2-Mercaptoethanol
You don't need to be Editor-In-Chief to add or edit content to WikiDoc. You can begin to add to or edit text on this WikiDoc page by clicking on the edit button at the top of this page. Next enter or edit the information that you would like to appear here. Once you are done editing, scroll down and click the Save page button at the bottom of the page.
| 2-Mercaptoethanol | |
|---|---|
| Image:2-Mercaptoethanol.svg | |
| Image:2-mercaptoethanol-3D-vdW.png | |
| IUPAC name | 2-Hydroxy-1-ethanethiol |
| Other names | 2-Mercaptoethanol Thioglycol β-Mercaptoethanol |
| Identifiers | |
| CAS number | |
| 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 | ethylene glycol 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 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 scavaging 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.
ME is prepared by the action of hydrogen sulfide on ethylene oxide:[1]
Biochemical properties
Proteins are denatured by 2-mercaptoethanol via its ability to cleave disulfide bonds:
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 dithiothreitol (DTT) or the odorless tris(2-carboxyethyl)phosphine (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 aldehydes and ketones to give the corresponding oxathiolanes:
References
- ↑ 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.
- ↑ Chemicalland: 2-mercaptoethanol
- ↑ 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?
- ↑ Effect of 2-mercaptoethanol on some metabolic indices of ageing of CBA/Ca inbred mice
External links
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
