Ethyl methyl disulfide

• CAT Number: R090011
• CAS Number: 20333-39-5
• PubChem Substance ID: 123388
• Molecular Formula: C3H8S2
• Molecular Weight: 108.23
• Purity: ≥95%
• IUPAC Name: (methyldisulfanyl)ethane
• InChI: InChI=1S/C3H8S2/c1-3-5-4-2/h3H2,1-2H3
• InChIKey: XLTBPTGNNLIKRW-UHFFFAOYSA-N
• SMILES: CCSSC

Ethyl methyl disulfide (Cat.No:R090011) is a sulfurous and truffle tasting compound. Outside of the human body, ethyl methyl disulfide is found, on average, in the highest concentration in kohlrabis.

Reference

[1]. Chem Phys Lipids. 1996 Nov 1;84(1):81-5. doi: 10.1016/s0009-3084(96)02625-4.
Dimethyl disulfide derivatization of ethyl (9Z,12Z)-9, 12-octadecadienoate and ethyl (9E,12E)-9,12-octadecadienoate.
Carballeira NM(1), Cruz C.
Author information: (1)Department of Chemistry, University of Puerto Rico, San Juan 00931-3346.
The dimethyl disulfide derivatization of ethyl (9Z,12Z)-9,12-octadecadienoate and ethyl (9E,12E)-9,12-octadecadienoate was studied. These methylene-interrupted dienes were reacted with dimethyl disulfide and I2 for 72 h at 50 degrees C and the tetrahydrothiopyran, thietane, and tetrahydrothiophene derivatives thus obtained were analyzed by gas chromatography-mass spectrometry. Each configurational isomer displayed a unique gas chromatography trace for the 4-, 5- and 6-membered ring cyclization products thus obtained. Therefore, the cis-cis and trans-trans double bond stereochemistry of 9,12-octadecadienoates can now be determined by dimethyl disulfide derivatization.
DOI: 10.1016/s0009-3084(96)02625-4 PMID: 8952054 [Indexed for MEDLINE]

[2]. Chem Biodivers. 2015 Sep;12(9):1415-21. doi: 10.1002/cbdv.201400342.
Effect of volatile organic compounds from bacteria on nematodes.
Xu YY(1), Lu H(1), Wang X(1), Zhang KQ(2), Li GH(3).
Author information: (1)Laboratory for Conservation and Utilization of Bioresources and Key Laboratory for Microbial Resources of the Ministry of Education, Yunnan University, Kunming 650091, P. R. China, (phone: +86-871-5032538). (2)Laboratory for Conservation and Utilization of Bioresources and Key Laboratory for Microbial Resources of the Ministry of Education, Yunnan University, Kunming 650091, P. R. China, (phone: +86-871-5032538). . (3)Laboratory for Conservation and Utilization of Bioresources and Key Laboratory for Microbial Resources of the Ministry of Education, Yunnan University, Kunming 650091, P. R. China, (phone: +86-871-5032538). .
The five studied bacterial strains could produce volatile organic compounds (VOCs) that kill nematodes. Based on their 16S rRNA sequences, these strains were identified as Pseudochrobactrum saccharolyticum, Wautersiella falsenii, Proteus hauseri, Arthrobacter nicotianae, and Achromobacter xylosoxidans. The bacterial VOCs were extracted using solid-phase micro-extraction (SPME) and subsequently identified by GC/MS analysis. The VOCs covered a wide range of aldehydes, ketones, alkyls, alcohols, alkenes, esters, alkynes, acids, ethers, as well as heterocyclic and phenolic compounds. Among the 53 VOCs identified, 19 candidates, produced by different bacteria, were selected to test their nematicidal activity (NA) against Caenorhabditis elegans and Meloidogyne incognita. The seven compounds with the highest NAs were acetophenone, S-methyl thiobutyrate, dimethyl disulfide, ethyl 3,3-dimethylacrylate, nonan-2-one, 1-methoxy-4-methylbenzene, and butyl isovalerate. Among them, S-methyl thiobutyrate showed a stronger NA than the commercial insecticide dimethyl disulfide. It was reported for the first time here that the five bacterial strains as well as S-methyl thiobutyrate, ethyl 3,3-dimethylacrylate, 1-methoxy-4-methylbenzene, and butyl isovalerate possess NA. These strains and compounds might provide new insights in the search for novel nematicides.
DOI: 10.1002/cbdv.201400342 PMID: 26363885 [Indexed for MEDLINE]

