2-MERCAPTOETHANOL
2-MERCAPTOETHANOL
2-Mercaptoethanol = Beta Mercaptoethanol = Thioglycol = β-Mercaptoethanol
Display Name: 2-mercaptoethanol
EC Number: 200-464-6
EC Name: 2-mercaptoethanol
CAS Number: 60-24-2
Molecular formula: C2H6OS
IUPAC Name: 2-sulfanylethanol
Thioethylene glycol
2-Hydroxyethylmercaptan
BME
β-Mercaptoethanol
Formula : C2H6OS
Molecular Weight : 78.13 g/mol
2-Mercaptoethanol (also β-mercaptoethanol, BME, 2BME, 2-ME or β-met) is the chemical compound with the formula HOCH2CH2SH.
Mercaptoethanol or Beta-mercaptoethanol, as it is commonly abbreviated, is used to reduce disulfide bonds and can act as a biological antioxidant by scavenging hydroxyl radicals (amongst others).
Mercaptoethanol 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.
Mercaptoethanol is a primary alcohol and an alkanethiol.
Synonyms: β-Mercaptoethanol; 2-Hydroxyethylmercaptan; BME; Thioethylene glycol; 2-Hydroxy-1-ethanethiol; Monothioethyleneglycol
2-Mercaptoethanol
2-Mercaptoethanol is a versatile intermediate with a wide range of applications.
2-Mercaptoethanol is mainly used in the production of organo tin stabilizers in the market segment PVC.
2-Mercaptoethanol is used for consumer and industrial applications, food nutrition applications, petroleum refinery, polymers and rubber applications and water treatment applications.
Industries: Agriculture , Inks , Maintenance, Repair, Overhaul , Water Treatment
2-Mercaptoethanol is used as a chain transfer agent in polymers and rubber applications.
2-Mercaptoethanol is also used as ink and dye additives for consumer and industrial applications.
Moreover, 2- Mercaptoethanol is highly volatile, yet soluble material that is used in cleaning agents, as corrosion inhibitor and as in tin stabilizer in PVC production.
2-Mercaptoethanol is an agrochemical intermediate used in food and nutritional applications to maintain fertile land and raise healthy livestock
Preferred IUPAC name: 2-Sulfanylethan-1-ol
Other names
2-Mercaptoethan-1-ol
2-Hydroxy-1-ethanethiol
β-Mercaptoethanol
Thioglycol
Beta-merc
2-Hydroxyethylmercaptan ; β-Mercaptoethanol; BME; Thioethylene glycol; 2-Hydroxy-1-ethanethiol; Monothioethyleneglycol ; 1-ethane-2-thiol; thioglycol ; 2-ME; b-ME; 2-thioethanol
2-Mercaptoethanol is used to reduce disulfide linkages in solubilizing proteins for gel electrophoresis (typically used in SDS-PAGE sample buffer at 5% concentration).
Also Mercaptoethanol reduces excess oxidative polymerization of catalysts.
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.
In solution, 2-mercaptoethanol is readily oxidized in air to a disulfide, especially at alkaline pH.
Because of this property, Mercaptoethanol is widely used to protect proteins, enzymes in particular, from becoming inactive.
An excess of 2-mercaptoethanol (generally used at 0.01 M) will maintain the protein thiol groups in their reduced state.
Synonyms : 1-ethanol-2-thiol / 1-hydroxy-2-mercaptoethane / 1-mercapto-2-hydroxyethane / 2-hydroxy-1-
ethanethiol / 2-hydroxyethanethiol / 2-hydroxyethyl mercaptan / 2-ME / 2-mercapto-1-ethanol /
2-mercaptoethanol / 2-mercaptoethyl alcohol / 2-thioethanol / beta-hydroxyethanethiol / betahydroxyethylmercaptan / beta-mercaptoethanol / BME / emery 5791 / ethanol, 2-mercapto- /
ethylene glycol, monothio- / ethylene thioglycol / hydroxyethyl mercaptan / mercapto-2 ethanol /
METH / monothioethyleneglycol / monothioglycol / thioethylene glycol / thioglycol /
thiomonoglycol / USAF EK-4196
2-Mercaptoethanol (also called Thioglycol) is a clear, colorless liquid with disagreeable odor.
