates. Safety data indicate it is harmful if inhaled or ingested in large amounts, necessitating appropriate handling and adherence to maximum usage levels to ensure consumer safety.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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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): | HMDB31858 |
| FooDB: | FDB008542 |
| Export Tariff Code: | 2934.10.0090 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | vinyl sulfurol |
| Trivial Name | 4-Methyl-5-vinylthiazole |
| Short Description | 4-methyl-5-vinylthiazole |
| Formula | C6 H7 N S |
| CAS Number | 1759-28-0 |
| FEMA Number | 3313 |
| Flavis Number | 15.018 |
| ECHA Number | 217-160-4 |
| FDA UNII | 1G77935P78 |
| Nikkaji Number | J24.662J |
| Beilstein Number | 0107867 |
| MDL | MFCD00005337 |
| COE Number | 11633 |
| xLogP3-AA | 2.20 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 1038 4-methyl-5-vinylthiazole |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 1759-28-0 ; 4-METHYL-5-VINYLTHIAZOLE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 125.19378662109 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.053 to 9.17 |
| Refractive Index | 1.555 to 1.575 @ 20 °C |
| Boiling Point | 78 to 80°C @ 25 mm Hg |
| Boiling Point | 173 to 174°C @ 760 mm Hg |
| Vapor Pressure | 0.962 mmHg @ 25 °C |
| Vapor Density | 4.3 |
| Flash Point TCC Value | 70.56 °C TCC |
| logP (o/w) | 1.552 est |
| Solubility | |
| alcohol | Yes |
| water | Yes |
| water, 787.9 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Nutty | |
| musty, nutty, rooty, vegetable, cocoa, root beer | |
| General comment | At 0.10 % in dipropylene glycol. musty nutty root vegetable cocoa |
| Mosciano, Gerard P&F 16, No. 2, 49, (1991) | Diffusive, musty, nutty, root vegetable-like |
| Flavor Type: Nutty | |
| nutty, musty, earthy, cocoa, powdery | |
| Mosciano, Gerard P&F 16, No. 2, 49, (1991) | At 20.00 ppm. Nutty, musty, earthy, cocoa powder like |
| Used in bakery and desserts at 10ppm, and in meat products and soups at 5ppm, also in frozen and sweet confectionery. | Nutty |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Passion fruit |
| Flavoring purposes | Bakery , Chocolate cocoa , Coffee , Filbert , Hazelnut , Meat , Nut , Potato , Soup |
| Other purposes | Confection |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 01/02 - Keep locked up and 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. S 45 - In case of accident or if you feel unwell seek medical advice immediately. | |
| 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: | |
| oral-mouse LD50 400 mg/kg Drug and Chemical Toxicology. Vol. 3, Pg. 249, 1980. | |
| 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 vinyl sulfurol usage levels up to: | |||
| 0.0500 % in the fragrance concentrate. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 2.10 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.20 (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: 5 | |||
| Click here to view publication 5 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 8.00000 | |
| beverages(nonalcoholic): | - | 2.00000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 2.00000 | |
| fruit ices: | - | 2.00000 | |
| gelatins / puddings: | - | 8.00000 | |
| granulated sugar: | - | - | |
| gravies: | - | 6.00000 | |
| hard candy: | - | 2.00000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 6.00000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | 6.00000 | |
| 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 |
| 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 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 |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):1759-28-0 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :15654 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 5-ethenyl-4-methyl-1,3-thiazole |
| Chemidplus:0001759280 |
| RTECS:XJ5104000 for cas# 1759-28-0 |