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Dimethyl trisulfide

Dimethyl trisulfide is a volatile organosulfur compound with the molecular formula C₂H₆S₃, consisting of two methyl groups linked by a trisulfide chain (CH₃–S–S–S–CH₃), making it the simplest organic trisulfide.^[1] It is characterized by a strong, diffusive, and penetrating odor reminiscent of fresh onion and garlic, often described as sulfurous, alliaceous, and savory.^[2]^[3] This compound occurs naturally in various foods and biological materials, including Allium vegetables such as garlic and onion, Brassica species like broccoli and cabbage, as well as coffee, cocoa, cheeses, meats, and even human urine.^[2]^[3]^[4] It forms during the breakdown of sulfur-containing amino acids and contributes significantly to the pungent aroma and flavor profiles of these sources, particularly when cooked or crushed.^[3]^[4] Physically, dimethyl trisulfide appears as a clear yellow liquid with a melting point of -68 °C, a boiling point of approximately 170 °C at atmospheric pressure, and a density of 1.202 g/mL at 25 °C.^[5]^[2] It exhibits low solubility in water but good solubility in alcohols, propylene glycol, and oils, and it is flammable with a flash point around 56 °C.^[2]^[5] In practical applications, it serves as a flavor and fragrance agent in food products like baked goods, soups, meats, and dairy, approved by FEMA for use at low concentrations (up to 1 ppm).^[3] Additionally, it has been explored for uses in pest control as a trap bait for blowflies and shows potential pharmacological effects, such as acting as a cyanide antidote in animal models, inhibiting adipocyte formation in preliminary anti-obesity studies, and recent investigations into its anti-inflammatory effects and antifungal activity against pathogens like Aspergillus flavus.^[2]^[4]^[6]^[7] Safety-wise, it is classified as harmful if swallowed, causing skin and eye irritation, and requires handling precautions due to its flammability and strong odor.^[2]

Structure and Properties

Molecular Structure

Dimethyl trisulfide, the simplest organic trisulfide, has the molecular formula C_2H_6S_3, consisting of two methyl groups bridged by a chain of three sulfur atoms.^[1] Its IUPAC name is dimethyltrisulfane, with systematic alternatives including 2,3,4-trithiapentane and common synonyms such as methyltrisulfanylmethane. The structural formula is CH_3-S-S-S-CH_3, featuring a linear trisulfide chain where the central sulfur atom is bonded to two terminal sulfurs, each further connected to a methyl group.^[1] The molecule adopts a linear chain conformation around the S-S-S linkage, with the two S-S bonds exhibiting lengths of approximately 2.05 Å, characteristic of polysulfide linkages.^[8] This bond length is comparable to the S-S bond in the simpler analog dimethyl disulfide (CH_3SSCH_3), which measures about 2.03–2.07 Å, reflecting similar covalent bonding in these organosulfur compounds.^[9] Computational studies confirm these dimensions, highlighting the stability of the trisulfide chain without significant deviation from disulfide geometry.^[10] Spectroscopic techniques provide definitive confirmation of the structure. In the ^1H NMR spectrum, the equivalent methyl protons resonate at approximately 2.55 ppm (singlet), deshielded relative to dimethyl disulfide (2.41 ppm) due to the extended sulfur chain.^[11] Infrared spectroscopy reveals characteristic S-S stretching vibrations around 500 cm^{-1}, typical for the trisulfide moiety and distinguishing it from C-S stretches near 700 cm^{-1}.^[12] These vibrational modes underscore the localized bonding in the S-S-S unit, with minimal coupling to the methyl groups.

Physical Properties

Dimethyl trisulfide is a pale yellow to yellow liquid at room temperature, characterized by its powerful, diffusive odor reminiscent of garlic or onion, often described as alliaceous.^[1]^[2] This distinctive smell arises from its volatile nature and is detectable at very low concentrations.^[2] Key physical properties of dimethyl trisulfide under standard conditions are summarized in the following table:

Property	Value	Conditions/Source
Density	1.202 g/mL	25 °C [lit.]^[2]
Melting point	-68 °C	[lit.]^[2]
Boiling point	170 °C; 58 °C	760 mmHg; 15 mmHg [lit.]^[13]^[2]
Refractive index	1.602	20 °C [lit.]^[2]
Solubility	Insoluble in water; soluble in alcohols, propylene glycol, oils, ethanol, ether, and chloroform	[JECFA]^[1]^[2]

