| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 08:17:38 -0600 |
| Update Date |
2013-05-17 15:58:10 -0600 |
| HMDB ID |
HMDB02151 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Dimethyl sulfoxide |
| 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. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (methylsulfinyl)methane
- Dimethyl sulfoxide
- Dimethyl sulfoxixde
- Dimethyl sulfur oxide
- Dimethyl sulphoxide
- Dimethyl sulpoxide
- DMSO
|
| Chemical Formula |
C2H6OS |
| Average Molecular Weight |
78.133 |
| Monoisotopic Molecular Weight |
78.013935504 |
| IUPAC Name |
methanesulfinylmethane |
| Traditional IUPAC Name |
dimethyl sulfoxide |
| CAS Registry Number |
67-68-5 |
| SMILES |
CS(C)=O |
| InChI Identifier |
InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 |
| InChI Key |
IAZDPXIOMUYVGZ-UHFFFAOYSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aliphatic Acyclic Compounds |
| Class |
Sulfoxides |
| Sub Class |
N/A |
| Other Descriptors |
- a small molecule(Cyc)
- sulfoxide(ChEBI)
|
| Substituents |
|
| Direct Parent |
Sulfoxides |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Osmolyte, enzyme cofactor, signalling
|
| Application |
Not Available
|
| Cellular locations |
Not Available
|
| Physical Properties |
|---|
| State |
Liquid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
18.5 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
1000 mg/mL |
Not Available |
| LogP |
-1.35 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
Not Available
|
| Biofluid Locations |
- Cerebrospinal Fluid (CSF)
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0 - 1.0 uM |
Adult (>18 years old) |
Both |
Normal
|
|
|
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
DB01093  |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB000764 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
659 |
| KEGG Compound ID |
C11143 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Dimethyl sulfoxide |
| NuGOwiki Link |
HMDB02151 |
| Metagene Link |
HMDB02151 |
| METLIN ID |
3985 |
| PubChem Compound |
679 |
| PDB ID |
DMS |
| ChEBI ID |
28262 |
| References |
|---|
| Synthesis Reference |
Goeb, Andre. Dimethyl sulfoxide. Ger. Offen. (1976), 12 pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Engelke UF, Tangerman A, Willemsen MA, Moskau D, Loss S, Mudd SH, Wevers RA: Dimethyl sulfone in human cerebrospinal fluid and blood plasma confirmed by one-dimensional (1)H and two-dimensional (1)H-(13)C NMR. NMR Biomed. 2005 Aug;18(5):331-6.
Pubmed: 15996001
|
