PRODUCTS

2-MERCAPTOETHANOL

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.

CAS No. : 60-24-2
EC No. : 200-464-6

Synonyms:
Thioethylene glycol; Thioglycol; β-Mercaptoethanol; 2-Hydroxyethylmercaptan; BME; Thioethylene glycol; 2-ME; 2-Sulfanylethan-1-ol[1]; 2-Mercaptoethan-1-ol; 2-Hydroxy-1-ethanethiol; β-Mercaptoethanol; Thioglycol; Beta-merc; 2-mercaptoethanol; Mercaptoethanol; 60-24-2; Beta-Mercaptoethanol; Thioglycol; Ethanol, 2-mercapto-; 2 Mercaptoethanol; 2-Sulfanylethanol; 2-Thioethanol; Thioethylene glycol; Thiomonoglycol; 2-Hydroxyethanethiol; 2-Hydroxyethyl mercaptan; 2-Hydroxy-1-ethanethiol; Monothioglycol; 2-Mercapto-1-ethanol; 1-Ethanol-2-thiol; Hydroxyethyl mercaptan; Monothioethylene glycol; 2-Mercaptoethyl alcohol; 2-ME; Mercaptoetanol; Ethylene glycol, monothio-; 1-Hydroxy-2-mercaptoethane; 1-Mercapto-2-hydroxyethane; 2-Hydroxyethylmercaptan; Emery 5791; USAF EK-4196; Monothioethyleneglycol; beta-Hydroxyethanethiol; 2-sulfanylethan-1-ol; .beta.-Mercaptoethanol; .beta.-Hydroxyethanethiol; beta-Hydroxyethylmercaptan; 2-mercapto ethanol; CCRIS 2097; BME; Thioethyleneglycol; Thioglycol; β-Mercaptoethanol; Hydroxyethyl mercaptan; 2-MERCAPTOETHANOL; 2-Mercaptoethanol; EINECS 200-464-6; UN2966; .beta.-Hydroxyethylmercaptan; betamercaptoethanol; 2-Mercaptoethanol, 99%, pure; 2-Mercaptoethanol, >=99.0%; 2mercaptoethanol; b-mercaptoethanol; ethylene thioglycol; 2-mercapto-ethanol; 2-sulfanyl-ethanol; 2-ME; beta-sulfanylethanol; hydroxyethyl sulfide; mercaptoethyl alcohol; 2-Sulfanylethanol #; 2-hydroxy-ethanethiol; 2-Hydroxyethanethiol;; 2-mercaptoethan-1-ol; HSCH2CH2OH; [O]CCS; OCC[S]; WLN: SH2Q; EC 200-464-6; 4-01-00-02428 (Beilstein Handbook Reference); Thioglycol [UN2966] [Poison]; NSC-3723; Thioglycol [UN2966] [Poison]; ZINC8216595; 2-Mercaptoethanol[forElectrophoresis]; STL482546; 2-Mercaptoethanol, for electrophoresis; 2-Mercaptoethanol, for synthesis, 99.0%; 2-Mercaptoethanol, SAJ special grade, >=99.0%; 3-Pyridinecarbonitrile, 4-methyl-2,6-di-5-morpholinyl-; 2-Mercaptoethanol, for HPLC derivatization, >=99.0% (GC); 2-Mercaptoethanol, BioUltra, for molecular biology, >=99.0% (GC); 2-Mercaptoethanol, for molecular biology, for electrophoresis, suitable for cell culture, BioReagent, 99% (GC/titration); 2-Mercaptoethanol, PharmaGrade, Manufactured under appropriate controls for use as raw material in pharma or biopharmaceutical production.

2-Mercaptoethanol

Properties of 2-Mercaptoethanol
Chemical formula 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) 1.4996

Production of 2-Mercaptoethanol
2-Mercaptoethanol is manufactured industrially by the reaction of ethylene oxide with hydrogen sulfide. Thiodiglycol and various zeolites catalyze the reaction.