Mercaptoethanol is miscible in water and nearly all common organic solvents.
Mercaptoethanol is produced by reaction of hydrogen sulphide gas and ehtylene oxide.
Mercaptoethanol is used as a intermediate for the synthesis of PVC heat stabilizers and as a chain transfer agent in the manufacture of PVC.
Mercaptoethanol 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.
In biochemistry, 2-mercaptoethanol is studied in the activity of immune system or denatures the proteins due to its strong reducing properties.
Low molecular weight thiols or their esters such as 2-mercaptoethanol, 1-thioglycerol and dithiothreitol denatures the proteins by reducing disulfide linkages leading to tautomerization and breaking up quaternary protein structure.
They have been studied as anti-cancer agents by acting as alkylating agents to damage the cancer cell DNA.
Identifiers
CAS Number: 60-24-2
EC Number: 200-464-6
UN number: 2966
Properties
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
2-Mercaptoethanol
2-Mercaptoethanol
IUPAC name 2-Hydroxy-1-ethanethiol
Other names 2-Mercaptoethanol
Thioglycol
β-Mercaptoethanol
Identifiers
CAS number 60-24-2
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.
Mercaptoethanol 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) .
Mercaptoethanol 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.
Mercaptoethanol is prepared by the action of hydrogen sulfide on ethylene oxide.
2-Mercaptoethanol 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, 2-Mercaptoethanol will remain pure (more than 99%) up to 3 years.
2-Mercaptoethanol is miscible in water in all proportions, and miscible in alcohol, ether, and benzene.
Solution of 2-Mercaptoethanol is 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-Mercaptoethanol can be toxic if ingested, and fatal if inhaled or absorbed through the skin.
2-Mercaptoethanol was found to be more toxic than ethanol to all tissues but showed a significant diminished toxicity upon dilution.
2-Mercaptoethanol is used to reduce disulfide bonds and can act as a biological antioxidant by scavenging hydroxyl radicals. 2-Merceptoethanol is used to reduce disulfide linkages in solubilizing proteins for gel electrophoresis. 2-mercaptoethanol is readily oxidized in air to a disulfide, especially at alkaline pH. Because of this property, it is widely used to protect proteins, enzymes in particular, from becoming inactive. An excess of 2-mercaptoethanol (generally used at 0.01 M) will maintain the protein thiol groups in their reduced state.
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. 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.
Note for Electrophoresis Use: Researchers have seen artifactual bands in SDS-PAGE systems, appearing in the range of 54 to 68 kDa, particularly in 2-dimensional electrophoresis systems when sensitive staining techniques are used to detect proteins, such as gold or silver staining. Although these have appeared when 2-mercaptoethanol is used, they have been attributed to the action of 2-mercaptoethanol on some component in the system. These bands may be eliminated by removing the 2-mercaptoethanol from the protein sample during equilibration and replacing it by iodoacetamide, which reportedly improves recovery and detection of proteins.
Miscible with water, alcohol, ether and benzene. This product typically gives clear solutions when diluted 1:1 in water or diluted 2:1 in 1 M Tris buffer.
2-Mercaptoethanol is used to reduce disulfide bonds and can act as a biological antioxidant by scavenging hydroxyl radicals. 2-Merceptoethanol is used to reduce disulfide linkages in solubilizing proteins for gel electrophoresis. 2-mercaptoethanol is readily oxidized in air to a disulfide, especially at alkaline pH. Because of this property, it is widely used to protect proteins, enzymes in particular, from becoming inactive. An excess of 2-mercaptoethanol (generally used at 0.01 M) will maintain the protein thiol groups in their reduced state.
2-Mercaptoethanol (BME)
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, Chevron Phillips Chemical produces agrochemical intermediates such as 2-mercaptoethanol.
Petroleum & Refinery
2ME 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
2ME 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.
