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Mercaptoethanol

2-Mercaptoethanol
Skeletal formula of 2-mercaptoethanol
Spacefill model of 2-mercaptoethanol
Names
Preferred IUPAC name
2-Sulfanylethan-1-ol
Other names
2-Mercaptoethan-1-ol (no longer recommended)
2-Hydroxy-1-ethanethiol
β-Mercaptoethanol
Thioglycol
Identifiers
3D model (JSmol)
3DMet B00201
773648
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.000.422
EC Number 200-464-6
1368
KEGG
MeSH Mercaptoethanol
PubChem CID
RTECS number KL5600000
UN number 2966
Properties
C2H6OS
Molar mass 78.13 g·mol−1
Density 1.114 g/cm3
Melting point −100 °C (−148 °F; 173 K)
Boiling point 157 °C; 314 °F; 430 K
log P -0.23
Vapor pressure 100 Pa (at 20 °C)
Acidity (pKa) 9.643
Basicity (pKb) 4.354
1.4996
Hazards
Safety data sheet msds.chem.ox.ac.uk
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H301, H310, H315, H317, H318, H330, H410
P260, P273, P280, P284, P301+310, P302+350
Flash point 68 °C (154 °F; 341 K)
Explosive limits 18%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
244 mg/Kg (oral, rat)
150 mg/kg (skin, rabbit)
Related compounds
Related compounds
Ethylene glycol

1,2-Ethanedithiol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

1,2-Ethanedithiol

2-Mercaptoethanol (also β-mercaptoethanol, BME, 2BME, 2-ME or β-met) is the chemical compound with the formula HOCH2CH2SH. 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 odor, while unpleasant, is less objectionable than related thiols.

2-Mercaptoethanol may be prepared by the action of hydrogen sulfide on ethylene oxide:

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

Some proteins can be denatured by 2-mercaptoethanol, which cleaves the disulfide bonds that may form between thiol groups of cysteine residues. In the case of excess 2-mercaptoethanol, the following equilibrium is shifted to the right:

By breaking the S-S bonds, both the tertiary structure and the quaternary structure of some proteins can be disrupted. Because of its ability to disrupt the structure of proteins, it was used in the analysis of proteins, for instance, to ensure that a protein solution contains monomeric protein molecules, instead of disulfide linked dimers or higher order oligomers. However, since 2-mercaptoethanol forms adducts with free cysteines and is somewhat more toxic, dithiothreitol (DTT) is generally more used especially in SDS-PAGE. DTT is also a more powerful reducing agent with a redox potential (at pH 7) of −0.33 V, compared to −0.26 V for 2-mercaptoethanol.


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