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allyl thiopropionate
Allyl thiopropionate is a sulfur-containing ester with a fresh onion-garlic scent used as a flavoring agent in food products.
General Material Description
Allyl thiopropionate is an organosulfur compound classified as a thioester, specifically the S-2-propenyl ester of propanethioic acid. It appears as a colorless to pale-yellow liquid with a molecular formula of C6H10OS and a molecular weight of approximately 130.21 g/mol. Its odor profile is characterized as alliaceous, reminiscent of fresh onion and garlic with green, gassy nuances, which makes it valuable in flavor applications. Known also by synonyms such as S-allyl thiopropanoate and proionic acid thioacrylic ester, this compound can be sourced via chemical synthesis routes designed to replicate natural sulfur-containing flavors. Allyl thiopropionate is documented in chemical databases like PubChem and is used primarily in the flavor industry for its distinctive savory notes.
Occurrence, Applicability & Potential Uses
Allyl thiopropionate naturally resembles volatile sulfur compounds found in alliums such as garlic, onion, and leek, although industrially it is produced via synthesis. Its biological inspiration is rooted in these common vegetables, which impart characteristic alliaceous aromas. This compound’s distinctive fresh onion-garlic scent and flavor profile render it suitable for enhancing meat, vegetable, and seasoning flavors. It is employed extensively within the flavor industry as an additive to recreate or amplify savory notes. Regulatory guidelines such as the FEMA (US) GRAS status recognize allyl thiopropionate as a flavoring substance, reinforcing its acceptability in food applications within prescribed safe limits.
Physico-Chemical Properties Summary
Allyl thiopropionate is a liquid with physical properties favorable for flavor formulation, including a boiling point around 150 to 151 °C at standard atmospheric pressure, which indicates moderate volatility allowing its aroma to release during food preparation. Its specific gravity at 25 °C is approximately 0.898 to 0.902, while the refractive index ranges from 1.475 to 1.485 at 20 °C. The compound exhibits a modest vapor pressure of 3.667 mm Hg at 25 °C, indicating limited but sufficient volatility for sensory impact. Its estimated partition coefficient (log P) of about 2.09 suggests moderate lipophilicity, supporting solubility in alcohol and slight solubility in water. The flash point near 48 °C (119 °F) implies flammability under certain conditions, requiring attention during handling. These properties collectively influence its behavior in formulations, balancing stability with effective aroma delivery.
FAQ
What is allyl thiopropionate and how is it characterized?
Allyl thiopropionate is a sulfur-containing organic compound classified as a thioester. It is chemically known as the S-2-propenyl ester of propanethioic acid with molecular formula C6H10OS. The compound presents a distinctive alliaceous odor and flavor reminiscent of fresh onion and garlic, making it useful in flavoring applications. It typically appears as a clear to slightly yellow liquid and is used primarily as a food flavor additive.
Where is allyl thiopropionate commonly used and how is it applied?
Allyl thiopropionate is commonly used as a flavoring agent in food products to impart savory, garlic-like, and onion-like notes. It finds applications in enhancing flavors of meat, vegetable preparations, seasonings, and processed foods where alliaceous character is desirable. The compound’s use is regulated under FEMA (US) guidelines, and it is formulated at controlled concentrations to achieve the intended sensory effect without overwhelming the product.
What regulatory standards and safety measures apply to allyl thiopropionate?
Allyl thiopropionate is recognized by the FEMA (Flavor and Extract Manufacturers Association, US) as a generally recognized as safe (GRAS) flavoring substance, supporting its authorized use in food. Safety information indicates it is flammable and an irritant to eyes, skin, and respiratory system, thereby necessitating precautions in handling. While no specific OSHA Hazard Communication standards classify it as hazardous, standard industrial hygiene practices and compliance with national and international flavor additive regulations ensure safe use. Its purity and usage levels are delineated to maintain consumer safety.
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 |
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): | HMDB37493 |
| FooDB: | FDB016568 |
| Export Tariff Code: | 2915.50.3000 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| FAO: | Allyl thiopropionate |
General Material Information
| Preferred name | allyl thiopropionate |
| Trivial Name | S-Allyl thiopropionate |
| Short Description | propanethioic acid, S-2-propenyl ester |
| Formula | C6 H10 O S |
| CAS Number | 41820-22-8 |
| FEMA Number | 3329 |
| Flavis Number | 12.101 |
| FDA UNII | 95HUD1BW6G |
| Nikkaji Number | J1.539.211H |
| MDL | MFCD00209497 |
| COE Number | 11436 |
| xLogP3-AA | 1.80 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 490 allyl thiopropionate |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 41820-22-8 ; ALLYL THIOPROPIONATE |
| Synonyms |
|
Suppliers
| BOC Sciences | DeLong Chemicals America |
| Penta International | R C Treatt & Co Ltd |
| Santa Cruz Biotechnology | Synerzine |
| Penta International Corporation | Taytonn ASCC |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 130.20989990234 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 7.472 to 7.506 |
| Refractive Index | 1.475 to 1.485 @ 20 °C |
| Boiling Point | 150 to 151°C @ 760 mm Hg |
| Acid Value | 1 max KOH/g |
| Vapor Pressure | 3.667 mmHg @ 25 °C |
| Flash Point TCC Value | 48.33 °C TCC |
| logP (o/w) | 2.089 est |
| Solubility | |
| alcohol | Yes |
| water, 4266 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Alliaceous | |
| fresh, onion, garlic, green, gassy | |
| General comment | At 0.10 % in propylene glycol. fresh onion garlic green gassy |
| Mosciano, Gerard P&F 17, No. 1, 41, (1992) | Fresh onion garlic-like with green gassy nuances |
| Flavor Type: Alliaceous | |
| fresh, onion, green, sweet, vegetable | |
| Mosciano, Gerard P&F 17, No. 1, 41, (1992) | At 5.00 ppm. Fresh onion with a green sweet vegetable nuance |
Safety Information
Safety information
| European information : | |
| Most important hazard(s): | |
| Xi - Irritant | |
| R 10 - Flammable. R 36/37/38 - Irritating to eyes, respiratory system, and skin. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. 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: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| IFRA Purity Specification: | |||
| Recommendation for allyl thiopropionate usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | ND (μg/capita/day) | ||
| Structure Class: | I | ||
| 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: | - | 0.25000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | 0.25000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 0.25000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 0.25000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| soups: | - | 0.25000 | |
| 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 ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :61995 |
| National Institute of Allergy and Infectious Diseases:Data |
| WISER:UN 1993 |
| WGK Germany:3 |
| S-prop-2-enyl propanethioate |
| Chemidplus:0041820228 |