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dipropyl sulfide

Dipropyl sulfide is a sulfur-containing compound with an alliaceous odor used primarily as a flavoring agent in savory foods like garlic and roasted chicken.
Chemical Structure

General Material Description

Dipropyl sulfide, also known as 1,1'-thiobispropane, is an organosulfur compound with the molecular formula C6H14S. It appears as a clear liquid exhibiting a distinctive alliaceous odor reminiscent of garlic and onion. This compound has diverse synonyms including di-n-propyl thioether and propyl thiopropane, indicating its chemical structure as a sulfur atom bonded between two propyl groups. Dipropyl sulfide is available from chemical suppliers and can be identified through its PubChem entry (CID 8118). It is primarily isolated or synthesized for use as a flavoring agent due to its characteristic aromatic properties resembling those of roasted meat and allium vegetables. Its moderate hydrophobicity facilitates its incorporation into complex flavor systems.

Occurrence, Applicability & Potential Uses

Dipropyl sulfide occurs naturally in foods such as roasted chicken, garlic bulbs, mustard seeds, and onions, where it contributes to characteristic savory and alliaceous aromas. Its biological presence is associated with metabolic transformations of sulfur-containing amino acids and degradation products in allium vegetables. In applications, dipropyl sulfide is utilized chiefly as a flavoring agent to impart notes related to garlic, leek, meat, onion, savory, and vegetable profiles. Regulatory evaluation by FEMA (US) supports its controlled use in flavor formulations. Its incorporation can enhance the sensory complexity of culinary products, particularly those aiming to replicate or amplify roasted or sulfuraceous notes.

Physico-Chemical Properties Summary

Dipropyl sulfide has a molecular weight of approximately 118.24 g/mol and a molecular formula of C6H14S. It presents as a volatile liquid with a boiling point range of 142 to 143 °C at 760 mm Hg and a vapor pressure of about 6.4 mm Hg at 25 °C. The compound exhibits moderate hydrophobicity, with an estimated logP of 3.015, indicating lipophilicity favorable for partitioning into organic phases. Its specific gravity ranges between 0.835 and 0.845 at 20 °C, and it refracts light with an index from 1.446 to 1.454 under the same temperature conditions. Dipropyl sulfide is soluble in alcohol and sparingly soluble in water. Its flash point is approximately 89 °F (around 32 °C), reflecting moderate flammability. These properties influence its handling, formulation, and volatility in flavor systems.

FAQ

What is dipropyl sulfide and what are its main characteristics?
Dipropyl sulfide is an organosulfur compound characterized by a sulfur atom bonded to two propyl groups, giving the formula C6H14S. It is a clear volatile liquid with an alliaceous odor reminiscent of garlic and onion. Commonly known as 1,1'-thiobispropane or di-n-propyl thioether, it is used chiefly as a flavoring agent in food products to provide savory and roasted meat notes.
Where does dipropyl sulfide occur naturally and how is it used in flavoring?
Dipropyl sulfide naturally occurs in foods such as roasted chicken, garlic bulbs, mustard, and onions, contributing to their characteristic aromas. In flavoring applications, it is used to enhance notes related to garlic, leek, meat, onion, and other savory vegetable profiles. Its incorporation aids in replicating or intensifying complex sulfurous and savory sensory attributes in culinary products.
What safety considerations and regulations apply to dipropyl sulfide in flavoring uses?
Dipropyl sulfide is classified as flammable and an irritant to eyes, skin, and the respiratory system under European regulations. It is recommended for use only as a flavoring agent and not for fragrance applications. Regulatory assessments such as those by FEMA (US) provide guidelines on its usage levels. Handling precautions include avoiding skin or eye contact and minimizing inhalation exposure. Comprehensive safety data sheets are available for detailed hazard information.

