Page last updated: 2024-11-04

pyruvaldehyde

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Pyruvaldehyde: An organic compound used often as a reagent in organic synthesis, as a flavoring agent, and in tanning. It has been demonstrated as an intermediate in the metabolism of acetone and its derivatives in isolated cell preparations, in various culture media, and in vivo in certain animals. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

methylglyoxal : A 2-oxo aldehyde derived from propanal. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID880
CHEMBL ID170721
CHEBI ID17158
MeSH IDM0018286

Synonyms (94)

Synonym
nsc-133493
51252-84-7
nsc133493
nsc133492
nsc-133492
nsc626580
nsc-626580
CHEBI:17158 ,
ch3cocho
2-oxopropionaldehyde
1,2-propanedione
alpha-ketopropionaldehyde
nsc 337790
methyl glyoxal
acetalformaldehyde
nsc 79019
brn 0906750
einecs 201-164-8
nsc 626580
nsc79019
propanal, 2-oxo-
acetylformyl
wln: vhv1
propionaldehyde, 2-oxo-
glyoxal, methyl
1-ketopropionaldehyde
propionaldehyde, 2-keto
nsc-79019
pyroracemic aldehyde
propanedione
.alpha.-ketopropionaldehyde
propanolone
propanal, 2-oxo- (9ci)
fema no. 2969
pyruvaldehyde (8ci)
alpha-ketopropionic aldehyde
2-oxo-propanal
oxopropanal
ccris 1741
78-98-8
C00546
METHYL-GLYOXAL ,
pyruvaldehyde
pyruvic aldehyde
2-ketopropionaldehyde
acetylformaldehyde
methylglyoxal
2-oxopropanal
DB03587
acetyl formaldehyde
194597AC-5BFC-42EA-B6C8-DA2E5FAA13AF
2-oxo-propionaldehyde
CHEMBL170721
AKOS000119318
A839545
2-oxopropanal;2-hydroxyprop-2-enal
unii-722kld7415
ec 201-164-8
722kld7415 ,
4-01-00-03631 (beilstein handbook reference)
hsdb 7510
BP-20618
FT-0646558
AB00820
EPITOPE ID:143620
gtpl6303
methylglyoxal [iarc]
nsc-337790
methylglyoxal [who-dd]
methylglyoxal [mi]
pyruvaldehyde [fhfi]
methyl glyoxal [hsdb]
ethanol ketone
dtxsid0021628 ,
cas-78-98-8
NCGC00356972-01
tox21_303931
dtxcid101628
mfcd00006960
J-510228
F0001-2060
pyruvaldehyde, 40% in water
2-keto propionaldehyde
ketopropionaldehyde
CS-0031856
HY-W020014
2-oxopropanal, 40% in water
Q903881
STR03080
pyruvaldehyde (35per cent w/w aqueous)
pyruvic aldehyde methylglyoxal
EN300-21293
pyruvicaldehyde
Z104495190

