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COO/COA

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108995

Methyl thioglycolate

Name: Methyl thioglycolate
Brand: ALDRICH

95%

Synonym(s):

Methyl mercaptoacetate

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About This Item

Linear Formula:

HSCH₂CO₂CH₃

CAS Number:

2365-48-2

Molecular Weight:

106.14

Beilstein:

506259

EC Number:

219-121-7

MDL number:

MFCD00004873

UNSPSC Code:

12352100

PubChem Substance ID:

24846848

NACRES:

NA.22

Assay

95%

reaction suitability

reagent type: ligand
reaction type: [1,2]-Wittig Rearrangement

refractive index

n20/D 1.466 (lit.)

bp

42-43 °C/10 mmHg (lit.)

density

1.187 g/mL at 25 °C (lit.)

functional group

ester
thiol

SMILES string

COC(=O)CS

InChI

1S/C3H6O2S/c1-5-3(4)2-6/h6H,2H2,1H3

InChI key

MKIJJIMOAABWGF-UHFFFAOYSA-N

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General description

Methyl thioglycolate reacts with nonprotein component of the antitumor antibiotic neocarzinostatin to form 1:1 adduct. It reacts with isothiocyanate to form Rhodanine.

Application

Methyl thioglycolate was used in the preparation of:

3-carbomethoxy-4- oxotetrahydrothiopyran, 2- and 4-carbomethoxy-3-oxotetrahydrothiophene
methyl thioglycolate and aminoethanethiol conjugated gold nanorods.

Thiol Organocatalyst used in conjunction with visible light photocatalysis to affect the direct arylation of benzylic ether C-H bonds

A General Strategy for Organocatalytic Activation of C–H Bonds via Photoredox Catalysis: Direct Arylation of Benzylic Ethers

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Pictograms

GHS02,GHS06

Signal Word

Danger

Hazard Statements

H226,H301,H315,H319,H332,H335

Precautionary Statements

P210 - P233 - P301 + P310 - P303 + P361 + P353 - P304 + P340 + P312 - P305 + P351 + P338

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Inhalation - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

132.8 °F - closed cup

Flash Point(C)

56 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Sigma-Aldrich

556912

Isooctyl 3-mercaptopropionate

Sequence preference for strand cleavage of gapped duplexes by dynemicin A: possible mechanism of sequence-dependent double-stranded breaks.

T Kusakabe et al.

Biochemistry, 34(31), 9944-9950 (1995-08-08)

A double-stranded DNA cleavage mechanism by a novel enediyne type antitumor antibiotic, dynemicin A, has been investigated through sequence-dependent strand breakage of a series of duplexes containing a single nucleotide gap. We found that (1) dynemicin A breaks specifically at

Thiol addition to quinones: model reactions for the inactivation of thymidylate synthase by 5-p-benzoquinonyl-2'-deoxyuridine 5'-phosphate.

M K Vadnere et al.

Journal of medicinal chemistry, 29(9), 1714-1720 (1986-09-01)

The reaction of methyl mercaptoacetate (5) with phenyl-p-benzoquinone (6) or 5-p-benzoquinonyl-3',5'-di-O-acetyl-2'-deoxyuridine (10) resulted in the formation of the three possible adducts to the quinone rings of 6 and 10; an additional product in the reaction with 10 was the unsubstituted

Supercoiling affects the accessibility of glutathione to DNA-bound molecules: positive supercoiling inhibits calicheamicin-induced DNA damage.

W A LaMarr et al.

Proceedings of the National Academy of Sciences of the United States of America, 95(1), 102-107 (1998-02-21)

DNA superhelical tension, an important feature of genomic organization, is known to affect the interactions of intercalating molecules with DNA. However, the effect of torsional tension on nonintercalative DNA-binding chemicals has received less attention. We demonstrate here that the enediyne

Optimization of efficiency in the glyoxalase pathway.

D J Creighton et al.

Biochemistry, 27(19), 7376-7384 (1988-09-20)

A quantitative kinetic model for the glutathione-dependent conversion of methylglyoxal to D-lactate in mammalian erythrocytes has been formulated, on the basis of the measured or calculated rate and equilibrium constants associated with (a) the hydration of methylglyoxal, (b) the specific

Reductive and nucleophilic activation products of dynemicin A with methyl thioglycolate. A rational mechanism for DNA cleavage of the thiol-activated dynemicin A.

Y Sugiura et al.

Biochemistry, 30(12), 2989-2992 (1991-03-26)

The reaction products of methyl thioglycolate with dynemicin A, dynemicin H and dynemicin S, were isolated by HPLC purification and identified spectroscopically. The major product, dynemicin H (C30H23NO9), was determined to be a C-8 hydrogen analogue of dynemicins L and

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