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S-prenyl thioisobutyrate
S-prenyl thioisobutyrate is a sulfur-containing flavoring compound with a tropical fruity odor, utilized mainly as a food flavor additive.
General Material Description
S-prenyl thioisobutyrate, also known by its systematic name S-(3-methyl-2-buten-1-yl) 2-methylpropanethioate, is a sulfur-containing organic compound classified as a thioester. It appears as a clear substance with typical physicochemical properties associated with sulfurous volatile compounds. This compound is notable for its characteristic odor, described as sulfurous with tropical fruity notes reminiscent of durian and passion fruit, which arises from its inclusion of the prenyl group and thioester functional group. Synonyms include prenyl thioisobutyrate and several variations reflecting its chemical structure. It is referenced in scientific databases such as PubChem for detailed chemical and safety information. S-prenyl thioisobutyrate is typically obtained via synthesis for use as a flavoring agent, originally identified in natural sources like buchu, a plant known for sulfurous aromatic compounds.
Occurrence, Applicability & Potential Uses
This compound naturally occurs in the buchu plant, where it contributes to the distinctive sulfurous aroma characteristic of this botanical. Its sensory profile makes it valuable as a flavoring agent in the food industry, particularly to impart complex sulfurous fruity notes. S-prenyl thioisobutyrate finds potential uses across various food product categories, including baked goods, beverages, confectionery, and savory seasonings. Its inclusion is regulated under frameworks such as FEMA (US), where it holds the FEMA number 4760. The compound’s properties align with usage in trace amounts to enhance flavor profiles without overpowering other ingredients.
Physico-Chemical Properties Summary
The physicochemical profile of S-prenyl thioisobutyrate reveals specific characteristics influencing its formulation in flavors. It has a molecular weight of approximately 172.29 g/mol and a moderately lipophilic nature inferred from an estimated logP value around 3.5, indicating preferential solubility in non-polar solvents such as alcohols over water. Its vapor pressure is low, about 0.2 mmHg at 25 °C, which affects its volatility and sensory longevity in applications. The compound’s specific gravity ranges between 1.109 and 1.115 at 25 °C, while its refractive index lies from 1.483 to 1.489 at 20 °C. A flash point estimated near 71 °C (160 °F) highlights considerations for handling and storage. Solubility tests denote good solubility in alcohol and limited solubility in water, consistent with its structural features. These properties collectively determine its behavior in flavor formulations and compatibility with diverse food matrices.
FAQ
What is S-prenyl thioisobutyrate and what are its primary characteristics?
S-prenyl thioisobutyrate is a sulfur-containing thioester compound used predominantly as a flavoring agent in foods. It is recognized for its distinct sulfurous odor with fruity tropical notes reminiscent of durian and passion fruit. Its molecular formula is C9H16OS, and it appears as a clear substance with moderate volatility. The compound is also known by several chemical synonyms reflecting its structure.
Where does S-prenyl thioisobutyrate naturally occur and how is it used in flavoring applications?
This compound is naturally found in the buchu plant, contributing to the plant’s sulfurous aromatic profile. In flavor applications, S-prenyl thioisobutyrate is added to foods to impart complex sulfurous and tropical fruit notes. It is incorporated in products such as baked goods, alcoholic and non-alcoholic beverages, confectionery, and condiments. Its use is controlled to maintain balance within flavor profiles and ensure safety.
What regulations govern the use and safety of S-prenyl thioisobutyrate in food products?
