2-Mercaptoethanol
Names | |
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Preferred IUPAC name
2-Sulfanylethan-1-ol[1] | |
Other names
2-Mercaptoethan-1-ol
2-Hydroxy-1-ethanethiol β-Mercaptoethanol Thioglycol Beta-merc | |
Identifiers | |
3D model (
JSmol ) |
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3DMet | |
773648 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.000.422 |
EC Number |
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1368 | |
KEGG | |
MeSH | Mercaptoethanol |
PubChem CID
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RTECS number
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UNII | |
UN number | 2966 |
CompTox Dashboard (EPA)
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Properties | |
C2H6OS | |
Molar mass | 78.13 g·mol−1 |
Odor | Disagreeable, distinctive |
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 | 0.76 hPa (at 20 °C); 4.67 hPa (at 40 °C) |
Acidity (pKa) | 9.643 |
Basicity (pKb) | 4.354 |
Refractive index (nD)
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1.4996 |
Hazards | |
GHS labelling: | |
Danger | |
H301, H310, H315, H317, H318, H330, H410 | |
P260, P273, P280, P284, P301+P310, P302+P350 | |
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)[2] 150 mg/kg (skin, rabbit)[2] |
Related compounds | |
Related compounds
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1,2-Ethanedithiol
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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2-Mercaptoethanol (also β-mercaptoethanol, BME, 2BME, 2-ME or β-met) is the
Production
2-Mercaptoethanol is manufactured industrially by the reaction of ethylene oxide with hydrogen sulfide. Thiodiglycol and various zeolites catalyze the reaction.[3]
Reactions
2-Mercaptoethanol reacts with
Applications
Reducing proteins
Some proteins can be denatured by 2-mercaptoethanol, which cleaves the
residues. In the case of excess 2-mercaptoethanol, the following equilibrium is shifted to the right:- RS–SR + 2 HOCH2CH2SH ⇌ 2 RSH + HOCH2CH2S–SCH2CH2OH
By breaking the S-S bonds, both the
2-Mercaptoethanol is often used interchangeably with dithiothreitol (DTT) or the odorless tris(2-carboxyethyl)phosphine (TCEP) in biological applications.
Although 2-mercaptoethanol has a higher volatility than DTT, it is more stable: 2-mercaptoethanol's half-life is more than 100 hours at pH 6.5 and 4 hours at pH 8.5; DTT's half-life is 40 hours at pH 6.5 and 1.5 hours at pH 8.5.[8][9]
Preventing protein oxidation
2-Mercaptoethanol and related reducing agents (e.g., DTT) are often included in enzymatic reactions to inhibit the oxidation of free sulfhydryl residues, and hence maintain protein activity. It is often used in enzyme assays as a standard buffer component.[10]
Denaturing ribonucleases
2-Mercaptoethanol is used in some RNA isolation procedures to eliminate
Deprotecting carbamates
Some
Safety
2-Mercaptoethanol is considered toxic, causing irritation to the nasal passageways and respiratory tract upon inhalation, irritation to the skin, vomiting and stomach pain through ingestion, and potentially death if severe exposure occurs.[13]
See also
- Dithiothreitol (DTT)
- Dithiobutylamine (DTBA)
- TCEP
References
- ISBN 978-0-85404-182-4.
The prefixes 'mercapto' (–SH), and 'hydroseleno' or selenyl (–SeH), etc. are no longer recommended.
- ^ a b 2-Mercaptoethanol
- ISBN 978-3527306732.
- ^ "1,3-Dithiolanes, 1,3-Dithianes". Organic Chemistry Portal. Archived from the original on 17 May 2008. Retrieved 27 May 2008.
- PMID 14719975.
- ^ "2-Mercaptoethanol". Chemicalland21.com. Archived from the original on 2006-10-05. Retrieved 8 October 2006.
- PMID 17921203.
- ISBN 978-0-9720774-4-6.
- .
- PMID 3921014.
- ISBN 0-7167-4339-6.
- S2CID 248776636.
- ^ "Material Safety Data Sheet". Merck. Retrieved 24 September 2023.