Applications
Additives
Agrochemicals
Antioxidants
Oilfield
Polymers
Water Treatment
Production
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
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
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.[7]
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 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.[11]
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.[1
2-mercaptoethanol
Mercaptoethanol
60-24-2
Beta-Mercaptoethanol
Thioglycol
Ethanol, 2-mercapto-
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
Ethylene glycol, monothio-
1-Hydroxy-2-mercaptoethane
1-Mercapto-2-hydroxyethane
2-Hydroxyethylmercaptan
Emery 5791
USAF EK-4196
2-sulfanylethan-1-ol
.beta.-Mercaptoethanol
.beta.-Hydroxyethanethiol
NSC 3723
UNII-14R9K67URN
2-mercapto ethanol
MFCD00004890
.beta.-Hydroxyethylmercaptan
14R9K67URN
DTXSID4026343
CHEBI:41218
betamercaptoethanol
2-Mercaptoethanol-1,1,2,2-d4
Mercaptoetanol
Monothioethyleneglycol
2-Mercaptoethanol, 99%, pure
2-Mercaptoethanol, >=99.0%
beta-Hydroxyethanethiol
beta-Hydroxyethylmercaptan
CCRIS 2097
284474-53-9
HSDB 5199
EINECS 200-464-6
UN2966
BRN 0773648
2mercaptoethanol
AI3-07710
b-mercaptoethanol
ethylene thioglycol
2-mercapto-ethanol
2-sulfanyl-ethanol
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)
DivK1c_000784
BDBM7971
CHEMBL254951
HMS502H06
KBio1_000784
NSC3723
NINDS_000784
NSC-3723
Thioglycol [UN2966] [Poison]
ZINC8216595
STL482546
2-Mercaptoethanol, for electrophoresis
AKOS000118900
CCG-231050
DB03345
MCULE-2252943288
UN 2966
IDI1_000784
BP-21398
2-Mercaptoethanol, for synthesis, 99.0%
2-Mercaptoethanol, SAJ special grade, >=99.0%
A832651
Q411084
Q-200296
3-Pyridinecarbonitrile, 4-methyl-2,6-di-5-morpholinyl-
F0001-1577
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.
Hazards
GHS pictograms GHS05: Corrosive GHS06: Toxic GHS09: Environmental hazard
GHS Signal word Danger
GHS hazard statements H301, H310, H315, H317, H318, H330, H410
GHS precautionary statements P260, P273, P280, P284, P301+310, P302+350
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]
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.
Thioglycol appears as a water-white liquid. May be toxic by ingestion, inhalation, or skin absorption.
Reducing agent – 2-Mercaptoethanol
The addition of a reducing agent to an assay may be important to prevent the oxidation of cysteines in the proteins being studied and thus the formation of disulfides. The most commonly used reducing agents are dithiothreitol (DTT), β-mercaptoethanol (β-ME) and tris(2-carboxyethyl)phosphine (TCEP).
2-mercaptoethanol or β-mercaptoethanol or BME is a chemical compound of the formula HOCH2CH2SH, a “hybrid” of ethylene glycol and ethanedithiol. At room temperature it is a liquid with a foul-smelling odor. The presence of the thiol -SH function makes 2-mercaptoethanol a reducing agent widely used in biochemistry to protect proteins against oxidation.
The denaturation of proteins requires the reduction of disulfide bridges, which are crucial for the tertiary or quaternary structure of certain proteins. It is commonly used to reduce disulfide bridges present in proteins and can play a role as a biological antioxidant. It is also used because of its hydroxyl group, which makes it miscible in water and reduces the volatility (and therefore the odor) of thiol.
2-Mercaptoethanol is a powerful reducing agent used in cell culture media to prevent toxic levels of oxygen radicals.
Synonyms: 2-Hydroxyethyl mercaptan , 1,1,2,2-tetradeuterio-1-deuteriooxy-2-deuteriosulfanylethane , beta-Mercaptoethanol , β-Mercaptoethanol , β-Hydroxyethanethiol
2-Merceptoethanol is used to reduce disulfide bonds and can act as a biological antioxidant by scavenging hydroxyl radicals. 2-Merceptoethanol is used to reduce disulfide linkages in solubilizing proteins for gel electrophoresis. 2-mercaptoethanol is readily oxidized in air to a disulfide, especially at alkaline pH. Because of this property, it is widely used to protect proteins, enzymes in particular, from becoming inactive. An excess of 2-mercaptoethanol (generally used at 0.01 M) will maintain the protein thiol groups in their reduced state.
2-Merceptoethanol is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE. 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.
