Chemical Properties Description Sources References
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Methylglyoxal

Chemical Properties Description Sources References
Product Name
Methylglyoxal
CAS No.
78-98-8
Chemical Name
Methylglyoxal
Synonyms
2-oxopropanal;PYRUVALDEHYDE;PYRUVIC ALDEHYDE;Propanedione;1,2-Propanedione;methylglyoxal solution;CH3COCHO;1-Ketopropionaldehyde;Pyruvaldehyde, 40% in water;yoxaL
CBNumber
CB1157969
Molecular Formula
C3H4O2
Formula Weight
72.06
MOL File
78-98-8.mol
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Methylglyoxal Property

Melting point:
25 °C
Boiling point:
72 °C
Density 
1.19 g/mL at 20 °C
vapor pressure 
25.09hPa at 20℃
refractive index 
n20/D 1.4209
RTECS 
UZ0700000
FEMA 
2969 | PYRUVALDEHYDE
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Methanol (Slightly), Water (Soluble)
form 
Solution
color 
Clear yellow to yellow-brown
Odor
at 1.00 % in propylene glycol. sweet acidic ethereal brown rum
Odor Type
caramellic
Water Solubility 
>=10 g/100 mL at 17 ºC
Sensitive 
Air Sensitive
JECFA Number
937
Merck 
14,6081
BRN 
906750
InChIKey
AIJULSRZWUXGPQ-UHFFFAOYSA-N
LogP
-1.06 at 25℃
CAS DataBase Reference
78-98-8(CAS DataBase Reference)
IARC
3 (Vol. 51) 1991
NIST Chemistry Reference
Propanal, 2-oxo-(78-98-8)
EPA Substance Registry System
Methylglyoxal (78-98-8)
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Safety

Hazard Codes 
Xn,Xi,C
Risk Statements 
22-36-35
Safety Statements 
26-36-45-36/37/39
RIDADR 
UN 3265 8 / PGIII
WGK Germany 
-
Hazard Note 
Irritant
TSCA 
Yes
HS Code 
29121900
Hazardous Substances Data
78-98-8(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H290May be corrosive to metals

H317May cause an allergic skin reaction

H318Causes serious eye damage

H341Suspected of causing genetic defects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P234Keep only in original container.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
67028
Product name
Methylglyoxal solution
Purity
technical, ~40% in H2O
Packaging
100ml
Price
$376
Updated
2024/03/01
Sigma-Aldrich
Product number
67028
Product name
Methylglyoxal solution
Purity
technical, ~40% in H2O
Packaging
500ml
Price
$1210
Updated
2023/06/20
Alfa Aesar
Product number
B24664
Product name
Pyruvic aldehyde, 35-45% w/w aq. soln
Packaging
25g
Price
$30.1
Updated
2024/03/01
Alfa Aesar
Product number
B24664
Product name
Pyruvic aldehyde, 35-45% w/w aq. soln
Packaging
100g
Price
$70.1
Updated
2024/03/01
Sigma-Aldrich
Product number
W296902
Product name
Pyruvaldehyde solution
Purity
40 wt. % in H2O
Packaging
sample
Price
$55.4
Updated
2024/03/01
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Methylglyoxal Chemical Properties,Usage,Production

Chemical Properties

Methylglyoxal (MG, C3H4O2) is also known as 2-oxopropanal, pyruvaldehyde, pyruvic aldehyde, 2-ketopropionaldehyde, acetylformaldehyde, propanedione, or propionaldehyde, which is a clear yellow slightly viscous liquid with a pungent odor which polymerizes readily and forms a variety of cyclic and acyclic structures. It is faintly acidic to litmus. The solubility of methylglyoxal is more than 10 g/100 mL water at 17°C. In water, MG is present mostly in the mono and dihydrate forms, while non hydrated MG is only present in traces.

