Ethyl methanesulfonate

Ethyl methanesulfonate^[1]

Names
IUPAC name 1-Methylsulfonyloxyethane
Other names Ethyl mesylate Ethyl methanesulphonate
Identifiers
Abbreviations	EMS
CAS Registry Number	62-50-0 Y
ChEBI	CHEBI:23994 N
ChEMBL	ChEMBL338686 Y
ChemSpider	5887 Y
InChI InChI=1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3 Y Key: PLUBXMRUUVWRLT-UHFFFAOYSA-N Y InChI=1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3 Key: PLUBXMRUUVWRLT-UHFFFAOYAM
Jmol-3D images	Image
KEGG	C19239 N
PubChem	6113
SMILES O=S(=O)(OCC)C
Properties
Chemical formula	CH3SO3C2H5
Molar mass	124.16 g/mol
Appearance	Clear colorless liquid
Density	1.1452 g/cm3 (22 °C)
Melting point	< 25 °C
Boiling point	213 to 213.5 °C (415.4 to 416.3 °F; 486.1 to 486.6 K)
Hazards
NFPA 704	1 1 0
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Ethyl methanesulfonate (EMS) is a mutagenic, teratogenic, and possibly carcinogenic organic compound with formula CH₃SO₃C₂H₅. It produces random mutations in genetic material by nucleotide substitution; particularly by guanine alkylation. This typically produces only point mutations. It can induce mutations at a rate of 5x10⁻⁴ to 5x10⁻² per gene without substantial killing. The ethyl group of EMS reacts with guanine in DNA, forming the abnormal base O-6-ethylguanine. During DNA replication, DNA polymerases that catalyze the process frequently place thymine, instead of cytosine, opposite O-6-ethylguanine. Following subsequent rounds of replication, the original G:C base pair can become an A:T pair (a transition mutation). This changes the genetic information, is often harmful to cells, and can result in disease.

EMS is often used in genetics as a mutagen. Mutations induced by EMS can then be studied in genetic screens or other assays.

See also

• Mutagenesis (molecular biology technique)

References