Note for Electrophoresis Use: Researchers have seen artifactual bands in SDS-PAGE systems, appearing in the range of 54 to 68 kDa, particularly in 2-dimensional electrophoresis systems when sensitive staining techniques are used to detect proteins, such as gold or silver staining. Although these have appeared when 2-mercaptoethanol is used, they have been attributed to the action of 2-mercaptoethanol on some component in the system. These bands may be eliminated by removing the 2-mercaptoethanol from the protein sample during equilibration and replacing it by iodoacetamide, which reportedly improves recovery and detection of proteins.
Miscible with water, alcohol, ether and benzene. This product typically gives clear solutions when diluted 1:1 in water or diluted 2:1 in 1 M Tris buffer.
2-Merceptoethanol is used to reduce disulfide bonds and can act as a biological antioxidant by scavenging hydroxyl radicals. 2-Merceptoethanol is used to reduce disulfide linkages in solubilizing proteins for gel electrophoresis. 2-mercaptoethanol is readily oxidized in air to a disulfide, especially at alkaline pH. Because of this property, it is widely used to protect proteins, enzymes in particular, from becoming inactive. An excess of 2-mercaptoethanol (generally used at 0.01 M) will maintain the protein thiol groups in their reduced state.
β-Mercaptoethanol can act as an enzyme reactivator in systems necessitating reduction for activation, and has been commonly used to reduce disulfide bonds in order to separate protein subunits for use in electrophoresis. This product can also be used to form o-Phthalaldehyde-beta-mercaptoethanol (OPAME), a fluorogenic reagent shown to detect amino acids based on its reaction with primary amines. More recently OPAME has been used to distinguish between ssDNA/dsDNA and even single base mismatches in the hybridization of DNA.
Applications
Solubilizes proteins by reducing disulfide linkages2-Mercaptoethanol is used in the preparation of nano-graphene for cellular imaging and drug delivery as well as multifunctional polymeric micelle. It acts as a reducing agent used in electrophoresis, amino acid detection, and distinguishing ssDNA/dsDNA. It is also employed as a standard buffer. It is also used in the preparation of PVC heat stabilizers and as a chain transfer agent in the manufacture of PVC. Further, it is used in some RNA isolation procedures to eliminate ribonuclease. It is utilized as a corrosion inhibitor and ore floatation agent. In biochemistry, it is useful to study the activity of the immune system.
Notes
Hygroscopic. Air sensitive and heat sensitive. Incompatible with metals, strong acids, heavy metal salts and oxidizing agents. Store in a cool place.
Product Specifications
– Flash point : 68,3 °C
– Method: Tag closed cup
– Lower explosion limit : 2,3 %(V)
– Upper explosion limit : 18 %(V)
– Oxidizing properties : No
– Autoignition temperature : 295 °C estimated
– Molecular formula : HSCH2CH2OH
– Boiling point/boiling range : 155 – 160 °C
– Vapor pressure : 5,70 MMHG at 37,8 °C
– Relative density : 1,12 at 15,6 °C (60,1 °F)
– Density : 1,12 G/ML
– Partition coefficient: noctanol/water: Pow:0,56
– Viscosity, dynamic : 3,42 cP
– Relative vapor density : 2,69 (Air = 1.0)
– Evaporation rate : 1
– Percent volatile : > 99 %
Primary Chemistry: 2- Mercaptoethanol
Applications: Ink & Dye Additives, Water Treatment, Agrochemical Intermediates, Oilfield, Antioxidant Intermediates, Polymer Modifiers
200-464-6 [EINECS]
2-Hydroxyethylmercaptan
2-Mercaptoethanol [Wiki]
2-Sulfanylethanol [ACD/IUPAC Name]
2-Sulfanylethanol [German] [ACD/IUPAC Name]
2-Sulfanyléthanol [French] [ACD/IUPAC Name]
2-sulfhydryl-ethanol
60-24-2 [RN]
Ethanol, 2-mercapto- [ACD/Index Name]
mercaptoethanol [Wiki]
mercaptoethyl alcohol
MFCD00004890 [MDL number]