The compound is flammable, with a flash point of approximately 56 °C, and upon combustion, it produces carbon monoxide, carbon dioxide, and sulfur oxides.^[13]^[14] The low melting point can be attributed briefly to the flexibility of the S-S-S chain in its molecular structure, contributing to reduced intermolecular forces.^[15]

Occurrence

In Nature

Dimethyl trisulfide (DMTS) is emitted as a volatile compound by various Allium species, including wild garlic (Allium ursinum) and wild leeks, particularly under conditions of plant stress such as mechanical damage or pathogen infection, as well as during tissue decomposition.^[16]^[17] In wild garlic, DMTS constitutes a significant portion of the volatile oil profile, reaching up to 12% in leaves and 9.7% in flowers, contributing to the plant's characteristic sulfurous aroma released upon cellular disruption.^[16]^[17] In microbial processes, DMTS is produced by anaerobic bacteria during the degradation of organic matter in soils, sewage systems, and decaying plant material, where it contributes to the characteristic rotten egg odors associated with sulfur volatilization.^[18]^[19] Sulfate-reducing bacteria and other anaerobes facilitate this production through the breakdown of sulfur-containing compounds, with DMTS often detected in wastewater sludge headspaces as decomposition progresses.^[20]^[21] DMTS occurs as a volatile compound in certain fungi, notably truffles (Tuber species) and mushrooms such as shiitake (Lentinula edodes), where it forms part of the fruiting body's aroma profile.^[22]^[23] In Chinese truffle varieties like Tuber sinensis and Tuber sinoexcavatum, DMTS concentrations range from 5.57 to 7.52 μg/kg, imparting garlic-like notes to the scent.^[22] Its presence in truffle microbiomes suggests contributions from associated bacteria and fungi during fruitbody development.^[24] Ecologically, DMTS serves as a defense compound against pathogens, exhibiting broad-spectrum antifungal activity that inhibits mycelial growth and spore germination in fungi such as Alternaria alternata and Colletotrichum gloeosporioides.^[7]^[25] In plants and microbes, it acts as a signaling molecule, priming stress responses and interspecies communication, while participating in sulfur cycling through the degradation of amino acids like methionine by soil bacteria.^[26]^[24] This volatile facilitates nutrient recycling in anaerobic environments, linking organic matter breakdown to atmospheric sulfur flux.^[18] In natural waters and soils, DMTS occurs at trace levels, typically in the parts-per-billion (ppb) range, associated with anaerobic bacterial activity in eutrophic or decaying systems.^[27]^[20] Concentrations in lake waters and wetland soils can reach 0.1–2.7 ppbv in headspace emissions, reflecting low-level production during microbial sulfur metabolism.^[28]^[29]

In Food and Beverages

Dimethyl trisulfide is a key volatile sulfur compound released from Allium vegetables such as onions, garlic, and leeks upon cutting or cooking, contributing pungent, sulfurous, and cooked onion-like aromas to these foods.^[30] In fresh garlic, concentrations are relatively low at approximately 2 μg/g, but levels increase significantly during thermal processing due to the enzymatic breakdown of precursors like S-methyl-L-cysteine sulfoxide into polysulfides.^[30] For instance, in cooked onions, dimethyl trisulfide can reach up to 147 μg/g, enhancing the savory and garlicky profiles characteristic of stir-fried or boiled preparations.^[30] In cruciferous vegetables like broccoli and cabbage, dimethyl trisulfide forms during thermal processing or fermentation, imparting sulfurous, fishy, and cabbage-like notes that can border on off-flavors if overcooked.^[31] It arises from the degradation of S-methyl-L-cysteine sulfoxide, with detectable levels in cooked broccoli florets and fermented cabbage products such as sauerkraut, where it is among the most abundant sulfur volatiles contributing to the overall fermented aroma.^[32]^[33] Beyond vegetables, dimethyl trisulfide enhances savory and garlicky flavors in fermented and aged foods, including hard cheeses like Cheddar and Parmesan, where it derives from methionine degradation and imparts ripe cheese and garlic notes at concentrations around 0.007–0.03 mg/kg.^[34]^[31] In wines, it serves as a potent odorant influencing subtle sulfurous undertones, while in sauerkraut, it bolsters the cabbage-like profile during lactic acid fermentation.^[35]^[33] The compound's low odor detection threshold of approximately 0.001 ppm in air underscores its sensory impact, allowing even trace amounts to significantly shape the volatile sulfur profile of these consumables.^[31]

