2-Mercaptoethanol



2-Mercaptoethanol
IUPAC name 2-Hydroxy-1-ethanethiol
Other names 2-Mercaptoethanol
Thioglycol
β-Mercaptoethanol
Identifiers
CAS number 60-24-2
SMILES SCCO
Properties
Molecular formula C2H6OS
Molar mass 78.13 g mol−1
Density 1.11 g cm−3
Melting point

−100 °C

Boiling point

157-158 °C

Refractive index (nD) 1.4996
Related Compounds
Related compounds 1,2-ethanedithiol
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

2-Mercaptoethanol (also β-mercaptoethanol) is the thiols.

ME is prepared by the action of ethylene oxide:[1]

Biochemical properties

Proteins are denatured by 2-mercaptoethanol via its ability to cleave disulfide bonds:

cysSH + HOCH2CH2S-SCH2CH2OH

By breaking the S-S bonds, the quaternary structure of the protein is disrupted.[2] Because of its ability to disrupt the quaternary structure of proteins, it is used in the analysis of proteins.

2-Mercaptoethanol is often used interchangeably with TCEP) in biological applications.

Biomedical consequences

2-Mercaptoethanol is one of the few chemicals that extends the maximum as well as the median life span of mice.[3] In microgram quantities, 2-mercaptoethanol has been observed to have a number of possibly beneficial effects on laboratory mice.[4]

Organic chemistry

ME reacts with ketones to give the corresponding oxathiolanes:

References

  1. ^ Knight, J. J. "2-Mercaptoethanol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
  2. ^ Chemicalland: 2-mercaptoethanol
  3. ^ Yu, B.P.; Kang, C.M., Han, J.S., Kim, D.S. "Can antioxidant supplementation slow the aging process?" Biofactors 1998, Volume 7: pages93-101. "Can antioxidant supplementation slow the aging process?
  4. ^ Effect of 2-mercaptoethanol on some metabolic indices of ageing of CBA/Ca inbred mice
 
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