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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
Hazards
MSDS	Oxford MSDS
EU classification	Toxic (T)
R-phrases	R23 R24 R25 R37 R38 R41
S-phrases	S26 S36 S37 S39 S45 S53
Related compounds
Related compounds	ethylene glycol 1,2-ethanedithiol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

2-Mercaptoethanol (also β-mercaptoethanol, or "2BME") is the chemical compound with the formula HOCH₂CH₂SH. It is a hybrid of ethylene glycol, HOCH₂CH₂OH, and 1,2-ethanedithiol, HSCH₂CH₂SH. ME or βME, as it is commonly abbreviated, is used to reduce disulfide bonds and can act as a biological antioxidant by scavenging hydroxyl radicals (amongst others) . It is widely used because the hydroxyl group confers solubility in water and lowers the volatility. Due to its diminished vapor pressure, its odour, while unpleasant, is less objectionable than related thiols.

Preparation

ME may be prepared by the action of hydrogen sulfide on ethylene oxide:¹

Applications

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

cysS-Scys + 2 HOCH₂CH₂SH → 2 cysSH + HOCH₂CH₂S-SCH₂CH₂OH

By breaking the S-S bonds, both the tertiary structure and the quaternary structure of the protein can be disrupted.² Because of its ability to disrupt the structure of proteins, it is used in the analysis of proteins.

2-Mercaptoethanol is often used interchangeably with dithiothreitol (DTT) or the odorless tris(2-carboxyethyl)phosphine (TCEP) in biological applications.

Reactions

2-Mercaptoethanol reacts with aldehydes and ketones to give the corresponding oxathiolanes. This makes 2-mercaptoethanol useful as a protecting group.³

Biological effects

2-Mercaptoethanol is one of the few chemicals that extends the maximum as well as the median life span of mice.⁴ In microgram quantities, 2-mercaptoethanol has been observed to have a number of possibly beneficial effects on laboratory mice.⁵

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. ^ "2-Mercaptoethanol". Chemicalland21.com.
3. ^ "1,3-Dithiolanes, 1,3-Dithianes". Organic Chemistry Portal.
4. ^ M.L. Heidrick, L.C. Hendricks and D.E. Cook (1984). "Effect of dietary 2-mercaptoethanol on the life span, immune system, tumor incidence and lipid peroxidation damage in spleen lymphocytes of aging BC3F1 mice". Mech. Ageing Dev. 27 (3): 341-58. doi:10.1016/0047-6374(84)90057-5. PMID 6334792. 
5. ^ L. Pénzesa, R. C. Nobleb, E. Beregia, S. Imrec, J. Izsáka and O. Regius (1988). "Effect of 2-mercaptoethanol on some metabolic indices of ageing of CBA/Ca inbred mice". Mech. Ageing Dev. 45 (1): 75-92. doi:10.1016/0047-6374(88)90021-8. PMID 3216730. 

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