Dimethyl sulfide Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur Dimethyl sulfide compound with the formula (CH3)2S. Dimethyl sulfide is a flammable liquid that boils at 37 °C (99 °F) and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably maize, cabbage, beetroot, and seafoods. It is also an indication of bacterial contamination in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate (DMSP), and is also produced by the bacterial metabolism of methanethiol. Names Preferred IUPAC name (Methylsulfanyl)methane[1] Contents Other names [1] Natural occurrence (Methylthio)methane Physiology of dimethyl sulfide Dimethyl sulfide[1] Smell Identifiers Preparation CAS Number 75-18-3 (http://ww w.commonchemistr Industrial uses y.org/ChemicalDeta Other uses il.aspx?ref=75-18- Safety 3) See also 3D model Interactive image (h (JSmol) References ttps://chemapps.sto External links laf.edu/jmol/jmol.ph p?model=CSC) 3DMet B00138 (http://ww Natural occurrence w.3dmet.dna.affrc.g o.jp/cgi/show_data. DMS originates primarily from DMSP, a major secondary metabolite php?acc=B00138) in some marine algae.[2] DMS is the most abundant biological sulfur compound emitted to the atmosphere.[3][4] Emission occurs over the Beilstein 1696847 oceans by phytoplankton. DMS is also produced naturally by Reference bacterial transformation of dimethyl sulfoxide (DMSO) waste that is ChEBI CHEBI:17437 (http disposed of into sewers, where it can cause environmental odor s://www.ebi.ac.uk/c [5] problems. hebi/searchId.do?c hebiId=17437) DMS is oxidized in the marine atmosphere to various sulfur- containing compounds, such as sulfur dioxide, dimethyl sulfoxide ChEMBL ChEMBL15580 (htt [6] (DMSO), dimethyl sulfone, methanesulfonic acid and sulfuric acid. ps://www.ebi.ac.uk/ Among these compounds, sulfuric acid has the potential to create new chembldb/index.ph aerosols which act as cloud condensation nuclei. Through this p/compound/inspec interaction with cloud formation, the massive production of t/ChEMBL15580) atmospheric DMS over the oceans may have a significant impact on ChemSpider 1039 (http://www.ch the Earth's climate.[7][8] The CLAW hypothesis suggests that in this emspider.com/Che [9] manner DMS may play a role in planetary homeostasis. mical-Structure.103 9.html) Marine phytoplankton also produce dimethyl sulfide,[10] and DMS is also produced by bacterial cleavage of extracellular DMSP.[11] DMS ECHA 100.000.770 (http has been characterized as the "smell of the sea",[12] though it would InfoCard s://echa.europa.eu/ be more accurate to say that DMS is a component of the smell of the substance-informati sea, others being chemical derivatives of DMS, such as oxides, and on/-/substanceinfo/ yet others being algal pheromones such as dictyopterenes.[13] 100.000.770) Dimethyl sulfide also is an odorant emitted by kraft pulping mills, and EC Number 200-846-2 it is a byproduct of Swern oxidation. KEGG C00580 (https://ww w.kegg.jp/entry/C00 Dimethyl sulfide, dimethyl disulfide, and dimethyl trisulfide have been found among the volatiles given off by the fly-attracting plant 580) known as dead-horse arum (Helicodiceros muscivorus). Those MeSH dimethyl+sulfide (ht compounds are components of an odor like rotting meat, which tps://www.nlm.nih.g attracts various pollinators that feed on carrion, such as many species ov/cgi/mesh/2014/ [14] of flies. MB_cgi?mode=&ter m=dimethyl+sulfid Physiology of dimethyl sulfide e) PubChem CID 1068 (https://pubch Dimethyl sulfide is normally present at very low levels in healthy em.ncbi.nlm.nih.go people, namely <7nM in blood, <3 nM in urine and 0.13 – 0.65 nM v/compound/1068) on expired breath.[15][16] RTECS PV5075000 At pathologically dangerous concentrations, this is known as number dimethylsulfidemia. This condition is associated with blood borne UNII halitosis and dimethylsulfiduria.[17][18][19] QS3J7O7L3U (http s://fdasis.nlm.nih.go In people with chronic liver disease (cirrhosis), high levels of dimethyl v/srs/srsdirect.jsp?r sulfide may be present the breath, leading to an unpleasant smell (fetor egno=QS3J7O7L3 hepaticus). U) UN number 1164 Smell CompTox DTXSID9026398 (h Dashboard ttps://comptox.epa. Dimethyl sulfide has a characteristic smell commonly described as (EPA) cabbage-like. It becomes highly disagreeable at even quite low gov/dashboard/DT concentrations. Some reports claim that DMS has a low olfactory XSID9026398) threshold that varies from 0.02 to 0.1 ppm between different persons, InChI but it has been suggested that the odor attributed to dimethyl sulfide InChI=1S/C2H6S/c1-3-2/h1-2H3 may in fact be due to di- and polysulfides and thiol impurities, since Key: QMMFVYPAHWMCMS-UHFFFAOYSA- the odor of dimethyl sulfide is much less disagreeable after it is freshly N [20] washed with saturated aqueous mercuric chloride. Dimethyl Key: QMMFVYPAHWMCMS-UHFFFAOYAH sulfide is also available as a food additive to impart a savory flavor; in SMILES such use, its concentration is low. Beetroot,[21] asparagus,[22] cabbage, corn and seafoods produce dimethyl sulfide when cooked. CSC Properties Chemical C2H6S formula Dimethyl sulfide is also produced by marine planktonic micro- Molar mass 62.13 g·mol−1 organisms such as the coccolithophores and so is one of the main Appearance Colourless liquid components responsible for the characteristic odor of sea water aerosols, which make up a part of sea air. In the Victorian era, before Odor Cabbage, sulfurous DMS was discovered, the origin of sea air's 'bracing' aroma was Density 0.846 g cm−3 attributed to ozone.