Biosynthesis and Synthesis

Biosynthesis

Dimethyl trisulfide (DMTS) is biosynthesized in plants primarily through the enzymatic cleavage of S-methyl-L-cysteine sulfoxide (SMCSO), a non-protein amino acid precursor abundant in Brassica and certain Allium species. Upon mechanical tissue damage, such as during harvesting or herbivore attack, the enzyme cysteine sulfoxide lyase (also known as alliinase in Allium plants) hydrolyzes SMCSO to yield methyl sulfenic acid, ammonia, and pyruvate. The unstable methyl sulfenic acid then spontaneously condenses, either with itself to form methyl methanethiosulfinate or with methanethiol to produce dimethyl disulfide (DMDS), which further reacts to generate DMTS as a trisulfide derivative. This pathway is analogous to the formation of allyl-based trisulfides from alliin in garlic, where similar sulfenic acid intermediates lead to organosulfur volatiles upon alliinase activation.^[36]^[37] In microbial systems, particularly anaerobic bacteria such as Pseudomonas species, DMTS arises from the degradation of sulfur-containing amino acids like methionine and cysteine through distinct enzymatic steps involving transsulfuration and methylation. Methionine gamma-lyase (MGL), a pyridoxal phosphate-dependent enzyme, catalyzes the breakdown of L-methionine to methanethiol (CH3SH), α-ketobutyrate, and ammonia under anaerobic conditions. Similarly, cysteine desulfhydrase cleaves L-cysteine to hydrogen sulfide (H2S), pyruvate, and ammonia, with subsequent methylation of H2S yielding methanethiol via S-adenosylmethionine-dependent methyltransferases. The resulting methanethiol then condenses with elemental sulfur or oxidized intermediates like DMDS to form DMTS, often as part of volatile sulfur compound (VSC) production during amino acid catabolism.^[38]^[39]^[40] Biosynthesis of DMTS is tightly regulated in both plants and microbes to respond to environmental cues. In plants, the pathway is induced by oxidative stress or pathogen attack, enhancing the production of DMTS and related VSCs as antimicrobial defense signals that deter herbivores and inhibit microbial pathogens. Microbial production, conversely, is influenced by pH and temperature, with optimal DMTS yields occurring under mildly acidic (pH 5-7) and mesophilic (25-37°C) conditions that favor enzyme activity and anaerobic metabolism.^[41]^[42]^[40] Yield of DMTS precursors and thus the compound itself in Allium plants is significantly enhanced in sulfur-rich soils, where elevated sulfate availability boosts the accumulation of SMCSO and other S-alk(en)yl-L-cysteine sulfoxides via upregulated sulfate assimilation pathways. For instance, garlic grown in soils amended with 30-60 kg/ha elemental sulfur exhibits higher concentrations of organosulfur volatiles, including those derived from methyl precursors.^[43]^[44]

Chemical Synthesis

Dimethyl trisulfide is primarily synthesized in the laboratory by the copper(II)-catalyzed reaction of methanethiol with hydrogen sulfide, which produces the symmetrical trisulfide along with hydrogen gas.

$2 \ \ce{CH3SH} + \ce{H2S} \rightarrow \ce{CH3SSSCH3} + 2 \ \ce{H2}

This redox process occurs efficiently in hydroalcoholic solutions at ambient temperatures, mimicking conditions relevant to food chemistry but adaptable for synthetic purposes.^[45] An established alternative method employs sulfur dichloride as a sulfur source, reacting two equivalents of methanethiol with the reagent to generate dimethyl trisulfide and hydrochloric acid.

$2 \ \ce{CH3SH} + \ce{SCl2} \rightarrow \ce{CH3SSSCH3} + 2 \ \ce{HCl}

The reaction is typically performed at low temperatures ranging from -10 to 25 °C in an inert solvent to suppress thermal decomposition of the product. This approach is a standard route for preparing symmetrical trisulfides from thiols. Additional synthetic routes can produce dimethyl trisulfide as a byproduct during the oxidation of dimethyl disulfide with elemental sulfur in processes aimed at disulfide production.^[46] Due to its high volatility and low boiling point (approximately 170 °C at atmospheric pressure), dimethyl trisulfide is purified by vacuum distillation, often under reduced pressure (10-20 mmHg) to isolate the pure compound.