Use of S-prenyl thioisobutyrate as a flavoring agent is regulated by FEMA (US), where it is assigned the FEMA number 4760. It is evaluated within flavor safety assessments, including considerations by the FEMA Expert Panel confirming it as generally recognized as safe (GRAS) under specified usage limits. Regulatory documents detail recommended maximum usage levels for various food categories to ensure consumer safety. Toxicity data are limited, and no specific classification under OSHA HCS (29 CFR 1910) indicates significant hazards.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| 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 |
| HMDB (The Human Metabolome Database): | HMDB31699 |
| FooDB: | FDB008362 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
General Material Information
| Preferred name | S-prenyl thioisobutyrate |
| Trivial Name | S-(3-Methyl-2-buten-1-yl) 2-methylpropanethioate |
| Short Description | S-(3-methyl-2-buten-1-yl) 2-methylpropanethioate |
| Formula | C9 H16 O S |
| CAS Number | 53626-94-1 |
| FEMA Number | 4760 |
| Flavis Number | 12.196 |
| FDA UNII | 7HQZ604M8H |
| Nikkaji Number | J390.559D |
| xLogP3-AA | 3.20 (est) |
| NMR Predictor | External link |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| Synonyms |
|
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 172.29072570801 |
| Specific gravity | @ 25 °C |
| Pounds per Gallon | 9.228 to 9.278 |
| Refractive Index | 1.483 to 1.489 @ 20 °C |
| Vapor Pressure | 0.2 mmHg @ 25 °C |
| Flash Point TCC Value | 71.3 °C TCC |
| logP (o/w) | 3.51 est |
| Solubility | |
| alcohol | Yes |
| water, 185.8 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Sulfurous | |
| sulfurous, fruity, tropical, durian, passion fruit | |
| General comment | At 0.10 % in propylene glycol. sulfurous fruity tropical durian passion fruit |
Occurrences
| (data available) |
Safety Information
Safety information
| 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 S-prenyl thioisobutyrate usage levels up to: | |||
| not for fragrance use. | |||
| Maximised Survey-derived Daily Intakes (MSDI-EU): | 0.012 (μg/capita/day) | ||
| Modified Theoretical Added Maximum Daily Intake (mTAMDI): | 160 (μg/person/day) | ||
| Threshold of Concern: | 1800 (μg/person/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: 26 | |||
| Click here to view publication 26 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 0.01000 | 0.50000 | |
| beverages(nonalcoholic): | 0.01000 | 0.50000 | |
| beverages(alcoholic): | 0.01000 | 0.50000 | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 0.03000 | 1.00000 | |
| condiments / relishes: | 0.01000 | 0.50000 | |
| confectionery froastings: | 0.01000 | 0.50000 | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | 0.01000 | 0.50000 | |
| hard candy: | 0.01000 | 0.50000 | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | 0.01000 | 0.50000 | |
| meat products: | - | - | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | 0.00100 | 0.50000 | |
| processed vegetables: | 0.00100 | 0.50000 | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | 0.01000 | 0.05000 | |
| snack foods: | 0.01000 | 0.05000 | |
| soft candy: | 0.01000 | 0.05000 | |
| soups: | 0.01000 | 0.05000 | |
| 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): | 0.40000 | 2.00000 | |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0): | 0.20000 | 1.00000 | |
| Edible ices, including sherbet and sorbet (03.0): | 0.40000 | 2.00000 | |
| Processed fruit (04.1): | 0.30000 | 1.50000 | |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): | - | - | |
| Confectionery (05.0): | 0.40000 | 2.00000 | |
| Chewing gum (05.3): | - | - | |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): | 0.20000 | 1.00000 | |
| Bakery wares (07.0): | 0.40000 | 2.00000 | |
| Meat and meat products, including poultry and game (08.0): | 0.10000 | 0.40000 | |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): | 0.10000 | 0.40000 | |
| Eggs and egg products (10.0): | - | - | |
| Sweeteners, including honey (11.0): | - | - | |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0): | 0.20000 | 1.00000 | |
| Foodstuffs intended for particular nutritional uses (13.0): | 0.40000 | 2.00000 | |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1): | 0.20000 | 1.00000 | |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): | 0.40000 | 2.00000 | |
| Ready-to-eat savouries (15.0): | 1.00000 | 5.00000 | |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): | 0.20000 | 1.00000 | |
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 |
| Flavouring Group Evaluation 08 Rev2 (FGE.08 Rev2): 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 |
| Scientific Opinion on Flavouring Group Evaluation 08, Revision 5 (FGE.08Rev5): 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 :71438214 |
| National Institute of Allergy and Infectious Diseases:Data |
| S-(3-methyl-2-buten-1-yl) 2-methylpropanethioate |
| Chemidplus:0053626941 |