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In accordance with previous studies with the rat, p-methoxythiobenzamide was more toxic than thiobenzamide, and conversely p-chlorothiobenzamide was markedly less toxic as assessed by serum alanine aminotransferase (ALT) activity."( Relative hepatotoxicity of 2-(substituted phenyl)thiazoles and substituted thiobenzamides in mice: evidence for the involvement of thiobenzamides as ring cleavage metabolites in the hepatotoxicity of 2-phenylthiazoles.
Mizutani, T; Suzuki, K, 1996
)
0.29
" In this study, the changes in the cellular and extracellular concentrations of these alpha-oxoaldehydes were investigated in murine P388D1 macrophages during necrotic cell death induced by median toxic concentrations of hydrogen peroxide and 1-chloro-2,4-dinitrobenzene (CDNB)."( Accumulation of alpha-oxoaldehydes during oxidative stress: a role in cytotoxicity.
Abordo, EA; Minhas, HS; Thornalley, PJ, 1999
)
0.3
" The results indicate that chronic intake of methylglyoxal, at levels that could be attained in food, is toxic by depletion of blood GSH and could have adverse effect on some GSH dependent functions in vivo."( Toxicity of low levels of methylglyoxal: depletion of blood glutathione and adverse effect on glucose tolerance in mice.
Ankrah, NA; Appiah-Opong, R, 1999
)
0.3
" Glycolaldehyde was more toxic to the SOD-null strain than to its SOD-replete parent, and this differential effect was oxygen-dependent."( The role of alpha,beta -dicarbonyl compounds in the toxicity of short chain sugars.
Fridovich, I; Okado-Matsumoto, A, 2000
)
0.31
" In contrast, most of the recent in vitro studies have assigned a toxic role for methylglyoxal."( In vivo assessment of toxicity and pharmacokinetics of methylglyoxal. Augmentation of the curative effect of methylglyoxal on cancer-bearing mice by ascorbic acid and creatine.
Bhattacharyya, N; Ghosh, M; Ghosh, S; Ray, M; Ray, S; Talukdar, D, 2006
)
0.33
" A transgenic mammalian cell model was developed in which AKR7A2 was overexpressed in V79-4 cells and used to evaluate the ability of AKR7A2 to provide resistance against toxic aldehydes."( Human aldo-keto reductase AKR7A2 protects against the cytotoxicity and mutagenicity of reactive aldehydes and lowers intracellular reactive oxygen species in hamster V79-4 cells.
Ellis, EM; Ferrari, M; Li, D, 2012
)
0.38
"Methylglyoxal is one of the most powerful glycating agents of proteins and other important cellular components and has been shown to be toxic to cultured cells."( A novel mechanism of methylglyoxal cytotoxicity in prostate cancer cells.
Antognelli, C; Fettucciari, K; Mezzasoma, L; Talesa, VN, 2013
)
0.39
" Treatment of MGO for 24 h significantly enhanced 3-h OGD-induced HBMEC toxic effect, which was inhibited by pretreatment of isorhamnetin (100 μmol/L)."( The protective role of isorhamnetin on human brain microvascular endothelial cells from cytotoxicity induced by methylglyoxal and oxygen-glucose deprivation.
Chen, Z; Dai, H; He, P; Li, W; Yan, M, 2016
)
0.43
" For a long time, the reactive α, β-carbonyl ketoaldehyde methylglyoxal (CH3COCHO; MG) has been regarded as merely a toxic metabolite in plants, but, now, emerging as a signal molecule in plants."( Methylglyoxal alleviates cadmium toxicity in wheat (Triticum aestivum L).
Duan, XQ; Li, ZG; Min, X; Wang, Y; Xia, YM; Zhou, ZH, 2017
)
0.46
"Methylglyoxal (MGO) is an endogenous toxic compound that plays a vital role in diabetic complications such as diabetic neuropathy."( The protective effects of moscatilin against methylglyoxal-induced neurotoxicity via the regulation of p38/JNK MAPK pathways in PC12 neuron-like cells.
Lai, MC; Liou, SS; Liu, IM; Liu, WY, 2020
)
0.56
" In the current study, it has been demonstrated that PTS could enhance the level of glyoxalase 1 (GLO-1) and elevate glutathione (GSH) content to active the glyoxalase system, resulting in elimination of the toxic MGO as well as advanced glycation end products (AGEs) in HUVECs."( Pterostilbene prevents methylglyoxal-induced cytotoxicity in endothelial cells by regulating glyoxalase, oxidative stress and apoptosis.
Chen, ZQ; Gu, WT; Nie, H; Tang, D; Wang, SM; Xiao, W; Xu, SH; Xu, YH; Zhang, LY; Zhang, ZT, 2021
)
0.62

Pharmacokinetics

ExcerptReferenceRelevance
" A detailed pharmacokinetic study was done with mouse after oral administration of methylglyoxal."( In vivo assessment of toxicity and pharmacokinetics of methylglyoxal. Augmentation of the curative effect of methylglyoxal on cancer-bearing mice by ascorbic acid and creatine.
Bhattacharyya, N; Ghosh, M; Ghosh, S; Ray, M; Ray, S; Talukdar, D, 2006
)
0.33

