Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 14:17:38 UTC |
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Update Date | 2023-02-21 17:16:13 UTC |
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HMDB ID | HMDB0002151 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dimethyl sulfoxide |
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Description | Dimethyl sulfoxide (DMSO) is a key dipolar aprotic solvent. It is less toxic than other members of this class: dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, HMPA. Dimethyl sulfoxide is the chemical compound (CH3)2SO. This colorless liquid is an important "dipolar aprotic solvent." It is readily miscible in a wide range of organic solvents as well as water. It has a distinctive property of penetrating the skin very readily, allowing the handler to taste it. Some describe it as an "oyster-like" taste, others claim it tastes like garlic. DMSO is also employed as a rinsing agent in the electronics industry and, in its deuterated form (DMSO-d6), is a useful solvent in NMR due to its ability to dissolve a wide range of chemical compounds and its minimal interference with the sample signals. In cryobiology DMSO has been used as a cryoprotectant and is still an important constituent of cryoprotectant vitrification mixtures used to preserve organs, tissues, and cell suspensions. It is particularly important in the freezing and long-term storage of embryonic stem cells and hematopoietic stem cell, which are often frozen in a mixture of 10% DMSO and 90% fetal calf serum. As part of an autologous bone marrow transplant the DMSO is re-infused along with the patient's own hematopoietic stem cell. Dimethyl sulfoxide is a by-product of wood pulping. One of the leading suppliers of DMSO is the Gaylord company in the USA. DMSO is frequently used as solvent in a number of chemical reactions. In particular it is an excellent reaction solvent for SN2 alkylations: it is possible to alkylate indoles with very high yields using potassium hydroxide as the base and a similar reaction also occurs with phenols. DMSO can be reacted with methyl iodide to form a sulfoxonium ion which can be reacted with sodium hydride to form a sulfur ylide. The methyl groups of DMSO are somewhat acidic in character (pKa=35) due to the stabilization of the resultant anions by the sulfoxide group. |
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Structure | InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 |
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Synonyms | Value | Source |
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(CH3)2SO | ChEBI | Dimethyl sulfur oxide | ChEBI | Dimethyl sulphoxide | ChEBI | Dimethyli sulfoxidum | ChEBI | Dimethylsulfoxid | ChEBI | Dimethylsulfoxyde | ChEBI | Dimetil sulfoxido | ChEBI | DMSO | ChEBI | Methylsulfinylmethane | ChEBI | S(O)Me2 | ChEBI | Sulfinylbis(methane) | ChEBI | Rimso-50 | Kegg | Zymso | Kegg | Dimethyl sulphur oxide | Generator | Dimethyli sulphoxidum | Generator | Dimethylsulphoxid | Generator | Dimethylsulphoxyde | Generator | Dimetil sulphoxido | Generator | Methylsulphinylmethane | Generator | Sulphinylbis(methane) | Generator | (Methylsulfinyl)methane | HMDB | Dimethyl sulfoxixde | HMDB | Dimethyl sulpoxide | HMDB | Dimethylsulphoxide | MeSH, HMDB | Rheumabene | MeSH, HMDB | Rimso | MeSH, HMDB | Dimexide | MeSH, HMDB | Research ind. corp. brand 1 OF dimethyl sulfoxide | MeSH, HMDB | Shire brand OF dimethyl sulfoxide | MeSH, HMDB | Sulphoxide, dimethyl | MeSH, HMDB | Dimethylsulphinyl | MeSH, HMDB | Merckle brand OF dimethyl sulfoxide | MeSH, HMDB | Research ind. corp. brand 2 OF dimethyl sulfoxide | MeSH, HMDB | Sclerosol | MeSH, HMDB | Sulfoxide, dimethyl | MeSH, HMDB | Dimethylsulfoxide | MeSH, HMDB | rimso 100 | MeSH, HMDB | Rimso50 | MeSH, HMDB | Rimso 50 | MeSH, HMDB |
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Chemical Formula | C2H6OS |
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Average Molecular Weight | 78.133 |
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Monoisotopic Molecular Weight | 78.013935504 |
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IUPAC Name | methanesulfinylmethane |
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Traditional Name | dimethyl sulfoxide |
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CAS Registry Number | 67-68-5 |
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SMILES | CS(C)=O |
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InChI Identifier | InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 |
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InChI Key | IAZDPXIOMUYVGZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H). |
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Kingdom | Organic compounds |
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Super Class | Organosulfur compounds |
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Class | Sulfoxides |
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Sub Class | Not Available |
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Direct Parent | Sulfoxides |
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Alternative Parents | |
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Substituents | - Sulfoxide
- Sulfinyl compound
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 18.5 °C | Not Available | Boiling Point | 189.00 to 190.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 1000 mg/mL | Not Available | LogP | -1.35 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Dimethyl sulfoxide EI-B (Non-derivatized) | splash10-03fr-9000000000-f0f118841efd8b3297a3 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl sulfoxide EI-B (Non-derivatized) | splash10-03fs-9000000000-945240052686ea267e2b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl sulfoxide EI-B (Non-derivatized) | splash10-03fs-9000000000-378b716bc39417224511 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl sulfoxide EI-B (Non-derivatized) | splash10-03fr-9000000000-f0f118841efd8b3297a3 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl sulfoxide EI-B (Non-derivatized) | splash10-03fs-9000000000-945240052686ea267e2b | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Dimethyl sulfoxide EI-B (Non-derivatized) | splash10-03fs-9000000000-378b716bc39417224511 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dimethyl sulfoxide GC-MS (Non-derivatized) - 70eV, Positive | splash10-01t9-9000000000-a87469bb1afda1828bbe | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Dimethyl sulfoxide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-03fr-9000000000-1db858034b22d1646592 | 2014-09-20 | Not Available | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Dimethyl sulfoxide 30V, Positive-QTOF | splash10-0002-9000000000-b96781268f9bbbcb1544 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dimethyl sulfoxide 10V, Positive-QTOF | splash10-004i-9000000000-16f85b2cb3628d8d9358 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dimethyl sulfoxide 35V, Positive-QTOF | splash10-03dj-9000000000-c11b31839f52d556db57 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Dimethyl sulfoxide 0V, Positive-QTOF | splash10-004i-9000000000-6fd68fb341597894c9e9 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 10V, Positive-QTOF | splash10-004i-9000000000-c8f7a9f09c8bb456283c | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 20V, Positive-QTOF | splash10-004i-9000000000-d8d98568ae59afba65e6 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 40V, Positive-QTOF | splash10-03di-9000000000-e0a36c290f004f302f0b | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 10V, Negative-QTOF | splash10-004i-9000000000-89687ba96456a97fb486 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 20V, Negative-QTOF | splash10-01t9-9000000000-04ddc1322b21e4817d57 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 40V, Negative-QTOF | splash10-0a4i-9000000000-d90c2fed7aad139b406c | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 10V, Negative-QTOF | splash10-004i-9000000000-50c596e219854897fad2 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 20V, Negative-QTOF | splash10-004i-9000000000-50c596e219854897fad2 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 40V, Negative-QTOF | splash10-0bt9-9000000000-102e2e8c382c8f4c1975 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 10V, Positive-QTOF | splash10-004i-9000000000-28072bae45639cb50943 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 20V, Positive-QTOF | splash10-03di-9000000000-670c7176bed65aef23f5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Dimethyl sulfoxide 40V, Positive-QTOF | splash10-03di-9000000000-9ae0f01cd17306d4ecf0 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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