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2-ethyl benzene thiol
2-ethyl benzene thiol is a sulfurous, phenolic flavor compound with CAS number 4500-58-7 used primarily as a flavoring agent in food products.
General Material Description
2-ethyl benzene thiol, also known as 2-ethylthiophenol, is an organosulfur compound characterized by a benzene ring substituted with both an ethyl group at the ortho position and a thiol (-SH) functional group. It has the molecular formula C8H10S and a molecular weight of approximately 138.23 g/mol. This compound appears as a liquid exhibiting a distinct sulfurous and phenolic odor profile. Its sensory notes include roasted, smoky, and meaty nuances, making it valuable in flavoring applications. Synonyms such as o-ethylbenzenethiol and 2-ethyl phenyl mercaptan are commonly encountered. The compound is linked to its PubChem entry (CID 3734338) for detailed chemical information. It is typically sourced through synthetic organic chemistry routes involving aromatic substitution and thiolation reactions.
Occurrence, Applicability & Potential Uses
2-ethyl benzene thiol occurs primarily as a synthetic flavoring agent rather than naturally in biological systems. Its distinctive sulfurous and phenolic aroma notes render it suitable for enhancing nut flavors and contributing smoky, meaty aspects to food products. Regulatory evaluation and use levels are guided by FEMA (US), with FEMA number 3345 assigned to this compound. The flavoring agent is applied in various food categories including baked goods, soups, and frozen dairy, though use concentrations are carefully monitored. It is not commonly used in fragrance formulations. The compound's odor attributes also suggest potential explorations in mimicking natural food aromas and in flavor adjuncts requiring sulfurous sensory qualities.
Physico-Chemical Properties Summary
2-ethyl benzene thiol exhibits several physico-chemical properties influencing its handling and formulation. It has a boiling range between 203 and 205°C at standard atmospheric pressure and a relatively low vapor pressure of 0.275 mmHg at 25°C, indicating moderate volatility. The flash point is approximately 83°C (177°F), reflecting its flammability characteristics. The compound has a calculated octanol-water partition coefficient (log P) of about 3.5, suggesting considerable hydrophobicity. Its specific gravity at 20°C lies between 1.035 and 1.039, and the refractive index ranges from 1.568 to 1.572 at the same temperature. Solubility data indicate it is somewhat soluble in alcohol and water at 25°C (estimated 56.24 mg/L) but is generally not freely miscible in water. The material remains stable in various media, supporting its utility in diverse flavoring preparations.
FAQ
What is 2-ethyl benzene thiol and what are its main characteristics?
2-ethyl benzene thiol is an organosulfur compound with a benzene ring substituted by an ethyl group and a thiol (-SH) group at the ortho position. It typically appears as a liquid with a molecular formula of C8H10S and a molecular weight of 138.23 g/mol. The compound exhibits distinct sulfurous, phenolic, smoky, and meaty odor and flavor notes. It is known by various synonyms such as 2-ethylthiophenol and o-ethylbenzenethiol. This compound is primarily used in flavoring applications, valued for its ability to impart complex savory and nutty sensory qualities.
Where is 2-ethyl benzene thiol used and how is it applied in flavors?
2-ethyl benzene thiol is utilized mainly as a flavoring agent in food products where sulfurous and smoky notes enhance the overall aroma profile. Its applications include usage in baked goods, soups, frozen dairy products, and items requiring nut-like or meaty flavor components. The compound's FEMA (US) listing number is 3345, providing regulatory guidance for its use levels. It is not commonly used in fragrances but finds its niche within flavor formulations to enrich savory and roasted profiles. The ingredient is carefully dosed due to its potent odor characteristics.
What regulations govern 2-ethyl benzene thiol and how is its safety managed?
2-ethyl benzene thiol is regulated under FEMA (US) standards for flavoring substances, where its usage and exposure levels are assessed for safety within food applications. The compound has a FEMA number 3345 and has been evaluated for Generally Recognized As Safe (GRAS) status at specified concentrations. Safety data indicate it may cause irritation to eyes, skin, and respiratory system; proper handling includes avoiding direct contact and exposure. Exposure limits are established based on scientific assessments, and current use recommendations restrict its application to flavoring rather than fragrance products. Comprehensive toxicological studies support its controlled use under guideline levels.
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-ethylbenzenethiol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 4500-58-7 |
| Pubchem (cid): | 3734338 |
| Pubchem (sid): | 135263854 |
| Publications by US Patents | |
| 3,952,024 - Furfurylthioacetone | |
| Certain 2,5-dimethyl-3-thiopyrazines | |
| Flavoring agent | |
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): | HMDB41361 |
| FooDB: | FDB021284 |
| Export Tariff Code: | 2930.90.2900 |
| ChemSpider: | View |
| FAO: | 2-Ethyl(thiophenol) |
General Material Information
| Preferred name | 2-ethyl benzene thiol |
| Trivial Name | 2-Ethylbenzenethiol |
| Short Description | 2-(ethylthio)phenol |
| Formula | C8 H10 S |
| CAS Number | 4500-58-7 |
| FEMA Number | 3345 |
| Flavis Number | 12.054 |
| ECHA Number | 224-811-6 |
| FDA UNII | 62GBU45I5P |
| Nikkaji Number | J205.879K |
| MDL | MFCD00010022 |
| COE Number | 11666 |
| NMR Predictor | External link |
| JECFA Food Flavoring | 529 2-ethylthiophenol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 4500-58-7 ; 2-ETHYLTHIOPHENOL |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 138.2326965332 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | 8.622 to 8.656 |
| Refractive Index | 1.568 to 1.572 @ 20 °C |
| Boiling Point | 203 to 205°C @ 760 mm Hg |
| Vapor Pressure | 0.275 mmHg @ 25 °C |
| Flash Point TCC Value | 80.56 °C TCC |
| logP (o/w) | 3.511 est |
| Solubility | |
| alcohol | Yes |
| water, 56.24 mg/L @ 25 °C (est) | Yes |
| water | No |
| Stability | |
| stable in most media | Unspecified |
Organoleptic Properties
| Odor Type: Sulfurous | |
| sulfurous, roasted, meaty, smoky | |
| General comment | At 0.10 % in propylene glycol. sulfurous roasted meaty smoky |
| Flavor Type: Phenolic | |
| phenolic, smoky, meaty | |
| General comment | Phenolic smoky meaty |
Potential Uses
| Applications | |
| Flavoring purposes | Nut |
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 - Wear suitable protective clothing. | |
| 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-ethyl benzene thiol usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.00012 (μg/capita/day) | ||
| Structure Class: | III | ||
| 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: 6 | |||
| Click here to view publication 6 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 0.30000 | |
| beverages(nonalcoholic): | - | 0.20000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 0.20000 | |
| fruit ices: | - | 0.20000 | |
| gelatins / puddings: | - | 0.20000 | |
| granulated sugar: | - | - | |
| gravies: | - | 0.20000 | |
| hard candy: | - | 0.30000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 0.20000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | 0.20000 | |
| 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 8 (FGE.08)[1]: Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical group 20 View page or View pdf |
| Flavouring Group Evaluation 8, Revision 1 (FGE.08Rev1): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 8, Revision 3 (FGE.08Rev3): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 08, Revision 4 (FGE.08Rev4): Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical groups 20 and 30 View page or View pdf |
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):4500-58-7 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :3734338 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| 2-ethylbenzenethiol |
| Chemidplus:0004500587 |