We have found
46590
results matching your criteria.
Please wait while we search...
benzyl disulfide
Benzyl disulfide is an organosulfur compound used as a flavoring agent imparting smoky and caramel notes, naturally present in roasted cocoa and onions.
General Material Description
Benzyl disulfide (C14H14S2) is an organosulfur compound with the molecular formula C14H14S2. It appears as a pale yellow to colorless solid and is also known by various synonyms including dibenzyl disulfide, benzyldisulfanylmethylbenzene, and alpha-(benzyl dithio) toluene. This compound exhibits a characteristic smoky odor with burnt, earthy green, and caramel nuances evident at low concentrations such as 0.10% in propylene glycol. Benzyl disulfide is naturally found in roasted cocoa and onions, contributing significantly to their aroma profiles. It is utilized primarily as a flavoring agent to impart caramel and smoke notes in various food applications. For chemical reference, it is indexed under the controlled vocabulary identifier ChEBI:72752. Its extraction or synthesis routes generally involve organosulfur chemistry pathways.
Occurrence, Applicability & Potential Uses
This compound occurs naturally in foods such as roasted cocoa and onions. Benzyl disulfide is valued in the flavor industry for its ability to provide smoky and caramel flavor notes, making it suitable for enhancing the sensory qualities of various food products. It finds application in flavoring agents, especially where smoky characteristics are desired. Regulatory frameworks including the FEMA (US) standard recognize benzyl disulfide as FEMA number 3617, permitting its use as a flavoring substance under specific levels. It is recommended for use within maximum concentration limits in diverse food categories to ensure consumer safety and flavor integrity.
Physico-Chemical Properties Summary
Benzyl disulfide is a sulfur-containing compound with a molecular weight of approximately 246.4 g/mol. It melts between 71 and 73°C at standard atmospheric pressure. The compound exhibits a relatively high log P value estimated at 4.95, indicating significant lipophilicity, which affects its solubility and behavior in formulations. It is sparingly soluble in water with an estimated solubility of 0.75 mg/L at 25°C, while showing better solubility in hot ether and ethyl alcohol. Its vapor pressure is very low at 2.0 × 10-5 mmHg at 25°C, and it has a high flash point of 423°F, suggesting low volatility and flammability under normal conditions. These properties influence its stability and performance in flavor formulations, where controlled release and solubility are critical.
FAQ
What is benzyl disulfide and what are its key characteristics?
Benzyl disulfide is an organosulfur compound recognized for its distinctive smoky and caramel-like aroma. Chemically, it consists of two benzyl groups linked by a disulfide bond and has the molecular formula C14H14S2. It naturally appears in roasted cocoa and onions, contributing to their complex aroma profiles. The compound is a pale yellow to colorless solid with moderate melting point and low volatility, and it is primarily used as a flavoring agent in food products.
Where does benzyl disulfide occur naturally and how is it used in flavor applications?
Benzyl disulfide naturally occurs in roasted cocoa and onions, where it contributes smoky and caramel sensory notes. In flavor applications, it is used to replicate or enhance smoky and caramel flavors in food products such as baked goods, confectionery frosts, and other processed foods. Its chemical stability and low volatility make it well-suited for these purposes, allowing controlled flavor release and longevity in the final products.
What regulations apply to benzyl disulfide and how is it sourced for use?
Benzyl disulfide is regulated by organizations such as the Flavor and Extract Manufacturers Association (FEMA) in the United States, under the FEMA number 3617, which designates it as a generally recognized as safe (GRAS) flavoring substance when used within prescribed levels. It is typically sourced through chemical synthesis or extraction methods aligned with industry standards and safety protocols. Regulatory assessments including those by FEMA and bodies such as EFSA (European Food Safety Authority) evaluate its safety and appropriate usage concentrations in food products.
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
| benzyldisulfanylmethylbenzene | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 150-60-7 |
| Pubchem (cid): | 9012 |
| Pubchem (sid): | 134973080 |
| 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 |
| CHEBI: | View |
| CHEMBL: | View |
| UM BBD: | Search |
| HMDB (The Human Metabolome Database): | HMDB32077 |
| FooDB: | FDB008792 |
| Export Tariff Code: | 2930.90.2900 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | Benzyl disulfide |
General Material Information
| Preferred name | benzyl disulfide |
| Trivial Name | Dibenzyl disulfide |
| Short Description | dibenzyl disulfide |
| Formula | C14 H14 S2 |
| CAS Number | 150-60-7 |
| Deleted CAS Number | 325737-14-2 |
| FEMA Number | 3617 |
| Flavis Number | 12.081 |
| ECHA Number | 205-764-0 |
| FDA UNII | BG7680605N |
| Nikkaji Number | J60.275B |
| Beilstein Number | 1110443 |
| MDL | MFCD00004783 |
| xLogP3-AA | 3.90 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 579 benzyl disulfide |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 150-60-7 ; BENZYL DISULFIDE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 246.39558410645 |
| Melting Point | 71 to 73°C @ 760 mm Hg |
| Vapor Pressure | 2.0E-5 mmHg @ 25 °C |
| Flash Point TCC Value | 217.2 °C TCC |
| logP (o/w) | 4.951 est |
| Solubility | |
| ether, hot | Yes |
| ethyl alcohol, hot | Yes |
| ethyl alcohol, very slightly | Yes |
| water, 0.7537 mg/L @ 25 °C (est) | Yes |
Organoleptic Properties
| Odor Type: Smoky | |
| smoky, burnt, earthy, green, caramellic | |
| General comment | At 0.10 % in propylene glycol. smoky burnt earthy green caramel |
Occurrences
| (data available) |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 22 - Harmful if swallowed. R 36/37 - Irritating to eyes and respiratory system. R 43 - May cause sensitisation by skin contact. S 02 - Keep out of the reach of children. S 22 - Do not breath dust. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 36/37 - Wear suitable protective clothing and gloves. | |
| 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 benzyl disulfide usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.012 (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: 12 | |||
| Click here to view publication 12 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 1.00000 | |
| beverages(nonalcoholic): | - | 1.30000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 1.30000 | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | 1.30000 | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 1.00000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | 1.30000 | |
| soups: | - | - | |
| 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 74 (FGE.74)[1]: Consideration of Simple Aliphatic Sulphides and Thiols evaluated by JECFA (61st meeting) Structurally related to Aliphatic and Alicyclic Mono-, Di-, Tri-, and Polysulphides with or without Additional Oxygenated Functional Groups from Chemical Group 20 evaluated by EFSA in FGE.08 (2008) 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 |
| Flavouring Group Evaluation 91 (FGE.91): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by JECFA (53rd and 68th meetings) structurally related to aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups evaluated by EFSA in FGE.08Rev1 (2009) 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 |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):150-60-7 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :9012 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:2 |
| benzyldisulfanylmethylbenzene |
| Chemidplus:0000150607 |
| RTECS:JO1750000 for cas# 150-60-7 |