Ethyl methanesulfonate

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Ethyl methanesulfonate[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1-Methylsulfonyloxyethane
Other names
Ethyl mesylate
Ethyl methanesulphonate
Identifiers
3D model (JSmol)
Abbreviations EMS
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.488 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3 checkY
    Key: PLUBXMRUUVWRLT-UHFFFAOYSA-N checkY
  • InChI=1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
    Key: PLUBXMRUUVWRLT-UHFFFAOYAM
  • O=S(=O)(OCC)C
Properties
CH3SO3C2H5
Molar mass 124.16 g/mol
Appearance Clear colorless liquid
Density 1.1452 g/cm3 (22 °C)
Melting point < 25 °C
Boiling point 85–86 °C (185–187 °F; 358–359 K) /10 mmHg(lit)
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 [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Ethyl methanesulfonate (EMS) is a mutagenic, teratogenic, and possibly carcinogenic organic compound with formula C3H8SO3. 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 O6-ethylguanine. During DNA replication, DNA polymerases that catalyze the process frequently place thymine, instead of cytosine, opposite O6-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

References

  1. ^ Merck Index, 11th Edition, 3782.
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