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3,5-diisopropyl-1,2,4-trithiolane

3,5-diisopropyl-1,2,4-trithiolane is a sulfur-based compound notable for its strong meaty, bacon-like odor used as a flavoring agent in food products.

General Material Description

3,5-diisopropyl-1,2,4-trithiolane is a heterocyclic organosulfur compound with the molecular formula C8H16S3. It forms part of the 1,2,4-trithiolane family, characterized by a five-membered ring containing three sulfur atoms. This compound exhibits a strong, meaty odor reminiscent of crispy bacon when diluted at low concentrations in propylene glycol. Also known by synonyms such as 3,5-di(propan-2-yl)-1,2,4-trithiolane and 1,2,4-trithiolane, 3,5-bis(1-methylethyl)-, it is primarily utilized as a flavoring agent to impart savory and meat-related sensory characteristics. The compound is referenced in controlled-vocabulary databases including PubChem. It is typically synthesized for industrial use rather than extracted directly from natural sources.

Occurrence, Applicability & Potential Uses

3,5-diisopropyl-1,2,4-trithiolane is found predominantly in flavor formulations aimed at reproducing meat and bacon profiles. Its biological occurrence is not prominent; rather, it is an industrially produced compound used to enhance flavor complexity in food products. It can contribute to the aroma profiles of hawthorn and other savory goods. Regulatory assessments including those by FEMA (Flavor and Extract Manufacturers Association, US) support its approval as a flavoring agent. Due to its distinctive odor and functional properties, it is used selectively in flavor systems targeting meat and bacon sensory characteristics.

Physico-Chemical Properties Summary

This compound has a molecular weight of approximately 208.41 g/mol and an estimated log P value around 4.3 to 5.5, indicating relatively high lipophilicity, which influences its solubility and distribution in flavor matrices. It has a boiling range of 279 to 281°C under standard atmospheric pressure (760 mmHg) and a low vapor pressure of 0.006 mmHg at 25°C, reflecting low volatility under ambient conditions. The flash point is about 248°F (approximately 120°C), limiting its flammability risk under normal handling environments. 3,5-diisopropyl-1,2,4-trithiolane displays solubility in alcohol and very low estimated water solubility near 14.93 mg/L at 25°C. These properties affect formulation choices in application development, impacting its delivery in aqueous versus lipid-based systems.

FAQ

What is 3,5-diisopropyl-1,2,4-trithiolane and what are its main characteristics?
3,5-diisopropyl-1,2,4-trithiolane is a sulfur-containing heterocyclic compound with a distinctive meaty and crispy bacon-like odor. Its chemical structure includes a trithiolane ring with isopropyl substituents, giving it unique sensory properties for flavor applications. It is recognized mainly as a flavor ingredient used to impart savory notes.
How is 3,5-diisopropyl-1,2,4-trithiolane used and where does it typically occur?
This compound is principally employed as a flavoring agent to enhance meat and bacon flavor profiles in food products. While it does not occur naturally in significant amounts, it is synthetically prepared for industrial flavor use. Its applications include incorporation in savory formulations to boost aroma complexity reminiscent of cooked meat and bacon.
What safety and regulatory considerations apply to 3,5-diisopropyl-1,2,4-trithiolane for flavor use?
3,5-diisopropyl-1,2,4-trithiolane is classified as safe for use as a flavoring agent under guidelines such as those from FEMA (US). No specific hazard classifications or precautionary statements have been identified according to OSHA standards. Usage limits and intake estimations are established by regulatory bodies to ensure its safe incorporation in food products without posing health risks, based on available toxicological data.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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General Material Information

Preferred name 3,5-diisopropyl-1,2,4-trithiolane
Trivial Name 3,5-di(propan-2-yl)-1,2,4-trithiolane
Short Description 3,5-di-isopropyl-1,2,4-trithiolane
Formula C8 H16 S3
CAS Number 54934-99-5
Flavis Number 15.048
FDA UNII Search
Nikkaji Number J101.783G
xLogP3-AA 4.30 (est)
NMR Predictor External link
Synonyms
  • 3,5-di-isopropyl-1,2,4-trithiolane
  • 3,5-di(propan-2-yl)-1,2,4-trithiolane
  • 1,2,4-trithiolane, 3,5-bis(1-methylethyl)-

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 208.41052246094
Boiling Point 279 to 281°C @ 760 mm Hg
Vapor Pressure 0.006 mmHg @ 25 °C
Flash Point TCC Value 120 °C TCC
logP (o/w) 5.487 est
Solubility
alcohol Yes
water, 14.93 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Meaty
meaty, bacon, smoky
General comment At 0.01 % in propylene glycol. powerful crispy bacon

Potential Uses

Applications
Odor purposes Hawthorn
Flavoring purposes Bacon , Meat

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 3,5-diisopropyl-1,2,4-trithiolane usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.0061 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 46 (μg/person/day)
Threshold of Concern:540 (μg/person/day)
Structure Class: II
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): 0.020001.00000
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): --
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 8 (FGE.08)[1]: Aliphatic and alicyclic mono-, di-, tri-, and polysulphides with or without additional oxygenated functional groups from chemical group 20
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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)
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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
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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)
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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

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EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :529049
National Institute of Allergy and Infectious Diseases:Data
3,5-di(propan-2-yl)-1,2,4-trithiolane