Chemical Reactions

Oxidation and Decomposition

Dimethyl trisulfide (DMTS) undergoes abiotic decomposition under dark, oxic conditions primarily through a base-catalyzed disproportionation mechanism involving hydroxyl ions, leading to the initial formation of dimethyl disulfide (DMDS, Me₂S₂) and higher polysulfides such as dimethyl tetrasulfide (Me₂S₄) and dimethyl pentasulfide (Me₂S₅). Over longer timescales, the apparent final products are DMDS and elemental sulfur (S). This process is second-order with respect to DMTS concentration and exhibits a partial first-order dependence on OH⁻ concentration, with an activation energy of approximately 170 kJ mol⁻¹. In natural aquatic environments like Lake Kinneret, the half-life of DMTS is estimated at around 100,000 years under typical conditions, indicating high stability against slow oxidation by dissolved oxygen. Laboratory storage studies confirm this stability, showing no measurable degradation of DMTS in air-exposed formulations at 4 °C and 22 °C over 12 months, though exposure to elevated temperatures (37 °C) results in up to 70% loss after 12 months, with DMDS as a primary degradation product alongside higher polysulfides. Controlled oxidation experiments using peroxides like hydrogen peroxide (H₂O₂) or meta-chloroperoxybenzoic acid (mCPBA) accelerate the process, yielding higher polysulfides as intermediates and S-methyl methanethiosulfonate in the case of mCPBA. Thermal decomposition of DMTS occurs at elevated temperatures, with significant breakdown observed at 150 °C over 48 hours in micellar solutions, producing methanethiol (CH₃SH), hydrogen sulfide (H₂S), and carbon disulfide (CS₂) as major products. This aligns with the compound's volatility and sulfur chain instability under heat, though surface-catalyzed reactions on metals like gold (Au(111)) at 200–300 K instead favor coupling to DMDS and atomic sulfur without detectable CH₃SH, H₂S, or CS₂. The decomposition rate increases with temperature, contributing to odor evolution in heated systems, but DMTS remains intact below 100 °C for extended periods. DMTS exhibits good stability in neutral to mildly acidic conditions, showing no degradation in micellar solutions across pH 2.6–7.0 over short exposures (15 minutes). No evidence of hydrolysis to thiols or polysulfanes (H-Sₙ-H species) was observed in strong acids under tested conditions, consistent with its persistence in aqueous formulations. Photolytic degradation pathways remain underexplored, with limited data suggesting potential S-S bond cleavage under UV irradiation, but no confirmed production of radicals or thiols in isolated studies.

Sulfur Donor Reactions

Dimethyl trisulfide (DMTS) serves as an effective sulfur donor in the enzymatic detoxification of cyanide, primarily through its interaction with the enzyme rhodanese (thiosulfate sulfurtransferase). In this process, DMTS transfers a sulfur atom to rhodanese, which then catalyzes the conversion of cyanide (CN⁻) to the less toxic thiocyanate (SCN⁻), following the simplified reaction:

(\ce{CH3})_2\ce{S3} + \ce{CN^-} \rightarrow (\ce{CH3})_2\ce{S2} + \ce{SCN^-}

This mechanism enhances the natural detoxification pathway, with DMTS demonstrating superior efficacy compared to traditional sulfur donors like sodium thiosulfate, achieving over 40-fold higher conversion rates in vitro at physiological pH when rhodanese is present.^[47]^[48] The sulfur transfer rate of DMTS to cyanide is approximately 10 times faster than that of dimethyl disulfide, attributed to the additional sulfur atom in the trisulfide chain facilitating nucleophilic attack by the cyanide ion on the terminal S-S bond. Kinetic studies reveal that this reaction proceeds via two pH-dependent pathways: a slower protonated cyanide mechanism under acidic or neutral conditions and a faster cyanide anion pathway under alkaline conditions, with overall half-lives ranging from months to millennia depending on environmental factors. Even without rhodanese, DMTS directly reacts with free cyanide to form thiocyanate, underscoring its versatility as a donor.^[49]^[50] In biological systems, DMTS also interacts with hemoglobin, oxidizing it to methemoglobin, which binds free cyanide and contributes to the antidote mechanism by preventing cellular hypoxia. This oxidation alters the hemoglobin absorption spectrum, similar to the action of sodium nitrite, though at a slower rate; the process involves sulfur transfer leading to ferric iron formation without evidence of sulfhemoglobin complexation. Such interactions highlight DMTS's dual role in both enzymatic sulfur donation and direct heme protein modification for cyanide neutralization.^[51] Beyond cyanide contexts, DMTS undergoes S-S bond cleavage via nucleophilic attacks from species like thiols and amines, yielding sulfides, persulfides, and disulfides. For instance, reaction with glutathione proceeds through thiol-disulfide exchange, rapidly releasing hydrogen sulfide and forming oxidized glutathione dimers, which demonstrates the compound's reactivity in generating bioactive persulfides under physiological conditions. These cleavages typically target the labile terminal S-S bonds, enabling controlled sulfur transfer in nucleophilic environments.^[52] In organic synthesis, DMTS is employed to introduce -S-S-S- linkages into molecules via metathesis reactions in polar aprotic solvents like dimethylformamide or pyridine. For example, mixing DMTS with other trisulfides or thiols promotes S-S exchange, forming unsymmetric trisulfides such as benzyl methyl trisulfide, providing a mild route to polysulfide-containing compounds without radical intermediates. This approach has been applied to construct biologically relevant trisulfide motifs, leveraging DMTS's stability and selective bond reactivity.^[53]^[54]