Reaction of ethylene oxide with hydrogen sulfide to form 2-mercaptoethanol in the presence of thiodiglycol as solvent and catalyst.

Reactions of 2-Mercaptoethanol
2-Mercaptoethanol reacts with aldehydes and ketones to give the corresponding oxathiolanes. This makes 2-mercaptoethanol useful as a protecting group, giving a derivative whose stability is between that of a dioxolane and a dithiolane.

Reaction scheme for the formation of oxathiolanes by reaction of 2-mercaptoethanol with aldehydes or ketones.

Applications of 2-Mercaptoethanol
Reducing proteins
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:

RS–SR + 2 HOCH2CH2SH ⇌ 2 RSH + HOCH2CH2S–SCH2CH2OH
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. 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.

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.

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.

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.

Safety of 2-Mercaptoethanol
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.

Molar Mass: 78.13 g/mol
CAS #: 60-24-2
Hill Formula: C₂H₆OS
Chemical Formula: HSCH₂CH₂OH
EC Number: 200-464-6

General description of 2-Mercaptoethanol
2-mercaptoethanol is a thiol compound, commonly used as a reducing agent in organic reactions.

Packaging
1, 2.5 L in glass bottle
10, 100, 250, 500 mL in glass bottle

Application
2-mercaptoethanol is widely used for retarding oxidation of biological compounds in solution.

Description of 2-Mercaptoethanol
Gibco 2-Mercaptoethanol (also known as beta-mercaptoethanol or BME) is a potent reducing agent used in cell culture media to prevent toxic levels of oxygen radicals. 2-Mercaptoethanol is not stable in solution, so most protocols require daily supplementation. Gibco 2-Mercaptoethanol contains 2-mercaptoethanol at a concentration of 55 mM in Dulbecco's phosphate buffered saline (DPBS).

hipping Condition: Room Temperature
Cell Type: Mammalian
Form: Liquid
Reagent Type: Dulbecco's Phosphate Buffered Saline
Shelf Life: 36 Months
Solution Type: 2-Mercaptoethanol
pH: 6 to 8
Product Type: Supplement

Description of 2-Mercaptoethanol
Thermo Scientific Pierce 2-Mercaptoethanol (2-ME), also called beta-mercaptoethanol (b-ME), is a mild reducing agent for cleaving protein disulfide bonds.

Features of 2-mercaptoethanol:

• Also known as β-mercaptoethanol, beta-mercaptoethanol, bME, b-ME
• Mild but effective reducing agent, often included in enzyme solutions to protect against catalytic site inactivation due to cysteine sulfhydryl oxidation/disulfide formation; added at final concentrations of 5 and 20 mM, with or without EDTA, as an additional protectant

About 2-mercaptoethanol

2-mercaptoethanol is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 to < 10 000 tonnes per annum.

2-mercaptoethanol is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Widespread uses by professional workers
2-mercaptoethanol is used in the following products: pH regulators and water treatment products and laboratory chemicals. 2-mercaptoethanol is used in the following areas: health services and scientific research and development. Other release to the environment of 2-mercaptoethanol is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).

Uses at industrial sites
2-mercaptoethanol is used in the following products: pH regulators and water treatment products and metal surface treatment products.
2-mercaptoethanol has an industrial use resulting in manufacture of another substance (use of intermediates).
2-mercaptoethanol is used in the following areas: mining and formulation of mixtures and/or re-packaging.
2-mercaptoethanol is used for the manufacture of: chemicals.
Release to the environment of 2-mercaptoethanol can occur from industrial use: as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites, as processing aid and as processing aid.

Manufacture
Release to the environment of 2-mercaptoethanol can occur from industrial use: manufacturing of the substance.

Base-catalyzed cleavage of epoxides with hydrogen sulfide gives mercaptoalcohols. Symmetrical bis(1-hydroxyalkyl) sulfides are formed as byproducts. Inorganic bases, amines and anion exchange resins, zeolites, or guanidine can be used as catalysts. In industry, preparation of mercaptoethanol by addition of H2S to ethylene oxide is catalyzed by either a cation exchange resin or the byproduct thiodiglycol.