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

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Literature & References

1-propylsulfanylpropane
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:111-47-7
Pubchem (cid):8118
Pubchem (sid):134975029
Publications by PubMed
Primary Ion Depletion Kinetics (PIDK) Studies as a New Tool for Investigating Chemical Ionization Fragmentation Reactions with PTR-MS.
Using metal complex ion-molecule reactions in a miniature rectilinear ion trap mass spectrometer to detect chemical warfare agents.
S-alk(en)ylmercaptocysteine: chemical synthesis, biological activities, and redox-related mechanism.
Structure and function relationship study of allium organosulfur compounds on upregulating the pi class of glutathione S-transferase expression.
Band gap effect on the photocatalytic activity of supramolecular structures obtained by entrapping photosensitizers in different inorganic supports.
Experimental and theoretical studies of the reaction of the OH radical with alkyl sulfides: 3. Kinetics and mechanism of the OH initiated oxidation of dimethyl, dipropyl, and dibutyl sulfides: reactivity trends in the alkyl sulfides and development of a predictive expression for the reaction of OH with DMS.
Organosulfur compounds alone or in combination with vitamin C protect towards N-nitrosopiperidine- and N-nitrosodibutylamine-induced oxidative DNA damage in HepG2 cells.
Efficacy of a novel biofilter in hatchery sanitation: II. Removal of odorogenous pollutants.
Protective effects of organosulfur compounds towards N-nitrosamine-induced DNA damage in the single-cell gel electrophoresis (SCGE)/HepG2 assay.
Aquasonolysis of thioethers.
Modulation of cytochrome P450 enzymes by organosulfur compounds from garlic.
Effects of food materials on removal of Allium-specific volatile sulfur compounds.
Relative activities of organosulfur compounds derived from onions and garlic in increasing tissue activities of quinone reductase and glutathione transferase in rat tissues.
Antimutagenic activity of organosulfur compounds from Allium is associated with phase II enzyme induction.
Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies.
Liver subcellular fractions from rats treated by organosulfur compounds from Allium modulate mutagen activation.
Inhibition of cholesterol biosynthesis by organosulfur compounds derived from garlic.
Modulation of phase II enzymes by organosulfur compounds from allium vegetables in rat tissues.
Effects of oil-soluble organosulfur compounds from garlic on doxorubicin-induced lipid peroxidation.
Differential induction of NAD(P)H:quinone oxidoreductase by anti-carcinogenic organosulfides from garlic.
Modification of hepatic drug-metabolizing enzymes in rats treated with alkyl sulfides.
Induction of glutathione S-transferase pi as a bioassay for the evaluation of potency of inhibitors of benzo(a)pyrene-induced cancer in a murine model.
Mechanism of differential efficacy of garlic organosulfides in preventing benzo(a)pyrene-induced cancer in mice.
Glutathione S-transferases of female A/J mouse lung and their induction by anticarcinogenic organosulfides from garlic.
Glutathione S-transferases of female A/J mouse liver and forestomach and their differential induction by anti-carcinogenic organosulfides from garlic.
Enhancement by organosulfur compounds from garlic and onions of diethylnitrosamine-induced glutathione S-transferase positive foci in the rat liver.
Fate of dipropyl sulphide and dipropyl sulphoxide in rat.
Aerobic and anaerobic degradation of a range of alkyl sulfides by a denitrifying marine bacterium.
Effect of alkyl sulfides on diazomethane-induced methylation of DNA in vitro.
Effects of organosulfur compounds from garlic and onions on benzo[a]pyrene-induced neoplasia and glutathione S-transferase activity in the mouse.

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):HMDB31431
FooDB:FDB003594
Export Tariff Code:2930.90.9999
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

General Material Information

Preferred name dipropyl sulfide
Trivial Name Propyl sulfide
Short Description 1,1'-thiobispropane
Formula C6 H14 S
CAS Number 111-47-7
Flavis Number 12.015
ECHA Number 203-873-8
FDA UNII Q6J7GNX8F9
Nikkaji Number J373E
Beilstein Number 1719002
MDL MFCD00009379
COE Number 541
xLogP3-AA 2.70 (est)
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • di-n-propyl sulfide
  • di-n-propylsulfide
  • dipropyl sulphide
  • dipropyl thioether
  • propane, 1,1'-thiobis-
  • propyl monosulfide
  • 1-propyl sulfanyl propane
  • 1-( propylsulfanyl)propane
  • 1-propylsulfanylpropane
  • propylthiopropane
  • 1,1'- sulfanediyldipropane
  • sulfide, dipropyl
  • 4-thiaheptane
  • 1,1'- thiobispropane
  • 1,1'- thiodipropane
  • 1-propylsulfanylpropane
  • Propane, 1,1′-thiobis-
  • Propyl sulfide
  • 1,1′-Thiobis[propane]
  • 4-Thiaheptane
  • n-Propyl sulfide
  • Di-n-propyl thioether
  • NSC 78429
  • 1-Propylsulfanyl-propane
  • 1-(Propylsulfanyl)propane

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 118.24257659912
Specific gravity @ 20 °C
Pounds per Gallon 6.956 to 7.039
Refractive Index 1.446 to 1.454 @ 20 °C
Boiling Point 142 to 143°C @ 760 mm Hg
Vapor Pressure 6.419 mmHg @ 25 °C
Vapor Density 4
Flash Point TCC Value 31.67 °C TCC
logP (o/w) 3.015 est
Solubility
alcohol Yes
water, 351.1 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

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

Occurrences

Potential Uses

Applications
Flavoring purposes Garlic , Leek , Meat , Onion , Savory , Vegetable

Safety Information

Safety information

Preferred SDS: View
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 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 dipropyl sulfide usage levels up to:
not for fragrance use.

Safety references

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):111-47-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :8118
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1993
WGK Germany:3
1-propylsulfanylpropane
Chemidplus:0000111477