6028-61-1

Basic information

• Product Name: Dipropyl trisulfide
• Synonyms: FEMA 3276;DIPROPYL TRISULFIDE;DIPROPYL TRISULPHIDE;1,3-Dipropyltrisulfane;Di-n-propyl trisulfide;Trisulfide, dipropyl;PROPYL TRISULFIDE;PROPYL TRITHIO PROPANE
• CAS NO: 6028-61-1
• Molecular Formula: C₆H₁₄S₃
• Molecular Weight: 182.37
• EINECS: 227-903-4
• Product Categories: sulfide Flavor
• Mol File: 6028-61-1.mol

Chemical Properties

• Boiling Point: 256.8 °C at 760 mmHg
• Flash Point: 106.1 °C
• Appearance: COA
• Density: 1.076 g/cm³
• Vapor Pressure: 0.0243mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 2-8°C
• BRN: 1736293
• CAS DataBase Reference: Dipropyl trisulfide(CAS DataBase Reference)
• NIST Chemistry Reference: Dipropyl trisulfide(6028-61-1)
• EPA Substance Registry System: Dipropyl trisulfide(6028-61-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• RTECS: UK3870000
• Hazardous Substances Data: 6028-61-1(Hazardous Substances Data)

Usage

Uses

1. Used in the Food Industry:
Dipropyl trisulfide is used as a flavoring agent for its strong garlic-like odor and taste, enhancing the flavor of various dishes and food products.
2. Used in the Agricultural Industry:
Dipropyl trisulfide is used as a preservative for cut potatoes, providing antibrowning and antimicrobial effects to maintain the quality and freshness of the produce.
3. Used in the Chemical Industry:
Dipropyl trisulfide can be utilized as a chemical intermediate for the synthesis of other organic compounds, taking advantage of its unique sulfur-containing structure.
4. Used in the Aromatherapy Industry:
Due to its strong and distinctive odor, Dipropyl trisulfide may be used in the formulation of aromatherapy products, potentially offering therapeutic benefits related to its scent.
5. Used in the Research and Development Industry:
Dipropyl trisulfide can be employed in research studies focusing on the properties and applications of sulfur-containing compounds, as well as their potential effects on various biological systems.

Preparation

By adaptation of Westlake’s procedure.

Synthesis Reference(s)

The Journal of Organic Chemistry, 22, p. 145, 1957 DOI: 10.1021/jo01353a011

InChI:InChI=1/C6H14S3/c1-3-5-7-9-8-6-4-2/h3-6H2,1-2H3

Upstream product

• 107-03-9 1-thiopropane 
• 624-92-0 Dimethyldisulphide 
• 629-19-6 Dipropyl disulfide 
• 61775-31-3 (disulfido)carbonic acid O-methyl ester SS-propyl ester 
• 54974-07-1 phthalimidesulfenyl chloride 
• 30912-77-7 N-(propyldithio)phthalimide 
• 107-08-4 1-iodo-propane 
• 106-94-5 propyl bromide 
• 66304-00-5 1-oxo-1H-1λ⁴-benzo[1,2]dithiol-3-one 
• 863478-22-2 7-chloro-1-oxo-1H-1λ⁴-benzo[1,2]dithiol-3-one 
• 863478-24-4 7-methoxy-1-oxo-1H-1λ⁴-benzo[1,2]dithiol-3-one 
• 863478-25-5 5-chloro-1-oxo-1H-1λ⁴-benzo[1,2]dithiol-3-one 
• 863478-26-6 5-methoxy-1-oxo-1H-1λ⁴-benzo[1,2]dithiol-3-one 
• 863478-23-3 7-methyl-1-oxo-1H-1λ⁴-benzo[1,2]dithiol-3-one 

Downstream Products

• 4154-77-2 hexaethyl-thiophosphamide 
• 629-19-6 Dipropyl disulfide 
• 534-25-8 1,2-dithiole-3-thione 
• 107-03-9 1-thiopropane 
• 111-47-7 propyl sulfide 
• 75030-40-9 benzyl n-propyl trisulfide 
• 27657-11-0 1-benzyl-2-propyldisulfane 
• 30453-31-7 ethyl propyl disulfide 
• 20195-06-6 O,O-diethyl-S-n-propyl phosporothiolate 

Relevant articles and documents

Key Odor-Active Compounds in Raw Green and Red Toona sinensis (A. Juss.) Roem. And Their Changes during Blanching