Gas-liquid chromatographic determination of 2-mercaptoethanol.

The major hazards encountered in the use and handling of 2-mercaptoethanol stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, dermal contact), exposure to this water-white liquid, with a strong disagreeable odor, may occur from its use as a solvent for dyestuffs and as a chemical intermediate in the production of pharmaceuticals, rubber chemicals, flotation agents, biochemical reagents, insecticides, plasticizers, reducing agents, PVC stabilizers, and agricultural chemicals. Effects from exposure may include irritation of the eyes, nose, and skin, headache, dizziness, urinary disturbances, pulmonary edema, and respiratory distress or failure. In activities and situations where over-exposure may occur, wear a positive pressure self-contained breathing apparatus, and protective clothing. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Contaminated clothing and shoes should be removed at the site. While 2-mercaptoethanol does not ignite easily, it may burn with the production of poisonous gases. For fires involving this substance, extinguish withdry chemical, CO2, water spray, fog, or regular foam. Small spills of this substance may be taken up with sand or other noncombustible absorbent and placed into containers for later disposal. Large spills should be diked far ahead of the spill for later disposal.

A reduction in SCE frequency was observed when cells were cultured with 20 microM 2-Mercaptoethanol (2-ME )and IL-2 compared to interleukin-2 (IL-2) alone. Three nuclear proteins, with relative molecular masses of approximately 13,000-18,000, 20,000, and 80,000, were phosphorylated in IL-2-exposed G1-phase nuclei. Elicitation of these nuclear proteins in IL-2-exposed cells was not affected by exposure to 2-ME.

2-Mercaptoethanol induced arteriosclerosis and endothelial cell cytotoxicity in baboons were inhibited by sulfinpyrazone.

Acute Exposure/ 2-Mercaptoethanol applied undiluted to the rabbit eye is toxic to the conjunctiva and causes long-lasting moderately severe corneal opacity.

Chronic Exposure or Carcinogenicity/ Female RLEF1/Lati rats were chronically treated with 2-mercaptoethanol in a dose of 13 micrograms/100 g bw-1/day-1 dissolved in drinking water. During a 48-h experiment 15N-labelled glycine was given orally in a dose of 5 mg 15N.kg bw-1 and urine samples were collected and analysed by an emission spectrometric isotope method. Protein synthesis and nitrogen excretion rate constants were calculated according to the three-pool model, and 3-methylhistidine excretion rates were also determined. 2-Mercaptoethanol appears to influence protein metabolism; however, the slower rates of protein synthesis proved to be apparent in almost all groups of treated rats. Protein synthesis and nitrogen excretion rate constants have exceptionally high values in 2-year-old rats, possibly explained by the occurrence of hypercompensation mechanisms in old age. These were reflected by the excretion rates of 3-methylhistidine which were reduced as a result of sulphhydryl group interactions in age-dependent cellular metabolic changes.

Chronic Exposure or Carcinogenicity/ In old CBA/Ca mice the effect of cigarette smoke was compared with that of 2-mercaptoethanolrcaptoethanol (2-ME) treatment. It could be stated that spontaneous death was more frequent in animals kept in cigarette smoke than in the control animals. Prevalence of hepatocellular carcinoma was higher in animals kept in cigarette smoke than in the controls. After 2-mercaptoethanol treatment the occurrence of hepatocellular carcinoma was significantly lower and animals without disorders were more frequent than in smokers. Body weights were lower in animals kept in cigarette smoke and differences in organ indices could be observed, too. Immunological changes were also demonstrated: in mice kept in cigarette smoke the reactivity against a foreign antigen such as sheep erythrocytes (SRBC) was lower, while after 2-mercaptoethanol treatment it was higher than in their controls using direct plaque formation technique. The ratio of normal reactivity (against SRBC) and autoreactivity (against mouse erythrocytes) showed a decrease in smoker animals, and an increase in the 2-mercaptoethanol-treated ones. The experiments showed a deleterious effect of cigarette smoke and a beneficial effect of 2-mercaptoethanol on age-related alterations.