Description

Methylglyoxal is an organic compound formed as a side-product of several metabolic pathways. It has been proved to be an intermediate in the metabolism of acetone and its derivatives. It is produced to insure every cell's health, which is used commonly as a reagent in organic synthesis, as a flavoring agent, and in tanning. However, the most important application is in pharmaceuticals. Methylglyoxal is found in all honeys, especially in manuka honey, in which it has strong antibacterial and antiviral property. Methylglyoxal is transferred into the honey where it remains stable. Dietary Methylglyoxal found in Manuka Honey is resistant to heat, light, body fluids and enzymatic activity. This property makes MGO Manuka Honey superior to any other honey. Its anti-cancer potential has been already demonstrated in human body and it has proved to be effective to eradicate most cancer types.

Sources

Many food products, beverages, water, rain, clouds, fog water, and urban atmosphere as well as cigarette smoke represent exogenous sources of methylglyoxal. The origins of MG in food and beverages are sugars, the products of the Maillard reaction, lipids and microorganisms formed during industrial processing, cooking, and prolonged storage. In vivo Methylglyoxal can be formed in many enzymatic and nonenzymatic pathways. Enzymatic pathways include reactions catalyzed by triosephosphate isomerase, cytochrome P450 2E1, myeloperoxidase, and aminooxidase, whereas nonenzymatic pathways include decomposition of dihydroxyacetone phosphate (DAP), the Maillard reaction, oxidation of acetol, and lipid peroxidation.

References

https://en.wikipedia.org/wiki/Methylglyoxal
https://pubchem.ncbi.nlm.nih.gov/compound/880#section=Top
http://www.cancertreatmentsresearch.com/methilglyoxal/

Description

Methylglyoxal (MG) is a highly reactive a-dicarbonyl compound that is primarily generated endogenously during glycolytic pathways (glucose and fructose metabolism) in cells and exogenously due to autoxidation of sugar, degradation of lipids, and fermentation during food and drink processing. Methylglyoxal polymerizes readily; it is hygroscopic and incompatible with strong oxidizing agents and bases. Methylglyoxal may be present as a free molecule in the diet or bound to biological materials, such as proteins, and as advanced glycation end products (AGEs), which are poorly absorbed. Methylglyoxal has been indicated in pathological events associated with hyperglycemia in both type 1 and type 2 diabetes and in other diabetic complications as either a direct toxin or as a precursor for AGEs. In animal studies, MG has been shown to induce tumorigenesis, but has also been reported as a tumoristatic agent. Methylglyoxal has been identified as the dominant antibacterial constituent of manuka honey.

Chemical Properties

clear yellow to yellow-brown solution

Chemical Properties

Pyruvaldehyde has a characteristic, pungent, stinging odor with a pungent, caramellic, sweet flavor.

Occurrence

Reported found in the dry distillate of Manilla copal. Also reported found in apple juice, orange juice, celery root, rutabaga, tomato, wheaten bread, white bread, roasted and raw turkey, cognac, roasted barley, beer, cocoa, coffee and roasted pecans.

Uses

Organic synthesis, as of complex chemical com- pounds such as pyrethrins, tanning leather, flavor- ing.

Uses

Used in organic synthesis, as a flavoring agent, and in tanning leather. Commercial formulation is available as a 30% aqueous solution. No safety concern at current levels of intake when used as a flavoring agent.

Uses

Methylglyoxal solution has been used:

  • to assess glyoxalase 1 (GLO1) enzymatic activity
  • as an advanced glycation end (AGE) forming agent for the preparation of albumin in vitro
  • to regulate anxiety like behavior in mice
  • to induce peritoneal fibrosis in rats
  • to study the chromatographic retention characteristics of organic chemicals and metal DNA adducts
  • for intraplantar injection in mice to investigate peripheral and central components of methylglyoxal (MG)-transient receptor potential ankyrin 1 (TRPA1)-adenylyl cyclase 1 isoform (AC1) pathway

Preparation

By distilling a dilute solution of dihydroxyacetone from calcium carbonate; by oxidation of acetone with selenium dioxide; by heating dihydroxy acetone with phosphorus pentoxide; by warming isonitroso acetone with diluted H2SO4.

Definition

ChEBI: A 2-oxo aldehyde derived from propanal.

Taste threshold values

Taste characteristics at 0.1%: sweet, caramellic with a dairy creamy nuance

General Description

Clear yellow slightly viscous liquid with a pungent odor. Yellowish-green vapors. Faintly acidic to litmus.