Uses

Flavoring Agent

Dimethyl trisulfide is recognized as a generally recognized as safe (GRAS) flavoring substance by the Flavor and Extract Manufacturers Association (FEMA) under number 3275, serving as a flavor enhancer to impart savory and alliaceous notes in processed foods such as meats, soups, and snacks.^[55] Its characteristic sulfurous, onion-like profile mimics natural garlic and onion aromas, which occur in these foods, but it is primarily synthesized for industrial applications to ensure consistency and scalability in flavor packets.^[3] In food formulations, dimethyl trisulfide is typically incorporated at low concentrations of 0.1 to 10 ppm to replicate alliaceous flavors without overpowering other ingredients; for example, levels around 20 ppm enhance cooked onion realism, while 5 ppm adds depth to roast beef profiles.^[56] This usage contributes to the overall sulfur volatile component in seasoning blends, supporting authentic savory notes in products like gravies and condiments at average maximum levels of 1 ppm.^[3] The compound's sensory profile features a gassy, meaty, and vegetative nuance that bolsters umami perception and pungency, as seen in its role in enhancing the aftertaste of fermented foods like soy miso, while avoiding bitter off-notes.^[57] In fragrance applications, it functions as an agent for diffusive, alliaceous scents in select formulations, leveraging its stability in ethanol-based media for perfumes and related products.^[3]

Medical and Pharmaceutical Applications

Dimethyl trisulfide (DMTS) has been investigated as a promising cyanide antidote due to its role as a sulfur donor, which facilitates the enzymatic conversion of cyanide to the less toxic thiocyanate via sulfurtransferase enzymes such as rhodanese.^[58] In animal models, DMTS demonstrates high efficacy at low doses, such as 12.5–50 mg/kg administered subcutaneously, intramuscularly, or intravenously, achieving survival rates of up to 92% in mice exposed to lethal cyanide levels.^[59] Compared to traditional agents like sodium thiosulfate, DMTS exhibits faster onset of action and greater efficiency, with in vitro conversion rates over 40 times higher in the presence of rhodanese and approximately 80 times higher without it, leading to antidotal protection ratios of 3.3–3.73 versus 1.1 for thiosulfate at equivalent 100 mg/kg doses in mice.^[60] In a large swine model of severe cyanide poisoning, intramuscular DMTS improved survival to 83% versus 0% in controls and reduced recovery time to normal breathing to about 19 minutes.^[61] DMTS also displays antifungal properties, inhibiting spore germination and mycelial growth in pathogenic fungi relevant to human health, such as Aspergillus flavus and Botryosphaeria dothidea.^[62] Against A. flavus, a producer of carcinogenic aflatoxins, DMTS at 50 μL/L concentrations significantly suppresses conidial germination by targeting acetyl-CoA carboxylase (ACC), an enzyme essential for fungal fatty acid synthesis and toxin production, thereby downregulating ACC gene expression and activity.^[62] Similarly, DMTS at 62.5–250 μL/L fully inhibits mycelial growth of B. dothidea in vitro and reduces disease incidence by 97% on postharvest apple fruits at 15.63 μL/L, suggesting potential for development as an antifungal therapeutic or preservative in pharmaceutical formulations for infection control.^[63] In preclinical studies, DMTS exerts anti-inflammatory and analgesic effects, particularly in models of neuropathic pain induced by partial sciatic nerve ligation in mice.^[64] Administered at approximately 30–50 mg/kg intraperitoneally, DMTS restores mechanical pain thresholds to baseline levels by activating transient receptor potential ankyrin 1 (TRPA1) channels on sensory neurons, which triggers somatostatin release and modulates downstream anti-nociceptive pathways via somatostatin receptor 4 (SST4).^[64] This TRPA1-dependent mechanism reduces microglial activation in the spinal cord dorsal horn and alleviates hyperalgesia without affecting healthy pain thresholds, highlighting its selectivity for pathological states.^[64] Emerging research post-2020 indicates neuroprotective potential for DMTS against oxidative stress, with preclinical evidence supporting its application in conditions like arthritis and stress-related disorders. In a mouse model of gouty arthritis, DMTS at 50 mg/kg intraperitoneally reduced joint swelling, oxidative markers such as malondialdehyde, and proinflammatory cytokines while preserving vascular integrity, demonstrating antioxidant and anti-inflammatory benefits.^[65] Additionally, DMTS has shown anxiolytic and antidepressant effects in acute stress models by mitigating oxidative damage and activating TRPA1-mediated pathways, suggesting broader neuroprotective roles in trauma or neurodegeneration, though human trials are lacking.^[66] The lipophilic nature of DMTS poses formulation challenges for pharmaceutical applications, as its aqueous solubility is limited to 0.13 mg/mL, necessitating delivery systems like emulsions, micelles, or co-solvent mixtures with surfactants (e.g., polysorbates at 1–50% w/w) and cyclodextrins to enable effective intravenous or intramuscular administration.^[59] Its recognition as generally recognized as safe (GRAS) by the Flavor and Extract Manufacturers Association for oral use further supports its safety profile in therapeutic contexts.^[1]