Compound-Compound Interactions

ExcerptReferenceRelevance
" In this study, their levels were measured using a sample preparation procedure based on salting-out assisted liquid-liquid extraction (SALLE) and dispersive liquid-liquid microextraction (DLLME) combined with gas chromatography-mass spectrometry (GC-MS)."( Glyoxal and methylglyoxal as urinary markers of diabetes. Determination using a dispersive liquid-liquid microextraction procedure combined with gas chromatography-mass spectrometry.
Campillo, N; Fernández-García, AJ; Hernández-Córdoba, M; Motas, M; Pastor-Belda, M; Pérez-Cárceles, MD; Viñas, P, 2017
)
0.46
" In case of in vivo studies treatment of EAC (Ehrlich Ascites Carcinoma) bearing mice with MG in combination with 5-FU at various doses, demonstrated the same synergistic effect of MG with 5-FU."( Methylglyoxal in combination with 5-Fluorouracil elicits improved chemosensitivity in breast cancer through apoptosis and cell cycle inhibition.
Ghosh, S; Pal, A; Ray, M, 2019
)
0.51

Bioavailability

ExcerptReferenceRelevance
" NO bioavailability was significantly attenuated and accompanied by an increase in superoxide anion immunofluorescence."( Methylglyoxal promotes oxidative stress and endothelial dysfunction.
Crisóstomo, J; Fernandes, R; Matafome, P; Pereira, P; Rodrigues, L; Seiça, RM; Sena, CM, 2012
)
0.38
" The data also indicate that digestion can reduce the bioavailability of the toxic α-dicarbonyl compounds ingested with food."( Effect of in vitro digestion on free α-dicarbonyl compounds in balsamic vinegars.
Gazzani, G; Marrubini, G; Mascherpa, D; Papetti, A, 2013
)
0.39
" As assessed by the ratio of L-arginine/asymmetric dimethylarginine, the bioavailability of nitric oxide was shown to be reduced in hepatic IRI, especially in those patients suffering from perfusion disorders following liver transplantation."( Reactive metabolites and AGE-RAGE-mediated inflammation in patients following liver transplantation.
Brenner, T; Bruckner, T; Fleming, TH; Hofer, S; Martin, EO; Schemmer, P; Spranz, D; Uhle, F; Weigand, MA, 2013
)
0.39
" These findings suggest that α-DC bioavailability could actually depend not on food content but rather on reactions occurring during digestion."( Free α-dicarbonyl compounds in coffee, barley coffee and soy sauce and effects of in vitro digestion.
Gazzani, G; Mascherpa, D; Papetti, A, 2014
)
0.4
" Retrospectively, we studied 37 subjects who had participated in a dietary intervention focused on vitamin D bioavailability from white button mushrooms (WBM)."( A Retrospective Study in Adults with Metabolic Syndrome: Diabetic Risk Factor Response to Daily Consumption of Agaricus bisporus (White Button Mushrooms).
Beelman, RB; Cai, W; Calvo, MS; Goh, BC; Kalaras, MD; Mehrotra, A; Nadkarni, G; Uribarri, J; Wang, L, 2016
)
0.43
" Peritoneal equilibration tests showed that sinefungin attenuated the urea nitrogen transport rate from plasma and the glucose absorption rate from the dialysate."( Inhibition of the H3K4 methyltransferase SET7/9 ameliorates peritoneal fibrosis.
Doi, S; Maeda, K; Masaki, T; Nakashima, A; Sasaki, K; Tamura, R; Ueno, T, 2018
)
0.48
" Extensive clinical trials with derivatisation of available antiglycation agents to increase the bioavailability and decrease side effects are warranted further."( Carbonyl stress in diabetics with acute coronary syndrome.
Bora, S; Shankarrao Adole, P, 2021
)
0.62

