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170216

Sigma-Aldrich

Methylglyoxal 1,1-dimethyl acetal

≥97%

Synonym(s):

1,1-Dimethoxyacetone, Pyruvaldehyde-1-dimethyl acetal, Pyruvic aldehyde dimethyl acetal

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About This Item

Linear Formula:
CH3COCH(OCH3)2
CAS Number:
6342-56-9
Molecular Weight:
118.13
Beilstein:
1560557
EC Number:
228-735-4
MDL number:
MFCD00008758
UNSPSC Code:
12352100
PubChem Substance ID:
24850288
NACRES:
NA.22

Quality Level

200

Assay

≥97%

form

liquid

refractive index

n20/D 1.398 (lit.)

bp

143-147 °C (lit.)

density

0.976 g/mL at 25 °C (lit.)

functional group

acetal
ether
ketone

SMILES string

COC(OC)C(C)=O

InChI

1S/C5H10O3/c1-4(6)5(7-2)8-3/h5H,1-3H3

InChI key

ULVSHNOGEVXRDR-UHFFFAOYSA-N

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Application

Methylglyoxal 1,1-dimethyl acetal was used in the synthesis of methylglyoxal via hydrolysis in the presence of H2SO4. It was used to investigate the effects of methylglyoxal-mediated glycation on the structure, thermal stability and enzyme activity of yeast enolase in vivo.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

78.8 °F - closed cup

Flash Point(C)

26 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG9995
BCCG0187
BCCD7691
BCBX4201
BCBW3279

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Svetlana I Dorovskikh et al.
Biomedicines, 9(8) (2021-08-28)
This work is aimed at developing the modification of the surface of medical implants with film materials based on noble metals in order to improve their biological characteristics. Gas-phase transportation methods were proposed to obtain such materials. To determine the
Ajit Ghosh et al.
Scientific reports, 6, 18358-18358 (2016-01-07)
Glyoxalase pathway, comprising glyoxalase I (GLY I) and glyoxalase II (GLY II) enzymes, is the major pathway for detoxification of methylglyoxal (MG) into D-lactate involving reduced glutathione (GSH). However, in bacteria, glyoxalase III (GLY III) with DJ-1/PfpI domain(s) can do
K Ispolnov et al.
Journal of applied microbiology, 104(4), 1092-1102 (2008-01-16)
The purpose of this study was to investigate the behaviour of Saccharomyces cerevisiae in response to extracellular methylglyoxal. Cell survival to methylglyoxal and the importance of phosphates was investigated. The role of methylglyoxal detoxification systems and methylglyoxal-derived protein glycation were
Ricardo A Gomes et al.
The FEBS journal, 272(17), 4521-4531 (2005-09-01)
Methylglyoxal is the most important intracellular glycation agent, formed nonenzymatically from triose phosphates during glycolysis in eukaryotic cells. Methylglyoxal-derived advanced glycation end-products are involved in neurodegenerative disorders (Alzheimer's, Parkinson's and familial amyloidotic polyneurophathy) and in the clinical complications of diabetes.
Giulia Milordini et al.
Frontiers in molecular biosciences, 7, 104-104 (2020-06-26)
Epidemiological evidence shows an increased risk for developing Alzheimer's disease in people affected by diabetes, a pathology associated with increased hyperglycemia. A potential factor that could explain this link could be the role that sugars may play in both diseases
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