Monothioethylene glycol
Monothioethyleneglycol
thioethylene glycol
β-Hydroxyethanethiol
β-Hydroxyethylmercaptan
β-mercaptoethanol
β-Mercaptoethanol
&β;-mercaptoethanol
(2S,3S)-1,4-dimercaptobutane-2,3-diol
1,1,2,2-tetradeuterio-1-deuteriooxy-2-deuteriosulfanylethane
155-04-4 [RN]
155613-89-1 [RN]
1-Ethanol-2-thiol
1-Hydroxy-2-mercaptoethane
1-Mercapto-2-hydroxyethane
2 Mercaptoethanol
2,3-DIHYDROXY-1,4-DITHIOBUTANE
203645-37-8 [RN]
284474-53-9 [RN]
2-Hydroxy-1-Ethanethiol
2-Hydroxyethanethiol
2-Hydroxyethyl mercaptan
2-mercapto ethanol
2-Mercapto-1-ethanol
2-Mercaptobenzothiazole zinc salt
2-Mercaptoethanol-1,1,2,2-d4
2-Mercaptoethyl alcohol
2-mercaptoethynol
2-Sulfanylethan-1-ol
2-sulfanylethynol
2-Thioethanol
2-巯基乙醇 [Chinese]
Cuprate(6-), μ-2,2-(1-methyl-1,2-ethanediyl)bisimino(6-fluoro-1,3,5-triazine-4,2-diyl)imino(2-hyd
DTT
DTV
Ethylene glycol, monothio-
ETHYLTHIO, 2-HYDROXY-
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41218
Hydroxyethyl mercaptan
hydroxyethyl sulfide
Mercaptoetanol
Monothioglycol
SH2Q [WLN]
ß-mercaptoethanol
Thioethylene glycol, Thioglycol
Thioglycol
Thiomonoglycol
WLN: SH2Q
β Mercaptoethanol
β-Hydroxyethanethiol
β-Hydroxyethylmercaptan
β-mercaptoethanol
β-Mercaptoethanol, Molecular Biology Grade – CAS 60-24-2 –
Other names: β-Hydroxyethanethiol; β-Hydroxyethylmercaptan; β-Mercaptoethanol; Ethylene glycol, monothio-; Monothioethylene glycol; Monothioglycol; Thioethylene glycol; Thioglycol; Thiomonoglycol; 1-Ethanol-2-thiol; 1-Hydroxy-2-mercaptoethane; 1-Mercapto-2-hydroxyethane; 2-Hydroxy-1-ethanethiol; 2-Hydroxyethanethiol; 2-Hydroxyethyl mercaptan; 2-Mercapto-1-ethanol; 2-Mercaptoethanol; 2-Mercaptoethyl alcohol; 2-ME; Hydroxyethyl mercaptan; Mercaptoethanol; USAF EK-4196; 2-Thioethanol; Emery 5791; UN 2966; NSC 3723; 2-Sulfanylethanol; 2-Sulfanylethan-1-ol
Reducing agent – 2-Mercaptoethanol
The addition of a reducing agent to an assay may be important to prevent the oxidation of cysteines in the proteins being studied and thus the formation of disulfides. The most commonly used reducing agents are dithiothreitol (DTT), β-mercaptoethanol (β-ME) and tris(2-carboxyethyl)phosphine (TCEP).
2-mercaptoethanol or β-mercaptoethanol or BME is a chemical compound of the formula HOCH2CH2SH, a “hybrid” of ethylene glycol and ethanedithiol. At room temperature it is a liquid with a foul-smelling odor. The presence of the thiol -SH function makes 2-mercaptoethanol a reducing agent widely used in biochemistry to protect proteins against oxidation.
The denaturation of proteins requires the reduction of disulfide bridges, which are crucial for the tertiary or quaternary structure of certain proteins. It is commonly used to reduce disulfide bridges present in proteins and can play a role as a biological antioxidant. It is also used because of its hydroxyl group, which makes it miscible in water and reduces the volatility (and therefore the odor) of thiol.
2-Mercaptoethanol is a powerful reducing agent used in cell culture media to prevent toxic levels of oxygen radicals.
GENERAL DESCRIPTION OF ORGANOSULFUR COMPOUNDS
Mercaptan: any of a class of organosulfur compounds is similar to the alcohol and phenol but containing a sulfur atom in place of the oxygen atom. Compounds containing -SH as the principal group directly attached to carbon are named ‘thiols’. In substitutive nomenclature their names are formed by adding ‘-thiol’ as a suffix to the name of the parent compound. When -SH is not the principal group, the prefix ‘mercapto-‘ is placed before the name of the parent compound to denote an unsubstituted -SH group. ‘thio’ is a chemical prefix indicates the replacement of an oxygen in an acid radical by sulfur with a negative valence of 2. Sulfur analog of alcohol is called thiol (or mercaptan), and ether analog is called sulfide.