Dosage Studied

ExcerptRelevanceReference
" These results collectively suggest that the treatment dosage of MG and glucose could determine the mode of cell death (apoptosis vs."( Methylglyoxal and high glucose co-treatment induces apoptosis or necrosis in human umbilical vein endothelial cells.
Chan, WH; Wu, HJ, 2008
)
0.35
" The results collectively suggest that the treatment dosage of MG and glucose determines the mode of cell death (apoptosis vs."( Impact of methylglyoxal and high glucose co-treatment on human mononuclear cells.
Chan, WH; Hsieh, MS, 2009
)
0.35
"Response surface methodology (RSM) was utilized to investigate the dose-response relationships of a phenolic mixture (catechin, genistein and daidzein) as a pre-thermal processing technique to reduce reactive carbonyl species (RCSs; glyoxal, methylglyoxal and 3-deoxyglucosone) in ultra-high temperature (UHT) bovine milk."( Response surface methodology as optimization strategy for reduction of reactive carbonyl species in foods by means of phenolic chemistry.
Kokkinidou, S; Peterson, DG, 2013
)
0.39
" A cumulative dose-response curve to acetylcholine was obtained to determine endothelium-dependent relaxation."( Methylglyoxal causes endothelial dysfunction: the role of endothelial nitric oxide synthase and AMP-activated protein kinase α.
Ertuna, E; Turkseven, S; Yasa, M; Yetik-Anacak, G, 2014
)
0.4
" And, the dosage used in the above experiments did not affect β-cell viability and apoptosis, although long-term MG induced cell apoptosis and mitochondrial dysfunction."( Effects of phycocyanin on INS-1 pancreatic β-cell mediated by PI3K/Akt/FoxO1 signaling pathway.
Cheng, X; Gao, Y; Liao, G; Ou, Y; Xiang, C; Yang, X, 2016
)
0.43
" A significant increase in free amino groups was observed in TBs with a dose-response effect, while addition of PEF in bread produced a significant decrease (p<0."( Effect of theanine and polyphenols enriched fractions from decaffeinated tea dust on the formation of Maillard reaction products and sensory attributes of breads.
Andlauer, W; Culetu, A; del Castillo, MD; Fernandez-Gomez, B; Ullate, M, 2016
)
0.43
" The toxic effects of Cd were alleviated by exogenously applied MG in a dosage dependent fashion, and 700 mM MG reached significant differences, but this alleviating effect was eliminated by the treatment with N-acetyl-L-cysteine (NAC, MG scavenger), suggesting that MG could mitigate Cd toxicity in wheat."( Methylglyoxal alleviates cadmium toxicity in wheat (Triticum aestivum L).
Duan, XQ; Li, ZG; Min, X; Wang, Y; Xia, YM; Zhou, ZH, 2017
)
0.46
" To establish a dose-response relationship, we used inflation testing to simulate the effects of increasing intraocular pressure in freshly harvested rat eyes stiffened with multiple concentrations of each agent."( Quantification of the efficacy of collagen cross-linking agents to induce stiffening of rat sclera.
Campbell, IC; Ethier, CR; Hannon, BG; Read, AT; Schwaner, SA; Sherwood, JM, 2017
)
0.46
" Compared to the NTS control group, the middle dosage (10 mg/kg/day) of SSC significantly alleviated the development of nephritis based on urine protein measurements (34."( Utilizing methylglyoxal and D-lactate in urine to evaluate saikosaponin C treatment in mice with accelerated nephrotoxic serum nephritis.
Chen, BL; Chen, SM; Hua, SC; Lee, JA; Lee, TH; Lin, CE; Lin, CY; Lin, PY; Tsai, PY, 2020
)
0.56
" The priority of the Cys reaction with different α-dicarbonyls and its dependence on the Cys dosage were investigated."( Formation Priority of Pyrazines and 2-Acetylthiazole Dependent on the Added Cysteine and Fragments of Deoxyosones during the Thermal Process of the Glycine-Ribose Amadori Compound.
Hayat, K; Ho, CT; Liu, M; Xu, H; Yu, J; Zhang, X; Zhou, T, 2022
)
0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Saccharomyces cerevisiae metaboliteAny fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae).
Escherichia coli metaboliteAny bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
propanalsAn aldehyde based on a propanal skeleton and its derivatives.
2-oxo aldehydeAny aldehyde having an oxo substituent at the 2-position.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (44)