[3]. Sci Total Environ. 2020 May 15;717:137175. doi: 10.1016/j.scitotenv.2020.137175. Epub 2020 Feb 8.
Malodorous gases production from food wastes decomposition by indigenous microorganisms.
Zhang Y(1), Liang Z(1), Tang C(1), Liao W(1), Yu Y(1), Li G(2), Yang Y(3), An T(1).
Author information: (1)Guangdong Key Laboratory of Environmental Catalysis and Health Risk Control, Guangzhou Key Laboratory Environmental Catalysis and Pollution Control, School of Environmental Science and Engineering, Institute of Environmental Health and Pollution Control, Guangdong University of Technology, Guangzhou 510006, China. (2)Guangdong Key Laboratory of Environmental Catalysis and Health Risk Control, Guangzhou Key Laboratory Environmental Catalysis and Pollution Control, School of Environmental Science and Engineering, Institute of Environmental Health and Pollution Control, Guangdong University of Technology, Guangzhou 510006, China; Synergy Innovation Institute of GDUT, Shantou 515100, China. Electronic address: . (3)Guangdong Key Laboratory of Environmental Catalysis and Health Risk Control, Guangzhou Key Laboratory Environmental Catalysis and Pollution Control, School of Environmental Science and Engineering, Institute of Environmental Health and Pollution Control, Guangdong University of Technology, Guangzhou 510006, China; Synergy Innovation Institute of GDUT, Shantou 515100, China.
Volatile organic compounds (VOCs) produced during the degradation of food wastes may harm to the health of people and create annoyance in adjacent communities. In this work, the VOCs emitted from the decomposition food wastes including fruit, meat and vegetable, and their microbial communities were measured in three individual 57-L reactors for 61 days. Total of 232.8, 373.5, and 191.1 μg·kg-1·h-1 VOCs with oxygenated VOCs (57.6%), volatile organic sulfur compounds (VOSCs, 58.6%) and VOSCs (54.9%) as the main group were detected during fruit, meat and vegetable fermentation, respectively. 2-Butanone (55.1%) and ethyl acetate (13.8%) were the two most abundant VOCs from fruit wastes, while dimethyl sulfide (68.0 and 26.6%) and dimethyl disulfide (89.2 and 10.1%) were in vegetable and meat wastes. The predominant Firmicutes represented 93.0-99.9% of the bacterial communities of meat decomposition, while Firmicutes and Proteobacteria were the dominant phyla throughout the fruit digestion process. Proteobacteria (16.9%-83.6%) was the dominant phylum in vegetable wastes, followed by Bacteroidetes, Firmicutes, and Actinobacteria. Malodorous VOCs emissions were highly affected by microbial activity, the abundant Weissella, Leuconostoc and Enterobacteriaceae in vegetable wastes showed correlation with carbon disulfide and dimethyl sulfide, while dominant Peptococcus, Bacteroides, Lactobacillales and Peptoniphilus in meat wastes was related to dimethyl disulfide. Overall, significant differences and correlation between VOCs emission profiles and bacterial communities among different food wastes decomposition were observed. These data contribute to a more comprehensive understanding the relationship between microbial community dynamics and malodorous VOCs emission.
DOI: 10.1016/j.scitotenv.2020.137175 PMID: 32062272 [Indexed for MEDLINE]