Application of aroma extract dilution analysis and headspace aroma dilution analysis revealed 51 odorants in raw green Toona sinensis and 54 odorants in raw red T. sinensis in the flavor dilution factor range of 8-4096. (E,E)-2,4-Decadienal, nonanal, 2,3,5-trimethylpyrazine, (E,Z)- and (Z,Z)-di-1-propenyl trisulfide, 2-methoxyphenol, and 4-ethylphenol were first identified as key odorants of T. sinensis. Clear differences between green and red T. sinensis in aroma profiles, flavor dilution factors, quantitative data, and odor activity values verified that (E,E)-, (E,Z)-, and (Z,Z)-di-1-propenyl disulfide, (E,E)-, (E,Z)- and (Z,Z)-di-1-propenyl trisulfide, cis- and trans-2-mercapto-3,4-dimethyl-2,3-dihydrothiophene, and dimethyl sulfide caused the distinct sulfury odor note of each variety. Further, hexanal, (E)-2-hexenal, (E)-2-hexen-1-ol, and (E,Z)-2,6-nonadienal led to the green odor note in green T. sinensis, while 2-methoxyphenol and 4-ethylphenol contributed to the intense phenolic aroma note in red T. sinensis. Quantitation experiments and triangle tests in blanched T. sinensis verified that the quick loss of the abovementioned sulfur-containing compounds, aldehydes, the alcohol (E)-2-hexen-1-ol, and phenols was responsible for the changes in the overall aroma profile during blanching.

Selectivity of diallyl trisulfides (DATS) in reducing HAuCl4 to produce gold nanoparticles: a detailed investigation

The bulbous root garlic (Allium sativum) with a strong taste and pungent odor is used widely in culinary preparations and folk medicine. Silver and gold nanoparticles (NPs) synthesized using this ingredient have also shown medicinal and therapeutic potency. Garlic contains organosulfur compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DATS). These compounds are of crucial significance as anticancer drugs. Reported here is a synthesis of a series of DATS with varying substituents and plausible application as capping as well as reducing agent to synthesize gold nanoparticles (TS-GNPs). In the process, it was discovered that among the selected DATs, only 1,3-di(but-1-ene)trisulfane could serve the purpose because of structural reasons. The reason for this intriguing selectivity has been investigated in detail using the experimental findings and theoretical calculations of the frontier molecular orbitals (FMO). Graphic abstract: Synthesis of a series of medicinally important symmetrical organic trisulfides as a structural analogue of diallyl trisulfides (DATS) in an attempt to construct organosulfur compound induced gold nanoparticles (GNPs), has been reported. Only 1,3-Di(but-1-ene)trisulfane in the lot is capable of reducing the chloroauric acid to synthesize the protected GNPs.[Figure not available: see fulltext.].

Trisulfides over disulfides: Highly selective synthetic strategies, anti-proliferative activities and sustained H2S release profiles

Temperature-and solvent-induced selective synthesis of trisulfides and disulfides is demonstrated. A remarkable selectivity was achieved using Na2S as a sulfur-Transfer agent under mild, greener, catalyst-free and additive-free conditions. This study reveals trisulfides as a better model than disulfides in general for a sustained release of H2S and potent anti-cancer activities.

Substituent effects on the reactivity of benzo-1,2-dithiolan-3-one 1-oxides and their possible application to the synthesis of DNA-targeting drugs

The efficiency of polysulfane product generation has been investigated for n-propyl thiol reactions with ortho- and para-substituted benzo-1,2-dithiolan-3- one 1-oxides in acetonitrile-water (7:3) mixtures. The reaction is facilitated by reducing the electron density at the para position or by placing substituents bearing lone pair electrons ortho to the dithiolanone-oxide (S1) reaction center. Through-space and through-bond effects both contribute to the conversion of polysulfane products.

Formation of dialkyl polysulfides from vinyl ethers in the system H2S-DMSO-MOH

The reaction of vinyl ethers with the system H2S-DMSO-MOH (30°C, 5 h) gives dialkyl polysulfides with a total yield of up to 65% instead of expected oxygen-containing thiols and sulfides. The ratio between dialkyl di-, tri-, and tetrasulfides depends on the nature of the vinyl ether and on the amount of alkali metal hydroxide in the reaction mixture. With di(propen-1-yl) ether, 4-methyl-2-ethyl-1,3-oxathiolane was also found as a by-product.

Use of a sacriflcial-sulfur electrode in electroorganic chemistry. V. Formation of the sequence CSSSC from S and thiols or thiolates

At a working potential of about +2.0 V (vs SCE) the carbon-sulfur electrode is a source of the electrogenerated cation S2+. In organic media, this electrophile reacts with thiols (or thiolates) to give a mixture of polysulfides of which the trisulfide is the main product. The reaction between electrogenerated Sy2- and alkyl halides is less selective. Elsevier,.

Reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide: Studies related to the reaction of antitumor antibiotic leinamycin with DNA

We have studied the reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide. The major products isolated from these reactions are the corresponding dithio carboxylic acids. In the case of 3H-1,2-benzodithiol-3-one 1-oxide, an unstable hydrodisulfide that decomposes to polysulfides under the reaction conditions is formed. A mechanism involving an unstable oxathiolanone intermediate is proposed for these reactions. We believe that these reactions may serve as useful models for some aspects of the thiol-activated DNA-cleavage chemistry of the antitumor antibiotic leinamycin, a natural product that contains a 1,2-dithiolan-3-one 1-oxide heterocycle.