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allyl sulfide
Allyl sulfide is a sulfur-containing compound known for its sulfurous, garlic-like odor, widely used as a flavoring and perfuming agent.
General Material Description
Allyl sulfide is an organosulfur compound with the molecular formula C6H10S. It presents as a liquid with a distinct sulfurous odor reminiscent of garlic, horseradish, and onion, reflecting its sulfur-containing nature. Known also by synonyms such as diallyl sulfide and 2-propenyl sulfide, allyl sulfide is a key component in various natural extracts, particularly garlic oil. Its structure consists of two allyl groups connected by a sulfur atom, contributing to its characteristic aroma and flavor. This compound is widely recognized in flavor chemistry and fragrance industries for imparting sulfurous, pungent notes. More details and chemical data are available through controlled vocabularies such as ChEBI. Allyl sulfide is primarily sourced from garlic and related Allium species, and it can also be found in mustard, horseradish, and other sulfur-rich plants.
Occurrence, Applicability & Potential Uses
Allyl sulfide naturally occurs in various Allium vegetables including garlic bulbs, garlic oil, onion oil, leek, and wild leek, as well as in mustard, horseradish root, radish root, and garden cress oil. It contributes significantly to the characteristic sulfurous aroma and flavor profile of these plants. In the food industry, allyl sulfide functions as a flavoring agent to mimic or enhance garlic, onion, and related savory notes in products such as condiments, sauces, and snack foods. Cosmetic applications include its use as a perfuming agent to impart sulfurous or spicy nuances in fragrance formulations. Regulatory frameworks such as FEMA (US) provide guidelines for allyl sulfide’s use in flavorings to ensure safety and standardized application levels. Its presence also influences sensory characteristics in roasted beef and other cooked meat products, linking allyl sulfide to complex flavor development during food processing.
Physico-Chemical Properties Summary
Allyl sulfide is a liquid at ambient temperature with a molecular weight of approximately 114.21 g/mol. It exhibits a boiling point range between 138 and 139 °C at standard atmospheric pressure, indicating moderate volatility. The compound possesses a specific gravity close to 0.89 at 25 °C and a refractive index around 1.49 at 20 °C, characteristics relevant for quality control and formulation. Its vapor pressure measures about 9.22 mmHg at 25 °C, highlighting its potential for volatilization in flavor and fragrance applications. Allyl sulfide displays solubility in solvents such as alcohol and ether, while water solubility is limited but estimated at roughly 620.5 mg/L at 25 °C. The compound's log P value around 2.6 indicates moderate hydrophobicity, influencing its behavior in emulsions and product matrices. Its flash point is approximately 45 °C (113 °F), classifying it as a flammable substance and necessitating appropriate handling precautions.
FAQ
What is allyl sulfide and where does it naturally occur?
Allyl sulfide is an organosulfur compound characterized by its sulfurous and garlic-like odor. It naturally occurs in the Allium family of plants, notably garlic bulbs and garlic oil, as well as in onion and leek. It is also present in mustard, horseradish root, radish root, and other plants rich in sulfur compounds. This occurrence contributes to the signature flavors and aromas of these foods.
How is allyl sulfide used in flavoring and cosmetic applications?
Allyl sulfide serves as a flavoring agent that imparts sulfurous sensory notes associated with garlic, onion, horseradish, and related savory flavors. It is utilized in food products to enhance or replicate these distinctive tastes. In cosmetics, allyl sulfide is employed as a perfuming agent to introduce sulfurous or spicy nuances in fragrances. Its formulation requires careful control due to its volatility, odor strength, and flammability.
What safety regulations and standards apply to allyl sulfide in food and fragrance use?