Air & Water Reactions

Water soluble.

Reactivity Profile

Methylglyoxal polymerizes readily. Methylglyoxal is hygroscopic. Methylglyoxal is incompatible with strong oxidizing agents and bases. Methylglyoxal is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Fire Hazard

Literature sources indicate that Methylglyoxal is nonflammable.

Flammability and Explosibility

Non flammable

Environmental Fate

Methylglyoxal production and use as a chemical intermediate and flavoring agent may result in its release to the environment through various waste streams. If released into water, MG is not expected to adsorb to suspended solids and sediment based on the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon the estimated Henry’s Law constant. If released to soil, MG is expected to have very high mobility based upon an estimated Koc of 1 determined from the structure estimation method. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions.
Methylglyoxal serves as a substrate for the isozymes E1, E2, and E3 of human aldehyde dehydrogenase. Oxidation of MG by these isozymes generated pyruvate. Methylglyoxal is a partially oxidized compound obtained from the tropospheric oxidation of numerous hydrocarbons, of both biogenic and anthropogenic origin. If released to the air, an estimated vapor pressure of 27 mm Hg at 25 ℃ indicates MG will exist solely as a vapor in the atmosphere. Vapor-phase MG 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 30 h. Methylglyoxal absorbs light at wavelengths >290 nm and, therefore, is susceptible to direct photolysis by sunlight; half-lives of 2–4 h have been reported.

Purification Methods

Commercial 30% (w/v) aqueous solution is diluted to about 10% and distilled twice, taking the fraction boiling below 50o/20mm Hg. (This treatment does not remove lactic acid). [Beilstein 1 IV 3631.]

Toxicity evaluation

Endogenously formed MG modifies arginine and lysine residues in proteins that form AGEs, which have been associated with diabetic complications and some neurodegenerative diseases. In different cell lines, MG treatment has been shown to induce apoptosis as measured by nuclear fragmentation and apoptotic body formation, indicating an increase in apoptosis. At the mitochondrial level, exogenous MG is highly toxic as it promotes proliferation, swelling, and membrane derangement. In both in vitro and in vivo studies, MG treatment has been shown to significantly reduce antioxidant enzymes and elevate reactive oxygen species that lead to oxidative stress-mediated cell death. Genotoxicity has been observed in both in vivo and in vitro studies, as MG is capable of binding to cellular macromolecules and forming DNA adducts.

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Methylglyoxal Suppliers

Shanghai YouPeng Chemical Co. Ltd.
Tel
021-69005955 13701776567
Fax
021-69005775
Email
youpengchem@163.com
Country
China
ProdList
4304
Advantage
56
Cangzhou Fengmao Biotech Co., Ltd.
Tel
0317-5304268 13582748294
Fax
+86-317-5304268
Email
info@goldlionchem.com
Country
China
ProdList
112
Advantage
60
Weifang Qianyuan Biotechnology Co., Ltd.
Tel
18678041314 18765609661
Email
2547772582@qq.com
Country
China
ProdList
505
Advantage
58
Nanjing Jiaju Pharmaceutical Technology Co., Ltd.
Tel
13022518189
Email
321278398@qq.com
Country
China
ProdList
130
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15848
Advantage
69
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30132
Advantage
84
ShangHai DEMO Chemical Co.,Ltd
Tel
400-021-7337 2355568890
Fax
0086-21-50182339
Email
sales@demochem.com
Country
China
ProdList
2572
Advantage
57
BeiJing Hwrk Chemicals Limted
Tel
0757-86329057 18501085097
Fax
010-89508210
Email
sales3.gd@hwrkchemical.com
Country
China
ProdList
7508
Advantage
55
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View Lastest Price from Methylglyoxal manufacturers

Hebei Duling International Trade Co. LTD
Product
Methylglyoxal 78-98-8
Price
US $20.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000 tons
Release date
2023-01-16
Hebei Yanxi Chemical Co., Ltd.
Product
methylglyoxal 78-98-8
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20tons
Release date
2023-09-15
Hebei Guanlang Biotechnology Co., Ltd.
Product
Methylglyoxal 78-98-8
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2023-02-25

78-98-8, MethylglyoxalRelated Search:


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