Sulfate (also spelled sulphates in Euorpe) is any chemical compound related to sulfuric acid, formed by replacing one or both of the hydrogens with a metal or a radical. Sulfite is any salt of sulfurous acid, chemical species H2SO3, which is formed in aqueous solutions of sulfur dioxide. Sulfurous acid is a clear liquid with a strong sulfur aroma. Sulfide is a compound having one or more sulfur atoms in which the sulfur is connected directly to a carbon, metal, or other nonoxygen atom; for example, sodium sulfide, Na2S. Sulfur compounds are used in the synthesis of medicine and chemicals, manufacture of wood, pulp and paper. They are used in winemaking, brewing, food preservation, metallurgy, engraving process, ore flotation, additive in making steel, bleaching, metal treatment and as an analytic reagent.
The first chemical contrast of thiols and sulfides with alcohols and ethers is acidity which is important in organic reactions. Thiols are stronger acids than relevant alcohols and phenols.Thiolate conjugate bases are easily formed, and are excellent nucleophiles in SN2 reactions of alkyl halides and tosylates. The nucleophilicity of sulfur is much greater than that of oxygen, resulting in a number of useful electrophilic substitution reaction that are rare by oxygen. For example, sulfides form (with alkyl halides) ternary sulfonium salts, in the same alkylattion of tert-amines quaternary ammonium salts, whereas ternary oxonium salts are prepared only under extream conditions. Without exception, sulfoxides, sulfinate salts and sulfite anion also alkylate on sulfur, despite of the partial negative formal charge on oxygen and partial positive charge on sulfur. The second character is the oxidation states of sulfur. Oxygen has only two oxidation states, whereas sulfur covers from –2 to +6 as follows:
-2: Hydrogen Sulfide (H2S), sulfides, sulfonium ions
-1: disulfides
0: S elemental, sulfoxides, sulfenic acids
+2: sulfones, sulfinic acids
+4: sulfonic acids, sulfite esters
+6: sulfate esters
One more sulfur compound’s contrast with oxygen analog is in oxidation chemistry. Oxidation of sulfur compounds changes the oxidation state of sulfur rather than carbon, whereas, oxidation of alcohols to aldehydes and ketones changes the oxidation state of carbon not oxygen. Thiols is oxidized to S-S single bond (disufide) which is stronger than O–O bond in peroxide. Disufide forms sulfenyl chlorides (with chlorine in mild condition) or sulfonic acids under harder condition. Oxidation of sulfides with hydrogen peroxide (or peracids) yields sulfoxides and then to sulfones. A certain sulfoxide compound such as dimethyl sulfoxide can be used as an effective oxygen source in the oxidation reaction of primary and secondary alcohols to aldehydes and ketones. DMSO easily is reduced to dimethyl sulfide and water is taken up by the electrophile. oxidation procedure is very mild and tolerates a variety of other functional groups, including those having oxidizable nitrogen and sulfur atoms.
Organosulfur compounds are widely used in refineries, steamcrackers, aromatic extraction and petrochemical manufacturing as they acts as hydrotreating catalysts, initial catalyst improvers, sulfur source and catalyst presulfiding. Sulfoxide (R2SO) is any of various organic sulfur compounds having the group -SO (sulfinyl group) whereas sulfone (RSOOR) with the group -SO2 (sulfonyl group). They are derived from oxidation of sulfides. They are widely used as solvent of both extraction and reaction as well as intermediates for the synthesis of textile chemicals and pharmaceuticals and agrochemicals. Dimethyl Sulfoxide is used as an effective extraction solvent and solvent improver for the separation of aromatic compounds (benzene, toluene and xylenes) from aliphatic hydrocarbons, and for fractionation of unsaturated components (olefins and alkynes) from saturated feedstock. It is used as a thermally stable medium for carrying out chemical reactions to make pharmaceuticals, agrochemicals (especially pyrethroid insecticides) paint and coating materials and biocides. Its pharmaceutical grade can be used as a as a local analgesic and anti-inflammatory agent. Sulfolane is used as a extraction as well as a reaction solvent. It is used to separate aromatic hydrocarbons (benzene, toluene and xylenes), It is used to separate n-propyl alcohol and sec-butyl alcohol. It is used to purify natural gas streams and for fractionation of fatty acids into saturated and unsaturated components. It is used as a reaction solvent for the preparation of aromatic sulfonic acids, pyridines, isocyanates and pharmaceuticals. It can also be involved in the halogen exchange process and polymerization process. It is used as a plasticizer and curing agent.