Allyl sulfide is regulated under standards such as FEMA (US) for flavoring agents and IFRA (Global) for fragrance ingredients. Usage levels in food are monitored to maintain safety, with established maximum limits in various food categories. Occupational safety guidelines highlight its flammability and potential irritation to eyes and respiratory tract, necessitating appropriate handling measures. Detailed safety assessments from agencies like EFSA and JECFA provide evaluations on its toxicity and recommended exposure thresholds.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| PubMeb | Start search |
| NCBI | Start search |
Literature & References
| 3-prop-2-enylsulfanylprop-1-ene | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 592-88-1 |
| Pubchem (cid): | 11617 |
| Pubchem (sid): | 134977839 |
| Publications by PubMed | |
| Diallyl sulfide, a flavor component of garlic (Allium sativum), inhibits dimethylhydrazine-induced colon cancer. | |
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 |
| KEGG (GenomeNet): | C08370 |
| HMDB (The Human Metabolome Database): | HMDB36491 |
| FooDB: | FDB015388 |
| Export Tariff Code: | 2930.90.2900 |
| MedlinePlusSupp: | View |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | Allyl sulfide |
General Material Information
| Preferred name | allyl sulfide |
| Trivial Name | Diallyl sulfide |
| Short Description | 2-propenyl sulfide |
| Formula | C6 H10 S |
| CAS Number | 592-88-1 |
| Deleted CAS Number | 132879-26-6 |
| FEMA Number | 2042 |
| Flavis Number | 12.088 |
| ECHA Number | 209-775-1 |
| FDA UNII | 60G7CF7CWZ |
| Nikkaji Number | J6.765B |
| Beilstein Number | 1736016 |
| MDL | MFCD00008658 |
| COE Number | 11846 |
| xLogP3-AA | 2.20 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 458 allyl sulfide |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 592-88-1 ; ALLYL SULFIDE |
| Synonyms |
|
Suppliers
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 114.21070098877 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.381 to 7.422 |
| Refractive Index | 1.488 to 1.492 @ 20 °C |
| Boiling Point | 138 to 139°C @ 760 mm Hg |
| Vapor Pressure | 9.22 mmHg @ 25 °C |
| Vapor Density | 3.9 |
| Flash Point TCC Value | 45 °C TCC |
| logP (o/w) | 2.61 |
| Solubility | |
| alcohol | Yes |
| ether | Yes |
| water, 620.5 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Sulfurous | |
| sulfurous, onion, garlic, horseradish, metallic, pungent | |
| General comment | At 0.10 % in propylene glycol. sulfurous onion garlic horseradish metallic |
| Mosciano, Gerard P&F 22, No. 3, 47, (1997) | Pungent, sulfurous, onion-garlic and horseradish-like with a metallic nuance |
| Flavor Type: Sulfurous | |
| sulfurous, onion, garlic, vegetable, radish | |
| Mosciano, Gerard P&F 22, No. 3, 47, (1997) | At 2.00 ppm. Sulfurous, onion-garlic and vegetative radish-like with a slightly hot nuance |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Odor purposes | Asafoetida |
| Flavoring purposes | Asafoetida , Chive , Durian , Garlic , Horseradish , Jackfruit , Leek , Onion , Radish , Savory , Scallion , Shallot , Wasabi |
| Cosmetic purposes | Perfuming agents |
Safety Information
Safety information
| Preferred SDS: View | |
| European information : | |
| Most important hazard(s): | |
| Xn - Harmful. | |
| R 10 - Flammable. R 20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R 36/37 - Irritating to eyes and respiratory system. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. S 23 - Do not breath vapour. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 3/7/9 - Keep container tightly closed in a cool well-ventilated place. 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 2980 mg/kg Food and Chemical Toxicology. Vol. 26, Pg. 299, 1988. intravenous-rabbit LD50 330 mg/kg Biochemical Journal. Vol. 4, Pg. 107, 1909. | |
| Dermal Toxicity: | |
| skin-rabbit LD50 > 5000 mg/kg Food and Chemical Toxicology. Vol. 26, Pg. 299, 1988. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents and cosmetic fragrance agents | |||
| IFRA Purity Specification: | |||
| Recommendation for allyl sulfide usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 15.44 (μg/capita/day) | ||
| Maximised Survey-derived Daily Intakes (MSDI-USA): | 0.40 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 1413 (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: 3 | |||
| Click here to view publication 3 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 0.05000 | |
| beverages(nonalcoholic): | - | 0.04000 | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | 13.00000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | 0.06000 | |
| fruit ices: | - | 0.06000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | - | 0.07000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 3.70000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | - | |
| 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): | 0.01000 | 1.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.01000 | 0.50000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.01000 | 1.00000 | |
| Processed fruit (04.1): | - | - | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | 0.01000 | 1.00000 | |
| Confectionery (05.0): | 0.04000 | 1.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 0.01000 | 0.50000 | |
| Bakery wares (07.0): | 7.67000 | 10.00000 | |
| Meat and meat products, including poultry and game (08.0): | 9.22000 | 10.00000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.01000 | 0.20000 | |
| Eggs and egg products (10.0): | 0.01000 | 0.20000 | |
| Sweeteners, including honey (11.0): | 0.01000 | 0.20000 | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 8.90000 | 10.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | - | - | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 0.01000 | 0.50000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 0.01000 | 0.10000 | |
| Ready-to-eat savouries (15.0): | - | - | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.01000 | 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 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 74, Revision 2 (FGE.74Rev2): Consideration of Simple Aliphatic Sulphides and Thiols evaluated by the JECFA (53rd and 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.08Rev3 (2011) 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 |
| Scientific Opinion on the safety and efficacy of aliphatic and aromatic mono- and di-thiols and mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups (chemical group 20) when used as flavourings for all animal species View page or View pdf |
| EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF) View page or View pdf |
| Scientific Opinion on Flavouring Group Evaluation 74, Revision 4 (FGE.74Rev4): Consideration of aliphatic sulphides and thiols evaluated by JECFA (53rd and 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.08Rev5 View page or View pdf |
| EPI System: View |
| ClinicalTrials.gov:search |
| Chemical Carcinogenesis Research Information System:Search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):592-88-1 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :11617 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 1993 |
| WGK Germany:2 |
| 3-prop-2-enylsulfanylprop-1-ene |
| Chemidplus:0000592881 |
| RTECS:BC4900000 for cas# 592-88-1 |