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propenyl propyl disulfide
Propenyl propyl disulfide is a sulfur-containing compound used mainly as a flavoring agent contributing cooked onion and sulfurous notes.
General Material Description
Propenyl propyl disulfide is an organosulfur compound characterized by its molecular formula C6H12S2 and moderate molecular weight around 148.29 g/mol. This volatile substance features a distinctive sulfurous odor reminiscent of cooked onion, contributing to its role in food flavorings. Common synonyms include 1-propenyl propyl disulfide and prop-1-enyl propyl disulfide. It is listed under the chemical identifier InChIKey AAPBYIVJOWCMGH-UHFFFAOYSA-N and appears within flavoring contexts such as those documented by FEMA (US). The compound is typically derived from natural sources like onion (Allium cepa), chive, and is also present in blood orange oil from Italy. For further chemical reference, see its PubChem entry.
Occurrence, Applicability & Potential Uses
Propenyl propyl disulfide occurs naturally in several botanical sources including onion, chive, and blood orange oil, where it is found at notable concentrations such as approximately 5.90% in Italian blood orange oil. In flavor formulation, it imparts sulfurous and cooked onion notes that are valuable in replicating or enhancing savory and tropical fruit flavor profiles. Its recognized use as a flavoring agent is supported by FEMA (US) under number 3227 and it is assessed by IFRA (Global) and REACH (EU) frameworks for safety in food applications. Common applications include flavoring in products related to chive, onion, and certain fruit-flavored goods where a sulfurous note is desired.
Physico-Chemical Properties Summary
Propenyl propyl disulfide displays physical properties influencing its behavior in flavor applications. It has a moderate molecular weight and a logP value estimated around 3.18, suggesting lipophilicity suitable for flavor matrices involving oils and alcohols. It shows partial solubility in alcohol and minimal solubility in water, with an estimated water solubility near 53 mg/L at 25 °C. Its refractive index ranges from 1.522 to 1.532 at 20 °C. The compound has a relatively low boiling point between 78 and 80 °C under reduced pressure, which indicates volatility compatible with flavor release during heating. The flash point measured at 148 °F (approximately 64 °C) also informs handling and formulation conditions. Vapor pressure around 0.936 mmHg at 25 °C underlines its moderately volatile nature. These combined physicochemical traits make it a useful sulfurous flavor component in various food systems.
FAQ
What is propenyl propyl disulfide and what are its key characteristics?
Propenyl propyl disulfide is an organosulfur compound featuring the molecular formula C6H12S2. It exhibits a sulfurous odor reminiscent of cooked onion, making it significant in flavor applications. Known also as 1-propenyl propyl disulfide, it naturally occurs in Allium species such as onions and chives, as well as in blood orange oil. It has moderate volatility and partial solubility in alcohols, which supports its use in food flavorings where sulfurous notes are required.
In which foods or natural sources is propenyl propyl disulfide found, and how is it used?
This compound is found in natural sources like onion, chive, and blood orange oil, with a concentration around 5.90% in some blood orange oils from Italy. It is utilized mainly as a flavoring agent to impart sulfurous cooked onion-like notes in savory and tropical fruit flavor profiles. Its application covers products where enhancing natural onion or chive aromas is desirable. Due to its physicochemical properties, it blends well in oil and alcoholic matrices commonly used in flavor formulation.
What regulations govern the use of propenyl propyl disulfide in flavorings, and how is it sourced?
Propenyl propyl disulfide is regulated under FEMA (US) with number 3227 and is assessed within international frameworks such as IFRA (Global) and REACH (EU) to ensure safe use in flavor applications. It is predominantly sourced from natural extracts of Allium species and citrus oils. The FEMA Expert Panel considers its use as generally recognized as safe (GRAS) when applied within approved limits, especially in baked goods, condiments, and soups up to specified ppm levels. Users should consult relevant regulatory documents for detailed usage guidelines.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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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): | HMDB41392 |
| FooDB: | FDB021327 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| FAO: | Propenyl propyl disulfide |
General Material Information
| Preferred name | propenyl propyl disulfide |
| Trivial Name | 1-Propenyl propyl disulfide |
| Short Description | prop-1-enyl propyl disulfide |
| Formula | C6 H12 S2 |
| CAS Number | 5905-46-4 |
| FEMA Number | 3227 |
| Flavis Number | 12.044 |
| ECHA Number | 227-604-9 |
| FDA UNII | 0368A7K9E5 |
| Nikkaji Number | J223.874H |
| COE Number | 11699 |
| xLogP3-AA | 2.50 (est) |
| NMR Predictor | External link |
| JECFA Food Flavoring | 570 propenyl propyl disulfide |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm | 5905-46-4 ; PROPENYL PROPYL DISULFIDE |
| Synonyms |
|
Suppliers
| BOC Sciences | Jiangyin Healthway |
| Penta International | R C Treatt & Co Ltd |
| Jiangyin Healthway International Trade Co., Ltd | Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 148.29164123535 |
| Refractive Index | 1.522 to 1.532 @ 20 °C |
| Boiling Point | 78 to 80°C @ 13 mm Hg |
| Vapor Pressure | 0.936 mmHg @ 25 °C |
| Flash Point TCC Value | 64.44 °C TCC |
| logP (o/w) | 3.182 est |
| Solubility | |
| alcohol | Yes |
| water, 53.29 mg/L @ 25 °C (est) | Yes |
| water | No |
Organoleptic Properties
| Odor Type: Sulfurous | |
| sulfurous, onion cooked onion | |
| General comment | At 0.10 % in propylene glycol. sulfurous cooked onion |
Occurrences
| (data available) |
Potential Uses
| Applications | |
| Flavoring purposes | Chive , Fruit tropical fruit , Onion |
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 propenyl propyl disulfide 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: 4 | |||
| Click here to view publication 4 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | - | 2.00000 | |
| beverages(nonalcoholic): | - | - | |
| beverages(alcoholic): | - | - | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | - | - | |
| condiments / relishes: | - | 2.00000 | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | - | - | |
| fruit ices: | - | - | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | 2.00000 | |
| hard candy: | - | - | |
| imitation dairy: | - | - | |
| instant coffee / tea: | - | - | |
| jams / jellies: | - | - | |
| meat products: | - | 2.00000 | |
| milk products: | - | - | |
| nut products: | - | - | |
| other grains: | - | - | |
| poultry: | - | - | |
| processed fruits: | - | - | |
| processed vegetables: | - | - | |
| reconstituted vegetables: | - | - | |
| seasonings / flavors: | - | - | |
| snack foods: | - | - | |
| soft candy: | - | - | |
| 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 ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5320722 |
| National Institute of Allergy and Infectious Diseases:Data |
| 1-propyldisulfanylprop-1-ene |
| Chemidplus:0005905464 |