PathwayProteinsCompounds
Metabolism14961108
The citric acid (TCA) cycle and respiratory electron transport14756
Pyruvate metabolism and Citric Acid (TCA) cycle4146
Pyruvate metabolism2026
Glycine and Serine Metabolism2452
Pyruvate Metabolism2139
Pyruvaldehyde Degradation37
Leigh Syndrome2139
Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)2139
Pyruvate Dehydrogenase Complex Deficiency2139
Dimethylglycine Dehydrogenase Deficiency2452
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)2452
Sarcosinemia2452
Non-Ketotic Hyperglycinemia2452
Hyperglycinemia, Non-Ketotic2452
Primary Hyperoxaluria II, PH22139
Pyruvate Kinase Deficiency2139
3-Phosphoglycerate Dehydrogenase Deficiency2452
Methylglyoxal Degradation IV410
Methylglyoxal Degradation III28
Methylglyoxal Degradation II25
L-Threonine Degradation to Methylglyoxal212
Methylglyoxal Degradation I39
methylglyoxal degradation III118
detoxification of reactive carbonyls in chloroplasts422
methylglyoxal degradation I110
Glycine and Serine metabolism ( Glycine and Serine metabolism )3649
Pyruvate metabolism ( Pyruvate metabolism )3027
(R)-S-Lactoyl-glutathione = Glutathione + Methyl-glyoxal ( Pyruvate metabolism )13
Renz2020 - GEM of Human alveolar macrophage with SARS-CoV-20490
lactate biosynthesis (archaea)315
acetone degradation I (to methylglyoxal)312
superpathway of methylglyoxal degradation1330
methylglyoxal degradation VII09
methylglyoxal degradation VI113
methylglyoxal degradation V215
methylglyoxal degradation I816
methylglyoxal degradation IV221
methylglyoxal degradation III78
methylglyoxal degradation II06
L-threonine degradation III (to methylglyoxal)328
chorismate biosynthesis II (archaea)930
superpathway of L-threonine metabolism2172
3-dehydroquinate biosynthesis II (archaea)623
methylglyoxal catabolism68
glyoxalase pathway012
threonine degradation III (to methylglyoxal)012
superpathway of threonine metabolism034
methylglyoxal degradation IX26
Biochemical pathways: part I0466
threonine catabolism114

Bioassays (4)

Assay IDTitleYearJournalArticle
AID1346556Human TRPA1 (Transient Receptor Potential channels)2012The Journal of biological chemistry, Aug-17, Volume: 287, Issue:34
Methylglyoxal activates nociceptors through transient receptor potential channel A1 (TRPA1): a possible mechanism of metabolic neuropathies.
AID1346556Human TRPA1 (Transient Receptor Potential channels)2012Pharmacological research, Jan, Volume: 65, Issue:1
Inhibiting TRPA1 ion channel reduces loss of cutaneous nerve fiber function in diabetic animals: sustained activation of the TRPA1 channel contributes to the pathogenesis of peripheral diabetic neuropathy.
AID1346556Human TRPA1 (Transient Receptor Potential channels)2012PloS one, , Volume: 7, Issue:5
Expression of transient receptor potential ankyrin 1 (TRPA1) and its role in insulin release from rat pancreatic beta cells.
AID1517970Inhibition of human FBPase expressed in Escherichia coli BL21 (DE3) at 500 uM using FBP as substrate incubated for 5 mins by malachite green dye based spectrophotometry relative to control2019European journal of medicinal chemistry, Dec-15, Volume: 184Discovery of novel allosteric site and covalent inhibitors of FBPase with potent hypoglycemic effects.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (2,399)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990204 (8.50)18.7374
1990's193 (8.05)18.2507
2000's478 (19.92)29.6817
2010's1069 (44.56)24.3611
2020's455 (18.97)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.27

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index32.27 (24.57)
Research Supply Index7.82 (2.92)
Research Growth Index5.00 (4.65)
Search Engine Demand Index46.54 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.27)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials34 (1.38%)5.53%
Reviews189 (7.69%)6.00%
Case Studies2 (0.08%)4.05%
Observational3 (0.12%)0.25%
Other2,230 (90.72%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]