2-Mercaptoethanol's production and use as solvent for dyestuffs, intermediate for producing dyestuffs, pharmaceuticals, rubber chemicals, flotation agents, insecticides, plasticizers, water-soluble reducing agent, biochemical reagent, PVC stabilizers, agricultural chemicals, and textile auxiliary may result in its release to the environment through various waste streams. It is a hydrolysis product of the chemical warfare agent mustard gas. 2-Mercaptoethanol is formed through the decomposition of naturally occurring products such as swine manure and proteins (produced by marine algae and other marine plants). If released to air, an extrapolated vapor pressure of 1.76 mm Hg at 25 °C indicates 2-mercaptoethanol will exist solely as a vapor. Vapor-phase 2-mercaptoethanol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 8.5 hours. 2-Mercaptoethanol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight.

If released to soil, 2-mercaptoethanol is expected to have very high mobility based upon an estimated Koc of 1.3. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.8X10-7 atm-cu m/mole. 2-Mercaptoethanol may volatilize from dry soil surfaces based upon its vapor pressure. A 29% biomineralization after 55 days under methanogenic conditions indicates that biodegradation is not an important environmental fate process in anoxic environments. If released into water, 2-mercaptoethanol is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3.0 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 2-mercaptoethanol may occur through inhalation and dermal contact with this compound at workplaces where 2-mercaptoethanol is produced or used. Monitoring data indicate that the general population may be exposed to 2-mercaptoethanol via dermal contact with this compound and other products containing 2-mercaptoethanol.

2-Mercaptoethanol has been identified as one of volatile substances evolved from aerobic and anaerobic microbial decomposition of liquid swine manure.

2-Mercaptoethanol's production and use as a solvent for dyestuffs, intermediate for producing dyestuffs, pharmaceuticals, rubber chemicals, flotation agents, insecticides, plasticizers, water-soluble reducing agent, biochemical reagent, PVC stabilizers, agricultural chemicals, and textile auxiliary may result in its release to the environment through various waste streams. 2-Mercaptoethanol is a hydrolysis product of the chemical warfare agent mustard gas.

Based on a classification scheme, an estimated Koc value of 1.3, determined from a structure estimation method, indicates that 2-mercaptoethanol is expected to have very high mobility in soil. Volatilization of 2-mercaptoethanol from moist soil surfaces is not expected to be an important fate process given an estimated Henry's Law constant of 1.8X10-7 atm-cu m/mole, derived from its extrapolated vapor pressure, 1.76 mm Hg, and an assigned value for water solubility of 1.00X10+6 mg/L (miscible). 2-Mercaptoethanol is expected to volatilize from dry soil surfaces based upon its vapor pressure. A 29% biomineralization after 55 days under methanogenic conditions(5) indicates that biodegradation is not an important environmental fate process in anoxic soil environments.

According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere, 2-mercaptoethanol, which has an extrapolated vapor pressure of 1.76 mm Hg at 25 °C, is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-mercaptoethanol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 8.5 hours, calculated from its rate constant of 4.6X10-11 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method. 2-Mercaptoethanol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight.

2-Mercaptoethanol, was shown to be biomineralized under methanogenic conditions. 2-Mercaptoethanol, present at 100 mg/L reached 29% biodegradation in 55 days using 120 mL flasks containing sludge from an upflow anaerobic blanket reactor treating liquid hen manure at 1 g volatile suspended solids (VSS)/L, 0.4 g Chemical Oxygen Demand (COD), basal medium, and incubated at 30 °C. Therefore, this compound is not expected to biodegrade rapidly under anaerobic conditions. Addition of cosubstrates, glucose or a combination of propionic or butyric acids, did not affect the rate of degradation. The compound is moderately toxic to microorganisms.

The rate constant for the vapor-phase reaction of 2-mercaptoethanol with photochemically-produced hydroxyl radicals has been estimated as 4.6X10-11 cu cm/molecule-sec at 25 °C using a structure estimation method. This corresponds to an atmospheric half-life of about 8.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm. The rate constant for the reaction between hydroxyl radicals and 2-mercaptoethanol in aqueous solution at pH 6.5 has been experimentally determined to be 6.8X10+9/M-sec; assuming that the hydroxyl radical concentration of brightly sunlit natural water is 1X10-17 M, the half-life for this reaction would be 118 days. 2-Mercaptoethanol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups. 2-Mercaptoethanol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight.

An estimated BCF of 3.0 was calculated for 2-mercaptoethanol, using an estimated log Kow of -0.20 and a regression-derived equation. According to a classification scheme, this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Using a structure estimation method based on molecular connectivity indices, the Koc of 2-mercaptoethanol can be estimated to be 1.3. According to a classification scheme, this estimated Koc value suggests that 2-mercaptoethanol is expected to have very high mobility in soil.

The Henry's Law constant for 2-mercaptoehtanol is estimated as 1.8X10-7 atm-cu m/mole derived from its vapor pressure, 1.76 mm Hg, and an assigned value for water solubility of 1.00X10+6 mg/L (miscible). This Henry's Law constant indicates that 2-mercaptoethanol is expected to be essentially nonvolatile from water surfaces. 2-Mercaptoethanol's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may not occur. 2-Mercaptoethanol is expected to volatilize from dry soil surfaces based upon its extrapolated vapor pressure.

NIOSH (NOES Survey 1981-1983) has statistically estimated that 14,140 workers (4,607 of these are female) are potentially exposed to 2-mercaptoethanol in the US. Occupational exposure to 2-mercaptoethanol may occur through inhalation and dermal contact with this compound at workplaces where 2-mercaptoethanol is produced or used. Monitoring data indicate that the general population may be exposed to 2-mercaptoethanol via dermal contact with this compound and other products containing 2-mercaptoethanol.

2-Mercaptoethanol concentrations of 0.01 ppb or less were detected in samples of German wines.

2-Mercaptoethanol and other thiol concentrations of less than 100 uM were detected in intertidal marine sediments from Biscayne Bay, FL; the presence of the thiols was attributed to protein degradation, where the protein source was marine algae and other higher plants.

2-Mercaptoethanol solution has a concentration of approx. 14.3 M.

Quality Level      200
vapor density      2.69 (vs air)
vapor pressure      1 mmHg ( 20 °C)
assay      ≥99.0%
expl. lim.      18 %
concentration      14.3 M (pure liquid)
refractive index      n20/D 1.500 (lit.)
bp      157 °C (lit.)
density      1.114 g/mL at 25 °C (lit.)
storage temp.      2-8°C
SMILES string      OCCS
InChI      1S/C2H6OS/c3-1-2-4/h3-4H,1-2H2
InChI key      DGVVWUTYPXICAM-UHFFFAOYSA-N
Show Fewer Properties
Description
General description
2-mercaptoethanol is a thiol compound, commonly used as a reducing agent in organic reactions.

Packaging of 2-Mercaptoethanol
1, 2.5 L in glass bottle

10, 100, 250, 500 mL in glass bottle

Application of 2-Mercaptoethanol
2-mercaptoethanol is widely used for retarding oxidation of biological compounds in solution.

2-Mercaptoethanol is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE at a concentration of 5%. Cleaving intermolecular (between subunits) disulfide bonds allows the subunits of a protein to separate independently on SDS-PAGE. Cleaving intramolecular (within subunit) disulfide bonds allows the subunits to become completely denatured so that each peptide migrates according to its chain length with no influence due to secondary structure.

2-Mercaptoethanol (also known as beta-mercaptoethanol or BME) is a potent reducing agent used in cell culture media to prevent toxic levels of oxygen radicals. 2-Mercaptoethanol is not stable in solution, so most protocols require daily supplementation. 2-Mercaptoéthanol 2-Mercaptoethanol contains 2-mercaptoethanol at a concentration of 55 mM in Dulbecco's phosphate buffered saline (DPBS).
cGMP manufacturing and quality system
2-Mercaptoéthanol Reducing Agent is manufactured at a cGMP compliant facility, located in Grand Island, New York. The facility is registered with the FDA as a medical device manufacturer and is certified to ISO 13485 standards.

Background
2-Mercaptoethanol (2-ME) is a clear colorless to very faint yellow liquid that boils at 157–158 °C and has a concentration of 14.3 M (mol l−1). The bulk product decomposes slowly in air. If kept sealed at room temperature, it will remain pure (more than 99%) up to 3 years. 2-Mercaptoéthanolis miscible in water in all proportions, and miscible in alcohol, ether, and benzene. Solution of 2-Mercaptoéthanolis readily oxidized in air to a disulfide, particularly at high pH values.

It should be remembered that its reaction with strong acids or alkali metals will release flammable hydrogen gas, and it is combustible as a liquid or vapor. 2-Mercaptoéthanolcan be toxic if ingested, and fatal if inhaled or absorbed through the skin. 2-Mercaptoéthanol was found to be more toxic than ethanol to all tissues but showed a significant diminished toxicity upon dilution.

Human Embryonic Stem Cell Culture
Rodolfo Gonzalez, ... Philip H. Schartz, in Human Stem Cell Manual, 2007

2-Mercaptoethanol
2-Mercaptoethanol (2-ME) has been used in ESC culture media since the first derivation of mouse ESCs in 1981. Originally included as a reducing agent because of concern about oxidation of culture components, it continues to be used in hESC media. Since the final concentration is 0.1 mM, and the pure solutions of 2-Mercaptoéthanolare 14.3 M, it is necessary to start ith a stock solution.

Several companies sell diluted solutions of 2-ME; the 55 mM solution in PBS (Invitrogen catalog no. 21985-023) is a convenient concentration for a stock.

If you ish to make your on stock, e suggest that you make a 1000× stock from the generally available concentrated solution (14.3 M).

For 1000× stock: dilute 35 μL of 14.3 M 2-Mercaptoéthanol(Sigma catalog no. M7522) into 5 mL of PBS to make a 0.1 M stock solution. Filter before use.

Properties

Related Categories: Antioxidants and Reducing Agents for Protein Stabilization, Biochemicals and Reagents, Building Blocks, Chemical Synthesis, HIS Select Supporting Products and Reagents,
HIS-Select, Molecular Biology, Organic Building Blocks, Protein Modification, Protein Structural Analysis, Proteins and Derivatives, Proteomics, Purification and Detection, Reagents and Products for use with HIS-Select, Reagents for Protein Stabilization, Reagents for reduction of proteins, Recombinant Protein Expression and Analysis, Reduction and Oxidation, Sulfur Compounds, Thiols/Mercaptans

Molecular Formula:C2H6OS or HSCH2CH2OH
Molecular Weight:78.129 g/mol
InChI Key:DGVVWUTYPXICAM-UHFFFAOYSA-N
vapor density:2.69 (vs air)
vapor pressure:1 mmHg ( 20 °C)
expl. lim. :18 %
concentration:14.3 M (pure liquid)
refractive index: n20/D 1.500(lit.)
bp: 157 °C(lit.)
density: 1.114 g/mL at 25 °C(lit.)
storage temp.: 2-8°C

2-Mercaptoethanol (also ß-mercaptoethanol, BME, 2BME, 2-ME or ß-met) is the chemical compound with the formula HOCH2CH2SH. ME or ßME, 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

2-Mercaptoethanol is one of the most common agents used for disulfide reduction. Sometimes referred to as ß-mercaptoethanol, it is a clear, colorless liquid with an extremely strong odor. All operations with this chemical should be performed in a well-ventilated fume hood. The reduction of protein disulfides with 2-mercaptoethanol proceeds rapidly via a two-step process involving an intermediate mixed disulfide. Due to its strong reducing properties, the reagent is used most often when complete disulfide reduction is required. It can also be used to cleave disulfide-containing crosslinking agents. Usually a concentration of 0.1-M 2-mercaptoethanol will cleave a disulfide-containing crosslinker and liberate conjugated proteins

Reducing proteins

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:

RS-SR + 2 HOCH2CH2SH ? 2 RSH + HOCH2CH2S-SCH2CH2OH
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.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.

Molecules of 2-mercaptoethanol (ME) were spontaneously chemisorbed on silver, copper, and gold surfaces. Surface-enhanced Raman scattering investigation revealed that, as for unsubstituted alkanethiols, the average orientation of the "molecular chain" of ME is the most perpendicular to the metal surface for ME molecules adsorbed on silver. Immersion of an ME-modified electrode in diluted ME solution leads to quick desorption of a portion of the monolayer and an increase in the relative surface concentration of the gauche conformer. The time constant of this rearrangement (below 1 min) is more than 1 order of magnitude shorter than that of monolayers formed from analogous thiols (HS-(CH2)2-X) with X = CH3, NH2, COOH, or SO3Na. The structure of the ME monolayer is highly pH-sensitive, but it is independent of the presence of neutral salts in solutions. In acidic solutions, the surface concentration of a gauche conformer considerably increases. Since protonation of a significant number of hydroxyl groups is unlikely under the conditions used, it is likely that in acidic solutions the kinetics of the desorption and the desorption/adsorption equilibrium are changed. It is probable that desorption of ME as thiol molecules is facilitated because some of the sulfur atoms of ME adsorbed as thiolate are protonated. We also found an analogous effect, although less pronounced, for monolayers self-assembled from propanethiol. This indicates that this mechanism, so far not considered, can also be important for some other (especially short-chain) thiols. In basic solutions, the concentration of a trans conformer increases and probably some of the hydroxyl groups dissociate. For all investigated solutions, the structure of the ME monolayer on gold was found to be less affected by its surroundings than that of monolayers on silver or copper.

2-Mercaptoethanol (also called Thioglycol) is a clear, colorless liquid with disagreeable odor.Beta mercaptoethanol is miscible in water and nearly all common organic solvents.Beta merkapto ethanol is used as a intermediate for the synthesis of PVC heat stabilizers and as a chain transfer agent in the manufacture of PVC. Beta mercapto ethanol is used as a building block to produce corp protection products, dispersants, fibers, textiles, .dyes, and pharmaceuticals. 2 Mercaptoethanol is used as a component of corrosion inhibitors and ore floatation agent. 2 mercaptoethyl alcohol is used in as a raw material for leather and fur industry, cosmetics, hair removal.

2-Mercaptoethanol is often used interchangeably with dithiothreitol (DTT) or the odorless tris(2-carboxyethyl)phosphine (TCEP) in biological applications

Consumer & Industrial Applications

Ink & Dye Additives: We offer hydrocarbon compounds that serve as ink carriers as well as sulfur chemicals that are effective solvents in digital image processing.

Food & Nutrition Applications

To help the agricultural industry flourish in its efforts to maintain fertile land, grow crops and raise healthy livestock, produces agrochemical intermediates such as 2-mercaptoethanol.

Petroleum & Refinery

2-Mercaptoethanol or BME is a highly volatile, yet water soluble material that is widely used in cleaning agents, as a corrosion inhibitor for performance material (pipe) and as a tin stabilizer in PVC production.

Polymers and Rubber Applications

Normal mercaptans are used as reactants in the synthesis of antioxidants, which minimize undesirable effects from processes such as the stabilization of tin.
2-mercaptoethanol is also used as a chain transfer agent in processes where control of molecular weight is critical.

Water Treatment Applications