[4]. Molecules. 2019 Sep 18;24(18):3392. doi: 10.3390/molecules24183392.
Effect of Ethanol on the Adsorption of Volatile Sulfur Compounds on Solid Phase Micro-Extraction Fiber Coatings and the Implication for Analysis in Wine.
Davis PM(1), Qian MC(2)(3).
Author information: (1)Department of Food Science & Technology, Oregon State University, Corvallis, OR 97331, USA. . (2)Department of Food Science & Technology, Oregon State University, Corvallis, OR 97331, USA. . (3)Oregon Wine Research Institute, Oregon State University, Corvallis, OR 97331, USA. .
Complications in the analysis of volatile sulfur compounds (VSC) in wine using solid-phase microextraction (SPME) arise from sample variability. Constituents of the wine matrix, including ethanol, affect the volatility and adsorption of sulfur volatiles on SPME fiber coatings (Carboxen- polydimethylsiloxane(PDMS); DVB-Carboxen-PDMS and DVB-PDMS), which can impact sensitivity and accuracy. Here, several common wine sulfur volatiles, including hydrogen sulfide (H2S), methanethiol (MeSH), dimethyl sulfide (DMS), dimethyl disulfide (DMDS), dimethyl trisulfide (DMTS), diethyl disulfide (DEDS), methyl thioacetate (MeSOAc), and ethyl thioacetate (EtSOAc) are analyzed, using SPME followed by gas chromatography (GC), using a system equipped with a pulsed-flame photometric detection (PFPD) system, at various ethanol concentrations in a synthetic wine matrix. Ethyl methyl sulfide (EMS), diethyl sulfide (DES), methyl isopropyl sulfide (MIS), ethyl isopropyl sulfide (EIS), and diisopropyl disulfide (DIDS) are evaluated as internal standards. The absorption of volatile compounds on the SPME fiber is greatly affected by ethanol. All compounds exhibit a stark decrease in detectability with the addition of ethanol, especially between 0.0 and 0.5% v/v. However, the ratio of interested sulfur compounds to the internal standard becomes more stable when the total alcohol concentration exceeds 2%. EMS was found to best resemble DMS. EIS and DES were found to best resemble DMDS, MeSOAc, and EtSOAc. DIDS was found to best resemble DEDS, DMTS, H2S, and MeSH.
DOI: 10.3390/molecules24183392 PMCID: PMC6767315 PMID: 31540469 [Indexed for MEDLINE]

[5]. Water Res. 2016 Jan 1;88:308-321. doi: 10.1016/j.watres.2015.10.020. Epub 2015 Oct 20.
Prioritisation of odorants emitted from sewers using odour activity values.
Sivret EC(1), Wang B(2), Parcsi G(3), Stuetz RM(4).
Author information: (1)UNSW Water Research Centre, School of Civil and Environmental Engineering, The University of New South Wales, Sydney, NSW, 2052, Australia. Electronic address: . (2)UNSW Water Research Centre, School of Civil and Environmental Engineering, The University of New South Wales, Sydney, NSW, 2052, Australia. Electronic address: . (3)UNSW Water Research Centre, School of Civil and Environmental Engineering, The University of New South Wales, Sydney, NSW, 2052, Australia. Electronic address: . (4)UNSW Water Research Centre, School of Civil and Environmental Engineering, The University of New South Wales, Sydney, NSW, 2052, Australia. Electronic address: .
Volatile sulfur and volatile organic compound (VSC and VOC, respectively) emissions were measured over a 3.5 year period from 21 field monitoring sites across Australia to determine their potential contribution to sewer odours and support the evaluation of odour abatement processes used to treat sewer emissions. Measured VOC concentrations were generally less than 250 μg/m(3), although some VOCs (toluene, trimethylbenzene and cymene) were present at higher concentrations. In general, sewer headspace VOCs are unlikely to be a significant contributor to sewer odours and VOC monitoring is only recommended for sites with a history of significant trade waste discharges or where odour character descriptors are typical of VOCs. A range of VSCs were identified, including hydrogen sulfide, ethyl mercaptan, methyl mercaptan, dimethyl sulfide, dimethyl disulfide, dimethyl trisulfide, carbon disulfide, and carbonyl sulfide. From a concentration perspective, the VSCs were dominated by hydrogen sulfide, followed by methyl mercaptan, and then a range of sulfides. Significant variations in VSC concentration and relative importance were observed between the cities and all identified VSCs were potentially odorous. An odorant prioritisation methodology to identify key and high priority odorants was developed and successfully demonstrated. While some high priority VOCs were identified, VSCs (hydrogen sulfide, methyl mercaptan, dimethyl sulfide, and dimethyl disulfide) were the dominant priority odorants. A wider range of VSCs should be assessed in addition to hydrogen sulfide to improve the evaluation of odour abatement processes.
DOI: 10.1016/j.watres.2015.10.020 PMID: 26512809 [Indexed for MEDLINE]