ChemFOnt: Showing chemical card for Dimethyl sulfoxide (CFc000001445)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:04 UTC

Chemfont ID

CFc000001445

Molecule Identification

Common Name

Dimethyl sulfoxide

Definition

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(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

Chemical Formula

C₂H₆OS

Average Molecular Weight

78.133

Monoisotopic Molecular Weight

78.013935504

IUPAC Name

methanesulfinylmethane

Traditional 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

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).

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Sulfoxides

Sub Class

Not Available

Direct Parent

Sulfoxides

Alternative Parents

Substituents

Sulfoxide
Sulfinyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfoxide (CHEBI:28262 )
a small molecule (DMSO )

Functional Ontology

Bitter

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Cerebrospinal Fluid (CSF) (PMID: 15996001)
Cerebrospinal fluid (HMDB: HMDB0002151)

Excreta

Biofluid or Excreta

Feces (PMID: 17314143)

Cellular substructure

Cytoplasm (HMDB: HMDB0002151)
Extracellular (HMDB: HMDB0002151)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0002151)

Enteral

Ingestion (HMDB: HMDB0002151)

Source

Exogenous

Exogenous (HMDB: HMDB0002151)

Food

Food (HMDB: HMDB0002151)

Vegetable

Cabbage

Cauliflower (FooDB: FOOD00031)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)
Spearmint (FooDB: FOOD00112)

Pulse

Bean

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0002151)
Fabaceae (HMDB: HMDB0002151)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Dimethyl Sulfoxide Electron Transfer (PathBank: SMP0122103)

Role

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	65.7 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-1.4	ChemAxon
logS	-0.08	ALOGPS
pKa (Strongest Basic)	-8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	20.73 m³·mol⁻¹	ChemAxon
Polarizability	7.91 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon