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2,6-dimethyl thiophenol
2,6-dimethyl thiophenol is a sulfurous aromatic compound featuring a meaty, roasted scent used primarily as a flavoring agent in meat and broth products.
General Material Description
2,6-dimethyl thiophenol is an aromatic organosulfur compound characterized by a benzene ring substituted with methyl groups at the 2 and 6 positions and a thiol (-SH) group. It has the molecular formula C8H10S and a molecular weight of approximately 138.23 g/mol. The compound appears as a liquid with persistent sulfurous and meaty odor notes. It is known under several synonyms including 2,6-dimethylbenzenethiol and 2,6-xylyl mercaptan. Classified chemically as a thiophenol derivative, it is listed in authoritative chemical resources such as PubChem. This compound is typically sourced synthetically, although it occurs naturally in boiled beef extracts where it contributes to characteristic flavor notes.
Occurrence, Applicability & Potential Uses
2,6-dimethyl thiophenol naturally occurs as a component in boiled beef, contributing to its distinctive aroma. It is applied primarily as a flavoring agent to impart sulfurous, meaty, roasted, and phenolic sensory characteristics to food products. Its use is documented under FEMA (US) with the number 3666 and has been evaluated for safety and usage levels in various food categories including baked goods, beverages, and meat products. The compound’s properties allow it to enhance the flavor profile of broth, beef, and meat preparations, making it valuable in food flavor formulation where a roasted or meat-like aroma is desired.
Physico-Chemical Properties Summary
The compound exhibits moderate volatility with a boiling point ranging from 218 to 219 °C at standard atmospheric pressure and a flash point measured at 186 °F (approximately 85 °C). It has a specific gravity of about 1.044 at 20 °C, indicating it is slightly denser than water. The refractive index ranges from 1.521 to 1.527 at 20 °C, reflecting its optical density. Its estimated logP value of 3.15 denotes lipophilicity, consistent with its good solubility in fats and slight solubility in water (approximately 50 mg/L at 25 °C). Vapor pressure at 25 °C is low (0.187 mmHg), suggesting limited volatility under ambient conditions. These physicochemical properties influence its behavior in flavor formulations, affecting stability, volatility, and miscibility with lipid or aqueous matrices.
FAQ
What is 2,6-dimethyl thiophenol and what are its sensory characteristics?
2,6-dimethyl thiophenol is an aromatic sulfur-containing compound characterized by a benzene ring with two methyl groups and a thiol moiety. It imparts a distinct sulfurous, meaty, roasted, and phenolic aroma with a slightly smoky and metallic nuance. Used predominantly as a flavoring agent, it contributes savory and roasted notes, making it useful in enhancing meat-related flavors.
Where is 2,6-dimethyl thiophenol found and how is it used in flavor applications?
This compound occurs naturally in boiled beef, where it plays a role in the characteristic cooked meat aroma. Its use as a flavoring agent extends to various food products such as beef, broth, and other meat preparations. The compound is incorporated to provide sulfurous and roasted aromas that enhance the sensory profile of these foods.
How is 2,6-dimethyl thiophenol regulated and what safety considerations apply?
2,6-dimethyl thiophenol is regulated as a flavoring substance under FEMA (US) with the FEMA number 3666. Usage levels are established to ensure safety in various food categories. It is assessed for safety by organizations including EFSA (EU) and the FEMA Expert Panel. Its oral toxicity in rats shows an LD50 of approximately 3150 mg/kg. Safety measures recommend avoiding skin and eye contact, with precautions in handling due to its irritant properties. Use is restricted to flavoring purposes and the compound is not intended for fragrance applications.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| 2,6-dimethylbenzenethiol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 118-72-9 |
| Pubchem (cid): | 61045 |
| Pubchem (sid): | 135018855 |
| Publications by PubMed | |
| Mechanistic studies and methods to prevent aglycon transfer of thioglycosides. | |
| Monomeric, one- and two-dimensional networks incorporating (2,6-Me2C6H3S)2Pb building blocks. | |
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): | HMDB32019 |
| FooDB: | FDB008717 |
| Export Tariff Code: | 2930.90.9999 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | 2,6-Dimethyl(thiophenol) |
General Material Information
| Preferred name | 2,6-dimethyl thiophenol |
| Trivial Name | 2,6-Dimethylbenzenethiol |
| Short Description | 2,6-dimethyl(thiophenol) |
| Formula | C8 H10 S |
| CAS Number | 118-72-9 |
| FEMA Number | 3666 |
| Flavis Number | 12.082 |
| ECHA Number | 204-272-3 |
| FDA UNII | 3A223G78P4 |
| Nikkaji Number | J155.603G |
| MDL | MFCD00010021 |
| xLogP3-AA | 2.80 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 530 2,6-dimethyl(thiophenol) |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 118-72-9 ; 2,6-DIMETHYLTHIOPHENOL |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 138.2326965332 |
| Specific gravity | @ 20 °C |
| Pounds per Gallon | |
| Refractive Index | 1.527 to 1.521 @ 20 °C |
| Boiling Point | 218 to 219°C @ 760 mm Hg |
| Vapor Pressure | 0.187 mmHg @ 25 °C |
| Flash Point TCC Value | 85.56 °C TCC |
| logP (o/w) | 3.15 |
| Solubility | |
| fats | Yes |
| water, slightly | Yes |
| water, 50.36 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Sulfurous | |
| sulfurous, meaty, roasted, phenolic, metallic, smoky | |
| General comment | At 0.10 % in propylene glycol. sulfury meaty roasted phenolic metallic |
| Mosciano, Gerard P&F 21, No. 6, 49, (1996) | Meaty, roasted, phenolic, sulfurous and smokey |
| Flavor Type: Meaty | |
| meaty, vegetable, nutty, sulfurous | |
| Mosciano, Gerard P&F 21, No. 6, 49, (1996) | Meaty, vegetative and nutty with a slight sulfurous nuance |
Occurrences
| (data available) |
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: | |
| oral-rat LD50 [sex: M,F (5/sex/group)] 3150 mg/kg (Mondino & Peano, 1979a) | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for 2,6-dimethyl thiophenol usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 1.30 (μg/capita/day) | ||
| NOEL (No Observed Effect Level): | 0.43 (mg/kg bw per 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: 13 | |||
| Click here to view publication 13 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 3.00000 | |
| beverages(nonalcoholic): | - | 0.05000 | |
| beverages(alcoholic): | - | 0.05000 | |
| breakfast cereal: | - | 3.00000 | |
| cheese: | - | 0.50000 | |
| chewing gum: | - | 5.00000 | |
| condiments / relishes: | - | 0.50000 | |
| confectionery froastings: | - | 0.50000 | |
| egg products: | - | 0.50000 | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | 0.25000 | |
| granulated sugar: | - | - | |
| gravies: | - | 0.50000 | |
| hard candy: | - | 2.50000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 1.00000 | |
| milk products: | - | 0.50000 | |
| nut products: | - | 0.50000 | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | 5.00000 | |
| soft candy: | - | 1.50000 | |
| soups: | - | 2.00000 | |
| 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 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):118-72-9 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :61045 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| 2,6-dimethylbenzenethiol |
| Chemidplus:0000118729 |