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2-mercaptoethanol
Sign in to saveAlso known as 2-Sulfhydryl-Ethanol, thioglycol, β-mercaptoethanol, 2-hydroxy-1-ethanethiol, mercaptoethanol, Beta-Mercaptoethanol
2-Mercaptoethanol is the organosulfur compound with the formula HOCH2CH2SH. ME or βME, as it is commonly abbreviated, is used to reduce disulfide bonds. 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.
Chemical data
- Formula
- C2H6OS
- Molecular weight
- 78.14 g/mol
- IUPAC name
- 2-sulfanylethanol
- SMILES
- C(CS)O
- InChIKey
- DGVVWUTYPXICAM-UHFFFAOYSA-N
- XLogP
- -0.2
- Polar surface area
- 21.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
12,431 papers- Review: 2-mercaptoethanol alteration of in vitro immune functions of species other than murine.Journal of immunological methods · 2014
- 2-Mercaptoethanol promotes porcine oocyte maturation in vitro by maintaining autophagy homeostasis.Theriogenology · 2022
- 2-Mercaptoethanol protects against DNA double-strand breaks after kidney ischemia and reperfusion injury through GPX4 upregulation.Pharmacological reports : PR · 2022
- Reducing offsite modifications using 2-mercaptoethanol for LC-MS analyses.Biochemical and biophysical research communications · 2025
- 2-Mercaptoethanol (2-ME)-based IATs or Polybrene method mitigates the interference of daratumumab on blood compatibility tests.Hematology (Amsterdam, Netherlands) · 2021
via PubMed
~4 min read
Encyclopedic overview
10 sectionsContents
- Production
- Reactions
- Applications
- Reducing proteins
- Denaturing ribonucleases
- Deprotecting carbamates
- Genetic transformation
- Safety
- See also
- References
2-Mercaptoethanol is the organosulfur compound with the formula HOCH2CH2SH. ME or βME, as it is commonly abbreviated, is used to reduce disulfide bonds. 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.
==Production== 2-Mercaptoethanol is manufactured industrially by the reaction of ethylene oxide with hydrogen sulfide. Thiodiglycol and various zeolites catalyze the reaction. 400px|upright=2.5|frameless|Reaction of ethylene oxide with hydrogen sulfide to form 2-mercaptoethanol in the presence of thiodiglycol as solvent and catalyst.
Excerpted from Wikipedia’s “2-mercaptoethanol” article, available under the CC BY-SA 4.0 licence.