Pest Control

Dimethyl trisulfide has been explored for use in pest control, particularly as a trap bait to attract blowflies for monitoring and management in forensic and agricultural contexts.^[2]

Safety and Toxicology

Health Hazards

Dimethyl trisulfide acts as an irritant to skin and eyes upon direct contact, potentially causing redness, burning sensations, and serious eye damage.^[67] Inhalation of its vapors may lead to respiratory tract irritation, manifesting as coughing, throat discomfort, and possible shortness of breath.^[67] Ingestion can result in gastrointestinal disturbances, including nausea and vomiting, with an acute oral LD50 value of approximately 500 mg/kg in rats.^[67] Limited toxicity data exist for inhalation exposure, but the compound's volatility contributes to risks from airborne vapors, potentially causing headaches and a persistent garlic-like odor on the breath due to its characteristic scent.^[67] No specific LC50 values for rats were identified in available safety assessments.^[67] Chronic exposure data are scarce, with no established evidence of carcinogenicity; dimethyl trisulfide is not classified by the International Agency for Research on Cancer (IARC).^[67] As a flammable liquid with a flash point around 56°C, dimethyl trisulfide vapors can ignite readily and form explosive mixtures with air, especially at elevated temperatures; combustion produces hazardous fumes including carbon oxides.^[67] Individuals with asthma or sensitivities to sulfur-containing compounds are particularly vulnerable to its respiratory irritant effects.^[67]

Regulatory Status

Dimethyl trisulfide is affirmed as generally recognized as safe (GRAS) for use as a synthetic flavoring agent in food by the Flavor and Extract Manufacturers Association (FEMA) under GRAS number 3275, as a GRAS substance for use in food under good manufacturing practices, as recognized by the U.S. Food and Drug Administration (FDA). FEMA guidelines specify average and maximum use levels of 1 ppm in non-alcoholic beverages, among other food categories, to ensure safety. In the European Union, dimethyl trisulfide is approved as a flavoring substance under Regulation (EC) No 1334/2008 on flavorings and food ingredients with flavoring properties, and it is included in the EU flavorings inventory per Commission Regulation (EC) No 1565/2000, without an assigned E-number as is typical for flavorings.^[3] No specific permissible exposure limit (PEL) has been established by the Occupational Safety and Health Administration (OSHA) for dimethyl trisulfide; however, for analogous sulfur compounds such as dimethyl disulfide, the American Conference of Governmental Industrial Hygienists (ACGIH) recommends a threshold limit value of 0.5 ppm as an 8-hour time-weighted average (TWA), with skin notation due to potential absorption. For transport, dimethyl trisulfide is designated UN 1993, flammable liquid, n.o.s., under Class 3 (flammable liquids), packing group III, with applicable Globally Harmonized System (GHS) hazard statements including H226 (Flammable liquid and vapour), H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation).^[68] Due to its respiratory irritant properties, adequate ventilation is advised during occupational handling.^[68]

