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Ethyl methanesulfonate

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Ethyl methanesulfonate
Skeletal formula
Ball-and-stick model
Names
IUPAC name 1-Methylsulfonyloxyethane
Other names Ethyl mesylate
Ethyl methanesulphonate
Identifiers
CAS Number
3D model (JSmol)
Abbreviations EMS
ChEMBL
ChemSpider
ECHA InfoCard 100.000.488 Edit this at Wikidata
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3Key: PLUBXMRUUVWRLT-UHFFFAOYSA-N
  • InChI=1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3Key: PLUBXMRUUVWRLT-UHFFFAOYAM
SMILES
  • O=S(=O)(OCC)C
Properties
Chemical formula CH3SO3C2H5
Molar mass 124.16 g/mol
Appearance Clear colorless liquid
Density 1.1452 g/cm (22 °C)
Melting point < 25 °C
Boiling point 213–213.5 °C, 486.2-486.7 K
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 to 5x10 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. 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.

References

  1. Merck Index, 11th Edition, 3782.
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