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ethyl propyl trisulfide

Ethyl propyl trisulfide is a sulfurous compound used as a flavoring agent contributing garlic and onion notes, found naturally in durian fruit.

General Material Description

Ethyl propyl trisulfide, also known as 1-(ethyltrisulfanyl)propane and 3,4,5-trithiaoctane, is an organosulfur compound characterized by a molecular formula of C5H12S3 and a molecular weight of approximately 168.35 g/mol. This compound displays a distinctive sulfurous sensory profile often described as alliaceous, resembling garlic and green onion odors when diluted in propylene glycol. Its chemical structure includes three sulfur atoms linked in a chain, making it part of the trisulfide chemical family. Ethyl propyl trisulfide is naturally found in the durian fruit and serves as a flavoring agent in food applications. More detailed chemical information is accessible via PubChem. The compound is typically obtained through extraction or synthetic processes geared toward flavor formulation.

Occurrence, Applicability & Potential Uses

This trisulfide compound occurs naturally in the durian fruit, contributing to its characteristic aroma. In flavor applications, ethyl propyl trisulfide is utilized to impart savory, garlic, and onion notes to various food products. Its deployment spans categories such as baked goods, beverages, dairy, and snack foods in controlled concentrations. Regulatory bodies including FEMA (US) have recognized it as a flavoring agent under the FEMA GRAS program. Its applications are confined to flavoring purposes rather than fragrance use due to its strong sulfurous odor. The compound aligns with specific regulatory guidelines and thresholds to ensure appropriate and safe use in food formulation.

Physico-Chemical Properties Summary

Ethyl propyl trisulfide possesses a molecular weight of 168.35 g/mol and features a moderately high boiling range of 234 to 237 °C at atmospheric pressure, indicating relative thermal stability. Its specific gravity ranges between 1.07 and 1.087 at standard ambient temperatures (20–25 °C), suggesting a density slightly greater than water. The compound exhibits a low vapor pressure of 0.0642 mmHg at 25 °C, reflecting moderate volatility. It is soluble in alcohol and sparingly soluble in water, with an estimated aqueous solubility of 86.84 mg/L at 25 °C. Its estimated log P value is about 4.52, indicating lipophilic character favorable for blending with hydrophobic matrices. The flash point is approximately 203 °F (~95 °C), which informs handling and storage safety considerations. These properties influence its formulation behavior and volatility in savory flavor applications.

FAQ

What is ethyl propyl trisulfide and where is it found naturally?
Ethyl propyl trisulfide is an organosulfur compound known for its sulfurous and alliaceous odor reminiscent of garlic and onion. It naturally occurs in durian fruit, contributing to the fruit's distinctive smell. Chemically, it is classified as a trisulfide, containing three linked sulfur atoms, and is used primarily as a food flavoring agent due to its savory sensory properties.
How is ethyl propyl trisulfide used in flavoring, and what are its sensory characteristics?
This compound is used in flavor formulations to deliver garlic, onion, and savory notes, particularly in baked goods, beverages, dairy products, and snack foods. Its sensory profile at low concentrations includes a pronounced sulfurous aroma with green onion and alliaceous nuances. Ethyl propyl trisulfide's lipophilic nature and volatility allow it to blend effectively into various flavor systems where such aromatic qualities are desired.
What safety and regulatory considerations are associated with ethyl propyl trisulfide?
Ethyl propyl trisulfide is recognized by FEMA (US) as a generally recognized as safe (GRAS) flavoring substance, with usage limits defined for multiple food categories. Though classified as an irritant in European regulations, it lacks specific hazard statements under OSHA's GHS classification. Safety precautions include avoiding eye and skin contact and using protective equipment during handling. It is not intended for fragrance applications, and regulatory evaluations by EFSA (EU) and JECFA provide comprehensive safety assessments guiding its use in food flavorings.

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):Search
FooDB:FDB009408
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

General Material Information

Preferred name ethyl propyl trisulfide
Trivial Name 1-(ethyltrisulfanyl)propane
Short Description 3,4,5-trithiaoctane
Formula C5 H12 S3
CAS Number 31499-70-4
FEMA Number 4042
Flavis Number 12.256
FDA UNII 4SOS6O9G2X
xLogP3-AA 2.60 (est)
NMR Predictor External link
JECFA Food Flavoring 1695 ethyl propyl trisulfide
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 31499-70-4 ; ETHYL PROPYL TRISULFIDE
Synonyms
  • ethyl propyl trisulphide
  • 1-( ethyltrisulfanyl)propane
  • propyl ethyl trisulfide
  • trisulfide, ethyl propyl
  • 3,4,5-trithiaoctane

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 168.34564208984
Specific gravity @ 20 °C
Pounds per Gallon 8.914 to 9.055
Specific gravity @ 25 °C
Pounds per Gallon 8.903 to 9.045
Refractive Index 1.549 to 1.559 @ 20 °C
Boiling Point 234 to 237°C @ 760 mm Hg
Vapor Pressure 0.0642 mmHg @ 25 °C
Flash Point TCC Value 95 °C TCC
logP (o/w) 4.52 est
Solubility
alcohol Yes
water, 86.84 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Sulfurous
alliaceous, garlic, onion green onion, onion
General comment At 0.10 % in propylene glycol. alliaceous garlic green onion

Occurrences

Potential Uses

Applications
Flavoring purposes Garlic , Onion , Savory , Vegetable

Safety Information

Safety information

European information :
Most important hazard(s):
Xi - Irritant
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
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
Recommendation for ethyl propyl trisulfide usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.012 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): ND (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 78 (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: 21
Click here to view publication 21
average usual ppmaverage maximum ppm
baked goods: 0.050000.10000
beverages(nonalcoholic): 0.020000.05000
beverages(alcoholic): 0.020000.05000
breakfast cereal: --
cheese: --
chewing gum: 0.100000.20000
condiments / relishes: 0.030000.06000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 0.030000.06000
fruit ices: 0.020000.05000
gelatins / puddings: --
granulated sugar: --
gravies: 0.030000.06000
hard candy: 0.040000.08000
imitation dairy: 0.020000.04000
instant coffee / tea: --
jams / jellies: --
meat products: 0.030000.06000
milk products: 0.020000.05000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: 0.030000.06000
soft candy: 0.030000.06000
soups: 0.030000.06000
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/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 0.200001.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 0.100000.50000
Edible ices, including sherbet and sorbet (03.0): 0.200001.00000
Processed fruit (04.1): 0.200001.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 0.200001.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 0.100000.50000
Bakery wares (07.0): 0.200001.00000
Meat and meat products, including poultry and game (08.0): 0.100000.20000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 0.100000.20000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 0.100000.50000
Foodstuffs intended for particular nutritional uses (13.0): 0.200001.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 0.100000.50000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 0.200001.00000
Ready-to-eat savouries (15.0): 0.400002.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 0.100000.50000

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 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 91, Revision 1 (FGE.91Rev1): 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.08Rev3 (2011)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 91, Revision 2 (FGE.91Rev2): Consideration of simple aliphatic and aromatic sulphides and thiols evaluated by the 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.08Rev5 (2012)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 91, Revision 3 (FGE.91Rev3): consideration of aliphatic, aromatic and a,ß-unsaturated sulfides and thiols evaluated by JECFA (53rd, 61st, 68th and 76th meetings), structurally related to substances in FGE.08Rev5
View page or View pdf

EPI System: View
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EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :53425122
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1-(ethyltrisulfanyl)propane
Chemidplus:0031499704