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Sep 19, 2022 · The most important odorants in garlic were di(2-propenyl)disulfide and di(2-propenyl)trisulfide. In leek, compounds possessing leek aroma were ...Missing: wild | Show results with:wild
[32]
Microbial Community Dynamics and Metabolome Changes During ...
Especially, dimethyl disulfide and dimethyl trisulfide were the most abundant sulfur-containing compounds, which contributed a cabbage-like odor and had been ...
[33]
Key aroma compounds identified in Cheddar cheese with different ...
Dimethyl trisulfide also contributes significantly to the aroma of Gruyere cheese (Curioni and Bosset, 2002) and is generally associated with odor notes of ...Missing: sauerkraut | Show results with:sauerkraut
[34]
Flavor Chemistry of Wine and Other Alcoholic Beverages
Flavor Chemistry of Wine and Wine Grape. Assessing Smoke ... On the basis of odor activity values (OAVs), the most potent odorants were dimethyl trisulfide.
[35]
S‐Methyl‐l‐Cysteine Sulfoxide: A Hidden Layer of Defences Against ...
Sep 12, 2025 · Enzymatic hydrolysis of S‐methyl‐l‐cysteine sulfoxide (SMCSO) leading to the formation of volatile organic compounds, i.e., dimethyldisulfide ( ...
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Formation of volatile sulfur compounds and S-methyl-l-cysteine ...
Jul 30, 2022 · S-Methyl methanethiosulfinate was the main VOSC released from SMCSO. Upon heating, it degraded to dimethyltrisulfide and dimethyldisulfide, ...
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S-Methylcysteine sulfoxide in Brassica vegetables and formation of ...
S-Methylcysteine sulfoxide in Brassica vegetables and formation of methyl methanethiosulfinate from Brussels sprouts | Journal of Agricultural and Food ...
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Identification and Functional Analysis of the Gene Encoding ... - NIH
The disruption of the mgl gene, achieved in strain ATCC 9175, resulted in a 62% decrease in thiol-producing activity and a 97% decrease in total VSC production ...Materials And Methods · Dna Techniques · Results
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Properties of L-methionine γ-lyase from Pseudomonas ovalis
Evaluation of Methanethiol and Hydrogen Sulfide Production by Standard Strains of Intestinal Bacteria and Isolates from Pig Feces. Bioscience and Microflora ...Missing: trisulfide | Show results with:trisulfide
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The effect of cysteine on production of volatile sulphur compounds ...
Mar 20, 2008 · Chin and Lindsay (1994) proposed that hydrogen sulphide (H2S), the main product of cysteine catabolism, is involved in DMTS and DMQS formation.
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The Versatile Roles of Sulfur-Containing Biomolecules in Plant ...
Sulfur (S) is an essential plant macronutrient and the pivotal role of sulfur compounds in plant disease resistance has become obvious in recent decades.
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Microbial pathways in colonic sulfur metabolism and links ... - Frontiers
Nov 27, 2012 · Cysteine desulfhydrase is a key enzyme for initial microbial cysteine fermentation and pyruvate production. However, recent evidence ...
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Selenium and Sulfur to Produce Allium Functional Crops - PMC - NIH
In Allium crops grown in soils low in organic matter (< 1%) it is advisable to provide elemental sulfur applied to the soil (30–60 kg·ha−1) in addition to the ...
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Selenium and Sulfur to Produce Allium Functional Crops - MDPI
The amino acids cysteine and selenocysteine are the starting point of various metabolic pathways such as the formation of dimethyldisulfide by the methylation ...
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Hydrogen Sulfide Reactivity with Thiols in the Presence of Copper(II) in Hydroalcoholic Solutions or Cognac Brandies: Formation of Symmetrical and Unsymmetrical Dialkyl Trisulfides
### Summary of Chemical Reaction (Hydrogen Sulfide, Methanethiol, and Copper(II) to Dimethyl Trisulfide)
[46]
Stability Characterization of a Polysorbate 80-Dimethyl Trisulfide ...
A lead candidate compound is dimethyl trisulfide (DMTS), which acts as a sulfur donor for rhodanese, thereby assisting the conversion of cyanide into ...
[47]
Dimethyl trisulfide: A novel cyanide countermeasure - Sage Journals
sulfur donor-type cyanide antidotes when applied ... dimethyl trisulfide as a cyanide antidote. US ... intercalated rhodanese in cyanide antagonism. Nano ...