[23] Melting point −98 °C; −145 °F; 175 K Preparation Boiling point 35 to 41 °C; 95 to 106 °F; 308 to In industry dimethyl sulfide is produced by treating hydrogen sulfide 314 K with excess methanol over an aluminium oxide catalyst.[24] log P 0.977 Industrial uses Vapor 53.7 kPa (at 20 °C) pressure −6 3 Dimethyl sulfide has been used in petroleum refining to pre-sulfide Magnetic −44.9⋅10 cm /mol hydrodesulfurization catalysts, although other disulfides or susceptibility polysulfides are preferred and easier to handle. It is used as a (χ) presulfiding agent to control the formation of coke and carbon Refractive 1.435 monoxide in ethylene production. DMS is also used in a range of index (nD) organic syntheses, including as a reducing agent in ozonolysis Thermochemistry reactions. It also has a use as a food flavoring component. It can also Std enthalpy −66.9– be oxidized to dimethyl sulfoxide, (DMSO), which is an important of 63.9 kJ mol−1 industrial solvent. formation ⋅ ⦵ (ΔfH 298) The largest single commercial producer of DMS in the world is Gaylord Chemical Corporation. The Chevron Phillips Chemical Std enthalpy −2.1818– of 2.1812 MJ mol−1 company is also a major manufacturer of DMS. CP Chem produces combustion ⋅ this material at their facilities in Borger, Texas, USA and Tessenderlo, (Δ H⦵ ) Belgium. c 298 Hazards Other uses Safety data osha.gov (http://ww sheet w.osha.gov/dts/che Dimethyl sulfide is a Lewis base, classified as a soft ligand (see also micalsampling/data/ ECW model). Dimethyl sulfide finds a niche use as a displaceable CH_236505.html) ligand in chloro(dimethyl sulfide)gold(I) and other coordination GHS compounds. Dimethyl sulfide is also used in the ozonolysis of pictograms alkenes, reducing the intermediate trioxolane and oxidizing to DMSO, an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. GHS Signal Danger The process: alkene + ozone + DMS → aldehyde(1) + aldehyde(2) + word DMSO GHS hazard H225, H315, H318, statements H335 Safety GHS P210, P261, P280, precautionary P305+351+338 Dimethyl sulfide is highly flammable and an eye and skin irritant. It is statements harmful if swallowed. It has an unpleasant odor at even extremely low Flash point −36 °C (−33 °F; concentrations. Its ignition temperature is 205 °C. 237 K) See also Autoignition 206 °C (403 °F; temperature 479 K) Coccolithophore, a marine unicellular planktonic Explosive 19.7% photosynthetic algae, producer of DMS limits Dimethylsulfoniopropionate, a parent molecule of DMS Related compounds and methanethiol in the oceans Dimethyl selenide, a selenium analogue of DMS produced Related Dimethyl ether by bacteria and phytoplankton chalcogenides (dimethyl oxide) Dimethyl telluride, a tellurium analogue of DMS Dimethyl selenide Emiliania huxleyi, a coccolithophorid producing DMS Dimethyl telluride Swern oxidation Related Dimethyl ether Gaia hypothesis compounds Dimethyl sulfoxide Geosmin, the substance responsible for the odour of earth Dimethyl sulfone Petrichor, the earthy scent produced when rain falls on dry Except where otherwise noted, data soil are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). References verify (what is ?) 1. "CHAPTER P-6. Applications to Specific Classes of Infobox references Compounds". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 706. doi:10.1039/9781849733069-00648 (https://doi.org/ 10.1039%2F9781849733069-00648). ISBN 978-0-85404- 182-4. 2. Stefels, J.; Steinke, M.; Turner, S.; Malin, S.; Belviso, A. (2007). "Environmental constraints on the production and removal of the climatically active gas dimethylsulphide (DMS) and implications for ecosystem modelling" (https://d oi.org/10.1007/s10533-007-9091-5). Biogeochemistry. 83 (1–3): 245–275. doi:10.1007/s10533-007-9091-5 (https://do i.org/10.1007%2Fs10533-007-9091-5). 3. Kappler, Ulrike; Schäfer, Hendrik (2014). "Chapter 11. Transformations of Dimethylsulfide". In Peter M.H. Kroneck and Martha E. Sosa Torres (ed.). The Metal-Driven Biogeochemistry of Gaseous Compounds in the Environment. Metal Ions in Life Sciences. 14. Springer. pp. 279–313. doi:10.1007/978-94-017-9269-1_11 (https://d oi.org/10.1007%2F978-94-017-9269-1_11).