Organosulfur compounds have diverse applications in the organic synthesis as organosulfur sources into target organic molecules in the manufacture of pharmaceuticals, adhesives, biocides, agrochemical products, lubricant and fuel additives for high pressure, surfactants, water treatment chemicals, dyes, flavors & fragrances, and photographic chemicals.
Sulfonamide is an organic sulfur compounds containing the radical -SO2NH2 (the amides of sulfonic acids). Its molecular structure is similar to p-Aminobenzoic acid (PABA) which is needed in bacteria organisms as a substrate of the enzyme dihydropteroate synthetase for the synthesis of tetrahydrofolic acid (THF). Sulfonamides, derived from chiefly sulfanilamide, are capable of interfering with the metabolic processes in bacteria that require PABA. They act as antimicrobial agents by inhibiting bacterial growth and activity and called sulfa drugs. They are used in the prevention and treatment of bacterial infections, diabetes mellitus, edema, hypertension, and gout.
Thiophene, also known as Thiofuran, is a cyclic compound containing four carbon atoms and one sulphur atom in a ring. It is a toxic, flammable, highly reactive, colorless liquid insoluble in water (soluble in alcohol and ether) and melts at 38 C, boils at 84 C. It is used as a solvent and chemical intermediate. Its derivatives are widely used in manufacturing dyes, aroma compounds and pharmaceuticals. They are used as monomers to make condensation copolymers.
Thiosulfate is a salt containing the negative ion S2O32-, a analog of the sulfate ion (SO42-) where one of the oxygen (O) atoms has been replaced by a sulfur atom. The sulfur atoms of the thiosulfate ion are not equivalent. Thiosulfate is tetrahedral, and the central sulfur is in the formal oxidation state 6+; and the terminal sulfur is in the formal oxidation state 2-. This species is an important reducing agent. Ammonium Thiosulphate is used as the most common component of photographic fixing agent especially for rapid development. It is used as a nitrogen and sulphur fertilizer. It is used to enhance N utilization efficiency of fertilizers such as urea ammonium nitrate. Sodium Thiosulfate is a white translucent crystals or powder that is common as the pentahydrate form; melting at 48 C; readily soluble in water and oil of turpentine; aqueous solution is slightly alkaline which decompose to sulfate and sulfide in the air. It is a moderate reducing agent. Its major use is as a fixing agent in photography for developing film and the extracting silver from ore. It is used in chrome-tanning leather and in chemical manufacture as a source of sulfide ion. It is also used in paper, textile, water treatment industry and gas purification.
Thiocyanate is a salt or ester of thiocyanic acid (HSCN). Aqueous solutions of thiocyanic acid , also called sulfocyanic acid, are very strong acids of the equilibrium mixture of thiocyanic and isothiocyanic. Thiocyanates are bonded through the sulfur(s) with the structure R-S-C≡N or the isomeric R-N=C=S (isothiocyanates). Thiocyanates are bonded through the sulfur(s) which replace for the oxygen (O) atom. Thiocyanates are the sulfur analog of isocyanates. Organic as well as metallic thiocyanates [CuSCN, Ca(SCN)2, NaSCN, KSCN] are very versatile compounds. They have wide range of applications including manufacturing industrial chemicals, pharmaceuticals and pesticides. It is used in freezing solutions, fabric dyeing, electroplating, steel pickling, printing, and corrosion inhibitor against acid gases. It is used in photography industry as a stabilizer or accelerator.