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Cyanide antidote compositions and methods of use - Google Patents
It was unexpectedly found that sodium cyanide was converted to SCN least 10 times faster ... Dimethyl trisulfide as a cyanide antidote. WO2015157752A1 ...
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Kinetics and mechanism of the reaction between dimethyl trisulfide ...
Mar 25, 2021 · In this work, the reaction kinetics of dimethyl trisulfide (DMTS) with the strong nucleophile and important environmental pollutant cyanide as a ...
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Reaction of Dimethyl Trisulfide with Hemoglobin
### Summary of Mechanism from https://pubs.acs.org/doi/10.1021/acs.chemrestox.7b00181
[51]
Stabilities of Three Key Biological Trisulfides with Implications for ...
Mar 22, 2022 · When trisulfides react with thiols, they yield persulfides (2−5) that are stronger nucleophiles than thiols, which makes them more reactive ...Missing: hydrolysis | Show results with:hydrolysis
[52]
[PDF] Spontaneous Trisulfide Metathesis in Polar Aprotic Solvents
Furthermore, the proradical spin trap 5,5-dimethyl-1- pyrroline-N-oxide (DMPO) did not react with dimethyl trisulfide in DMF and no radicals were detected ...
[53]
Chemically induced repair, adhesion, and recycling of polymers ...
May 15, 2020 · (b) Tribu- tylphosphine mediates rapid S–S metathesis and desulfurization of dimethyl trisulfide and di-n-propyl trisulfide at 20 C. (c) ...
[54]
DIMETHYL TRISULFIDE | FEMA
Dimethyl trisulfide (FEMA #3275) has a flavor profile of cabbage, fish, onion, and sulfur. Its CAS number is 3658-80-8.
[55]
Flavor Bites: Dimethyl trisulfide | Perfumer & Flavorist
Mar 22, 2018 · Added to this, there are dramatic variations in strength, dimethyl trisulfide is many hundreds of times stronger than dimethyl sulfide.Missing: fungi mushrooms
[56]
Analysis of the cooked aroma and odorants that contribute to umami ...
Dec 15, 2016 · Dimethyl trisulfide, one of the odorants of soy miso, contributes to the taste. •. Our findings will contribute to the control of the umami ...
[57]
DMTS is an effective treatment in both an inhalation and injection ...
Sep 19, 2017 · Dimethyl trisulfide (DMTS), Span 80, and Tween 80 were obtained from ... This study demonstrates that DMTS is an effective cyanide antidote in a ...
[58]
Formulations of dimethyl trisulfide for use as a cyanide antidote
Dimethyl trisulfide antidote compositions may be used to as a cyanide poisoning antidote. Formulations of dimethyl trisulfide may be made in an aqueous ...<|separator|>
[59]
Dimethyl trisulfide: A novel cyanide countermeasure - PubMed
In the present studies, the in vitro and in vivo efficacies of a novel cyanide countermeasure, dimethyl trisulfide (DMTS), were evaluated ... sulfur donor-type ...
[60]
Evaluation of aqueous dimethyl trisulfide as an antidote to a highly ...
Jun 18, 2021 · ... dimethyl trisulfide (DMTS) on survival and clinical outcomes ... Keywords: Cyanide; antidote; dimethyl trisulfide; swine. Publication ...
[61]
Acetyl-CoA carboxylase as potential molecular target of dimethyl ...
Apr 15, 2024 · Acetyl-CoA carboxylase (ACC) is key for A. flavus growth and aflatoxin production. •. Dimethyl trisulfide (DMTS) reduced the ACC activity, down- ...
[62]
Efficacy of Dimethyl Trisulfide on the Suppression of Ring Rot ... - NIH
Feb 7, 2022 · DT inhibited apple ring rot on postharvest fruit by suppressing the growth of B. dothidea, and inducing the defense-related genes in apple fruit.
[63]
Dimethyl Trisulfide Diminishes Traumatic Neuropathic Pain Acting ...
Mar 25, 2021 · Dimethyl Trisulfide Alleviates Neuropathic Pain. Neither DMTS nor respective vehicle treatment had any effect on the mechanical pain threshold ...
[64]
The anti-inflammatory effect of dimethyl trisulfide in experimental ...
Oct 5, 2023 · ... oxidative stress, and we demonstrated that DMTS is a sulfur donor ... dimethyl trisulfide on vascular and histological changes in serum-transfer arthritis.
[65]
Anxiolytic and Antidepressant Effects of Organic Polysulfide ...
Jun 14, 2025 · Background/Objectives: Dimethyl trisulfide (DMTS) is a naturally occurring polysulfide with known antioxidant and neuroprotective properties.
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https://pubmed.ncbi.nlm.nih.gov/40574094/
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Substance Information - ECHA
### Summary of Dimethyl Trisulphide (EC: 222-910-9, CAS: 3658-80-8)