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Information about Ethyl Methanesulfonate



Ethyl methanesulfonate[1]
IUPAC name1-Methylsulfonyloxyethane
Other namesEthyl mesylate
Ethyl methanesulphonate
Identifiers
AbbreviationsEMS
CAS number62-50-0
PubChem6113
SMILESCCOS(=O)(=O)C
InChIInChI=1/C3H8O3S/c1-3-6-7(2,4)5/h3H2,1-2H3
Properties
Molecular formulaC3H8O3S
Molar mass0 g mol-1
AppearanceClear colorless liquid
Density1.1452 at 22 °C
Melting point <25 °C
Boiling point 213-213.5 °C
Hazards
NFPA 704
1
1
0
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)


Ethyl methanesulfonate (EMS) is a mutagenic, teratogenic, and possibly carcinogenic organic compound with formula C3H8O3S. It produces random mutations in genetic material by nucleotide substitution; specifically 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. This changes the genetic information, is often harmful to cells, and can result in disease. Many mutagens cause a wide variety of cancers in humans.

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

Popular culture

In the 1982 movie Blade Runner, replicant Roy Batty asks Dr. Eldon Tyrell about the possibility of extending his preprogrammed lifespan by changing his genetic code with "EMS recombination". He is informed that ethyl methanesulfonate is a potent mutagen and that a test subject was "dead before he left the table."

References

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

External links

IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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PubChem is a database of chemical molecules. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH).
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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The IUPAC International Chemical Identifier (InChI) is a textual identifier for chemical substances, designed to provide a human-readable standard way to encode molecular information and to facilitate the search for such information in databases and on the web.
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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In physics, density is mass m per unit volume V—how heavy something is compared to its size. A small, heavy object, such as a rock or a lump of lead, is denser than a lighter object of the same size or a larger object of the same weight, such as pieces of
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. It defines the colloquial "fire diamond" used by emergency personnel to quickly and easily identify the risks posed by nearby hazardous materials.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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In biology, a mutagen (Latin, literally origin of change) is a physical or chemical agent that changes the genetic information (usually DNA) of an organism and thus increases the frequency of mutations above the natural background level.
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Teratology (from the Greek τέρᾰς (genitive τέρᾰτος), meaning monster, or marvel and
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The term carcinogen refers to any substance, radionuclide or radiation which is an agent directly involved in the promotion of cancer or in the facilitation
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organic compounds]] An organic compound is any member of a large class of chemical compounds whose molecules contain carbon; for historical reasons discussed below, a few types of compounds such as carbonates, carbon oxides and cyanides, as well as elemental carbon are
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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4, 2
(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1

Atomic radius 70 pm
Atomic radius (calc.
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1, −1
(amphoteric oxide)
Electronegativity 2.20 (Pauling scale) More

Atomic radius 25 pm
Atomic radius (calc.) 53 pm
Covalent radius 37 pm
Van der Waals radius 120 pm
Miscellaneous

Thermal conductivity (300 K) 180.
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2, −1
(neutral oxide)
Electronegativity 3.44 (Pauling scale)
Ionization energies
(more) 1st: 1313.9 kJmol−1
2nd: 3388.3 kJmol−1
3rd: 5300.5 kJmol−1

Atomic radius 60 pm
Atomic radius (calc.
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6
(strongly acidic oxide)
Electronegativity 2.58 (Pauling scale)
Ionization energies
(more) 1st: 999.6 kJmol−1
2nd: 2252 kJmol−1
3rd: 3357 kJmol−1

Atomic radius 100 pm
Atomic radius (calc.
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mutations are changes to the base pair sequence of the genetic material of an organism. Mutations can be caused by copying errors in the genetic material during cell division, by exposure to ultraviolet or ionizing radiation, chemical mutagens, or viruses, or can occur deliberately
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A nucleotide is a chemical compound that consists of 3 portions: a heterocyclic base, a sugar, and one or more phosphate groups. In the most common nucleotides the base is a derivative of purine or pyrimidine, and the sugar is the pentose (five-carbon sugar) deoxyribose or ribose.
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Guanine is one of the five main nucleobases found in the nucleic acids DNA and RNA; the others being adenine, cytosine, thymine, and uracil. With the formula C5H5N5
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Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion or a carbene (or their equivalents).
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Genetics is the science of heredity and variation in living organisms.[1][2] Knowledge of the inheritance of characteristics has been implicitly used since prehistoric times for improving crop plants and animals through selective breeding.
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genetic screen (often shortened to screen) is a procedure or test to identify and select individuals who possess a phenotype of interest. A genetic screen for new genes is often referred to as forward genetics as opposed to reverse genetics
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19th century - 20th century - 21st century
1950s  1960s  1970s  - 1980s -  1990s  2000s  2010s
1979 1980 1981 - 1982 - 1983 1984 1985

Year 1982 (MCMLXXXII
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Lifespan refers to the typical length of time that any particular organism can be expected to live. It may also refer to:
  • Life expectancy, the average lifespan expected of a group
  • Maximum life span, the maximum lifespan observed in a group

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