Thiourea (also called Thiocarbamide or Sulfourea) is the diamide of thiocarbonic acid that resembles urea but contains sulfur instead of oxygen. In fct, thiourea occurs as the mixture of two tautomers: S=C(NH2)2 ( Thiourea) + HS=CNHNH2 (Isothiourea), accordingly, provides three functional groups (mino, imino, and thiol). Thiourea is a lustrous white crystalline compound; estimated melting point is 170-180 C; soluble in water and in polar organic solvents; insoluble in non-polar solvents. The exact melting point and boiling point are not available since rearrangement to ammonium thiocyanate (NH4SCN) occurs at about 135 C and decomposition occurs. It can be prepared by heating ammonium thiocyanate, or by the addition of hydrogen sulfide to cyanamide. The latter is the more common method. Thiourea is used directly in ore filtering, metal refinery and cleaning, isomerization catalyst (conversion of maleic to fumaric acid) and as an additive in fertilizers (to inhibit the nitrification process), drilling auxiliaries, light-sensitive photocopy paper and explosives. It is used as a fixing agent in photography, as a liquefying agent in animal hide glue, as an insecticide, as a textile-treating agent, and as an intermediate to produce other compounds. Thiourea and its derivatives are versatile intermediates for the synthesis of modified thermosetting resins, thiourea dioxide, dyes, flame retardants, vulcanization accelerators, plant protection agents, pesticides, amino resins, peptizing agents, fungicides, hair preparations, dry cleaning chemicals, corrosion inhibitors and thiazole drugs (e.g., antiseptic, thyrotherapeutic, narcotic, and tuberculostatic agents). Dithiobiurea possesses a wide dipole moment and thus is involved in the forming wide metal chelated complexes as the radioactiv-compound which used in radiopharmaceutical imaging, inhibiting enzyme function, kidney function study and to treat toxic metal poisoning. It is used in co-crystals development used in the field of nonlinear optics to generate new coherent wavelengths.
Thioglycolic acid, a simple sulfur group- chained carboxylic acid, is a clear liquid; melts at -16. c, boils at 96 C; soluble in water. It is an useful chemical intermediate in the chemical reactions such as addition, elimination and cyclization. Sulfur group will react with bases, acids, ketones and organic halogen compounds, whereas the carboxylic group will preferentially react In the presence of alcohols or amines. The applications of thioglycolic acid and its derivatives are wide in the fields of of PVC stabilizers, down-hole acidizing, corrosion inhibition in the oil field industry, manufacturing of pharmaceuticals, agrochemicals and dyes, hair care products (waving, hair removal and hair straightening), shrink-resistant treatment of wool, fabric dying, leather processing.
Isethionic acid, short chain alkan sulfonate containing hydroxy group, is a water soluble liquid used in the manufacture of mild, biodegradable and high foaming anionic surfactants which provides gentle cleansing and soft skin feel.
Biochemical properties
Proteins are denatured by 2-mercaptoethanol via its ability to cleave disulfide bonds:
cysS-Scys + 2 HOCH2CH2SH → 2 cysSH + HOCH2CH2S-SCH2CH2OH
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
β-Mercaptoethanol; 2-Hydroxyethylmercaptan; BME; Thioethylene glycol; 2-Hydroxy-1-ethanethiol; Monothioethyleneglycol
CAS NUMBER: 60-24-2
2-Mercaptoethanol
Application Notes
2-Merceptoethanol is suitable for reducing protein disulfide bonds prior to polyacrylamide gel electrophoresis and is usually included in a sample buffer for SDS-PAGE. 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 or β-mercaptoethanol or BME is a chemical compound of the formula HOCH2CH2SH, a “hybrid” of ethylene glycol and ethanedithiol. At room temperature it is a liquid with a foul-smelling odor. The presence of the thiol -SH function makes 2-mercaptoethanol a reducing agent widely used in biochemistry to protect proteins against oxidation.
The denaturation of proteins requires the reduction of disulfide bridges, which are crucial for the tertiary or quaternary structure of certain proteins. It is commonly used to reduce disulfide bridges present in proteins and can play a role as a biological antioxidant. It is also used because of its hydroxyl group, which makes it miscible in water and reduces the volatility (and therefore the odor) of thiol.
2-Mercaptoethanol is a powerful reducing agent used in cell culture media to prevent toxic levels of oxygen radicals.
Chain Transfer Agents
Product overview
Mercaptans are commonly used as reactants in the manufacturing processes of many common rubber and thermoplastic materials.
The use of mercaptans allows for fine control of the molecular chain length during polymerization, leading to easy processing conditions and mechanical performance of the resulting polymer.