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M6250

Sigma-Aldrich

2-Mercaptoethanol

≥99.0%

Synonym(s):

β-Mercaptoethanol, 2-Hydroxyethylmercaptan, BME, Thioethylene glycol

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About This Item

Linear Formula:
HSCH2CH2OH
CAS Number:
60-24-2
Molecular Weight:
78.13
Beilstein:
773648
EC Number:
200-464-6
MDL number:
MFCD00004890
UNSPSC Code:
12352100
PubChem Substance ID:
57654402
NACRES:
NA.22

vapor density

2.69 (vs air)

Quality Level

200

vapor pressure

1 mmHg ( 20 °C)

Assay

≥99.0%

form

liquid

expl. lim.

18 %

concentration

14.3 M (pure liquid)

refractive index

n20/D 1.500 (lit.)

pH

4.5-6 (20 °C, 500 g/L)

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

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General description

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

Application

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

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 2 - Eye Dam. 1 - Repr. 2 - Skin Irrit. 2 - Skin Sens. 1A - STOT RE 2 Oral

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

165.2 °F - closed cup

Flash Point(C)

74 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Silver stain for proteins in polyacrylamide gels: a modified procedure with enhanced uniform sensitivity.
Morrissey JH.
Analytical Biochemistry, 117(2), 307-310 (1981)
Establishment of 2-mercaptoethanol-dependent differentiated insulin-secreting cell lines.
Asfari M, et al.
Endocrinology, 130(1), 167-178 (1992)
Manching Ku et al.
PLoS genetics, 4(10), e1000242-e1000242 (2008-11-01)
In embryonic stem (ES) cells, bivalent chromatin domains with overlapping repressive (H3 lysine 27 tri-methylation) and activating (H3 lysine 4 tri-methylation) histone modifications mark the promoters of more than 2,000 genes. To gain insight into the structure and function of
Katharina Rothe et al.
Blood, 123(23), 3622-3634 (2014-04-24)
Previous studies demonstrated that imatinib mesylate (IM) induces autophagy in chronic myeloid leukemia (CML) and that this process is critical to cell survival upon therapy. However, it is not known if the autophagic process differs at basal levels between CML
E M Michalak et al.
Cell death and differentiation, 15(6), 1019-1029 (2008-02-09)
The ability of p53 to induce apoptosis in cells with damaged DNA is thought to contribute greatly to its tumour suppressor function. P53 has been proposed to induce apoptosis via numerous transcriptional targets or even by direct cytoplasmic action. Two
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Protocols

Protocols for the Fmoc SPPS of Cysteine-containing Peptides

Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.

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