2-Mercaptoethanol

changed changed 477213767 2-Mercaptoethanol 2-mercaptoethanol 200.svg skin-invert-image 170px correct ?? Structural formula of 2-mercaptoethanol 2-mercaptoethanol-3D-balls.png bg-transparent correct ?? Ball and stick model of 2-mercaptoethanol 2-Sulfanylethan-1-ol Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 697 10.1039/9781849733069-FP001 978-0-85404-182-4 The prefixes ‘mercapto’ (–SH), and ‘hydroseleno’ or selenyl (–SeH), etc. are no longer recommended. 2-Mercaptoethan-1-ol2-Hydroxy-1-ethanethiolβ-MercaptoethanolThioglycolBeta-merc, BME, 2BME, 2-ME, β-met 60-24-2 correct CAS correct FDA 14R9K67URN 1567 1512 correct chemspider 200-464-6 2966 DB03345 correct drugbank C00928 changed kegg Mercaptoethanol 41218 correct EBI 254951 correct EBI KL5600000 773648 1368 B00201 OCCS 1S/C2H6OS/c3-1-2-4/h3-4H,1-2H2 correct chemspider DGVVWUTYPXICAM-UHFFFAOYSA-N correct chemspider 2 6 1 1 Colorless liquidSMARTCHEM 2-Mercaptoethanol https://smart-chem.ru/en/product-2-mercaptoethanol smart-chem.ru 30 April 2026 1.114 g/cm3 Disagreeable, distinctive −100 430 −0.23 0.76 hPa (at 20 °C);4.67 hPa (at 40 °C) 9.643 4.354 1.4996 corrosion skull and crossbones environment DANGER 301 310 315 317 318 330 410 260 273 280 284 301+310 302+350 68 18% 244 mg/kg (oral, rat) Ethylene glycol 1,2-Ethanedithiol 2-Mercaptoethanol is the organosulfur compound with the formula HOCH2CH2SH. It is a colorless liquid. 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 rotten egg odor 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.Kathrin-Maria Roy Thiols and Organic sulphides 2005 10.1002/14356007.a26_767 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. Reactions 2-Mercaptoethanol cleaves disulfide bonds. 2-Mercaptoethanol reacts with aldehydes and ketones to give the corresponding oxathiolanes.1,3-Dithiolanes, 1,3-Dithianes https://www.organic-chemistry.org/protectivegroups/carbonyl/1,3-dithiolanes.htm Organic Chemistry Portal 27 May 2008 https://web.archive.org/web/20080517162047/http://www.organic-chemistry.org/protectivegroups/carbonyl/1%2C3-dithiolanes.htm 17 May 2008 live This makes 2-mercaptoethanol useful as a protecting group, giving a derivative whose stability is between that of a dioxolane and a dithiolane. Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis Giovanni Sartori Roberto Ballini Franca Bigi Giovanna Bosica Raimondo Maggi Paolo Righi Chem. Rev. 2004 104 1 199–250 10.1021/cr0200769 14719975 400px|Reaction scheme for the formation of oxathiolanes by reaction of 2-mercaptoethanol with aldehydes or ketones. Like most alkylthiols, it adds to Michael acceptors such as acrylonitrile.β-(2-Hydroxyethylmercapto)propionitrile Organic Syntheses 1949 29 52 10.15227/orgsyn.029.0052 free Leon L. Gershbein Applications Reducing proteins Some proteins are denatured by 2-mercaptoethanol. In the case of excess 2-mercaptoethanol, the following equilibrium is shifted to the right: RS–SR + 2 HOCH2CH2SH 2 RSH + HOCH2CH2S–SCH2CH2OH 400px|Reaction scheme for the cleavage of disulfide bonds by 2-mercaptoethanol By breaking the S-S bonds, both the tertiary structure and the quaternary structure of some proteins can be disrupted.http://www.chemicalland21.com/specialtychem/finechem/2-MERCAPTOETHANOL.htm Chemicalland21.com 2-Mercaptoethanol 8 October 2006 https://web.archive.org/web/20061005223640/http://www.chemicalland21.com/specialtychem/finechem/2-MERCAPTOETHANOL.htm 2006-10-05 usurped 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.Aitken CE Marshall RA, Puglisi JD An oxygen scavenging system for improvement of dye stability in single-molecule fluorescence experiments Biophys J 94 5 1826–35 2008 17921203 10.1529/biophysj.107.117689 2242739 2008BpJ....94.1826A 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.Yeh, J. I. (2009) "Additives and microcalorimetric approaches for optimization of crystallization" in Protein Crystallization, 2nd Edition (Ed: T. Bergfors), International University Line, La Jolla, CA. 978-0-9720774-4-6.Stevens R. Stevens L. Price N.C. The Stabilities of Various Thiol Compounds used in Protein Purifications Biochemical Education 1983 11 2 70 10.1016/0307-4412(83)90048-1 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. 3921014 1144764 1985 Verduyn C Properties of the NAD(P)H-dependent xylose reductase from the xylose-fermenting yeast Pichia stipitis The Biochemical Journal 226 3 669–77 Van Kleef R Frank J Schreuder H Van Dijken J. P. Scheffers W. A. 10.1042/bj2260669 Denaturing ribonucleases 2-Mercaptoethanol is used in some RNA isolation procedures to eliminate ribonuclease released during cell lysis. Numerous disulfide bonds make ribonucleases very stable enzymes, so 2-mercaptoethanol is used to reduce these disulfide bonds and irreversibly denature the proteins. This prevents them from digesting the RNA during its extraction procedure.Nelson, David R. Lehninger, Albert L Cox, Michael Lehninger principles of biochemistry 2005 W.H. Freeman New York 0-7167-4339-6 148 https://archive.org/details/lehningerprincip00lehn_0/page/148 Deprotecting carbamates Some carbamate protecting groups such as carboxybenzyl (Cbz) or allyloxycarbonyl (alloc) can be deprotected using 2-mercaptoethanol in the presence of potassium phosphate in dimethylacetamide.Scattolin Thomas Gharbaoui Tawfik Chen Cheng-yi A Nucleophilic Deprotection of Carbamate Mediated by 2-Mercaptoethanol Organic Letters 2022 24 20 3736–3740 10.1021/acs.orglett.2c01410 35559611 248776636 Genetic transformation DNA uptake in Escherichia coli can be facilitated by the addition of 2-mercaptoethanol in genetic transformation.How can I increase transformation efficiency? NEB https://www.neb.com/en-gb/faqs/0001/01/01/how-can-i-increase-transformation-efficiency 2025-08-19 www.neb.com Safety 2-Mercaptoethanol is moderately toxic and is an irritant to skin and eyes. Material Safety Data Sheet https://www.sigmaaldrich.com/DE/en/sds/sigma/m3148 Merck 24 September 2023 Knight J. Jonathan Encyclopedia of Reagents for Organic Synthesis 2-Mercaptoethanol 2001 10.1002/047084289X.rm026 0-471-93623-5 See also Dithiothreitol (DTT) Dithiobutylamine (DTBA) TCEP References Category:Thiols Category:Primary alcohols Category:Reducing agents Category:Foul-smelling chemicals