pyruvaldehyde

General Material Information

Preferred name	pyruvaldehyde
Trivial Name	Methylglyoxal
Short Description	2-oxopropanal
Formula	C3 H4 O2
CAS Number	78-98-8
FEMA Number	2969
Flavis Number	7.001
ECHA Number	201-164-8
FDA UNII	722KLD7415
Nikkaji Number	J1.489C
Beilstein Number	0906750
MDL	MFCD00006960
COE Number	105
xLogP3-AA	-0.40 (est)
Bio Activity Summary	External link
NMR Predictor	External link
JECFA Food Flavoring	937 pyruvaldehyde
FDA Patent	No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm	78-98-8 ; PYRUVALDEHYDE
Synonyms	acetalformaldehyde acetyl formaldehyde acetylformaldehyde acetylformyl aldehyde, pyruvic glycidylaldehyde glyoxal, methyl methyl glyoxal methyl-glyoxal methylglyoxal 2-oxo propanal 2-oxo- propanal propanal, 2-oxo- 1,2-propanedione 2-keto propionaldehyde 2-oxo propionaldehyde 2-oxo- propionaldehyde a-keto propionaldehyde keto propionaldehyde propionaldehyde, 2-keto propionaldehyde, 2-oxo- a-keto propionic aldehyde alpha-keto propionic aldehyde PVL pyroracemic aldehyde pyruvaldehyde 40% solution in water pyruvic aldehyde pyruvicaldehyde 2-oxopropanal α-Ketopropionaldehyde 2-Ketopropionaldehyde 2-Oxopropionaldehyde NSC 626580 NSC 79019 MeSH ID: D011765

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

	2-oxopropanal
NIST Chemistry WebBook:	Search Inchi
Canada Domestic Sub. List:	78-98-8
Pubchem (cid):	880
Pubchem (sid):	134971237

Publications by PubMed
Formation of 4(5)-methylimidazole and its precursors, Î±-dicarbonyl compounds, in Maillard model systems.
Cytotoxicity of Î±-dicarbonyl compounds submitted to in vitro simulated digestion process.
Response surface methodology as optimization strategy for reduction of reactive carbonyl species in foods by means of phenolic chemistry.
Effect of in vitro digestion on free Î±-dicarbonyl compounds in balsamic vinegars.
Reactivity of thermally treated Î±-dicarbonyl compounds.
Effects of monascin on anti-inflammation mediated by Nrf2 activation in advanced glycation end product-treated THP-1 monocytes and methylglyoxal-treated wistar rats.
Determination of toxic Î±-dicarbonyl compounds, glyoxal, methylglyoxal, and diacetyl, released to the headspace of lipid commodities upon heat treatment.
Antiglycative effect of fruit and vegetable seed extracts: inhibition of AGE formation and carbonyl-trapping abilities.
Non-enzymatic glycation of melamine with sugars and sugar like compounds.
Studies on the formation of methylglyoxal from dihydroxyacetone in Manuka (Leptospermum scoparium) honey.
Resveratrol upregulates Nrf2 expression to attenuate methylglyoxal-induced insulin resistance in Hep G2 cells.
Trapping of methylglyoxal by curcumin in cell-free systems and in human umbilical vein endothelial cells.
1,2-dicarbonyl compounds in commonly consumed foods.
Classification and characterization of manuka honeys based on phenolic compounds and methylglyoxal.
Short communication: Evidence for methylglyoxal-mediated browning of Parmesan cheese during low temperature storage.
Flavour chemistry of methylglyoxal and glyoxal.
Survey of 1,2-dicarbonyl compounds in commercial honey of different floral origin.
Effect of coffee filtrate, methylglyoxal, glyoxal, and caffeine on Salmonella typhimurium and S. enteritidis survival in ground chicken breasts.
Methylglyoxal, advanced glycation end products and autism: is there a connection?
Phlorotannins from brown algae (Fucus vesiculosus) inhibited the formation of advanced glycation endproducts by scavenging reactive carbonyls.
Formation of early and advanced Maillard reaction products correlates to the ripening of cheese.
Chemical modifications of peptides and their impact on food properties.
Cranberry phytochemicals inhibit glycation of human hemoglobin and serum albumin by scavenging reactive carbonyls.
Efficiency of trapping methylglyoxal by phenols and phenolic acids.
Formation of arginine modifications in a model system of NÎ±-tert-butoxycarbonyl (Boc)-arginine with methylglyoxal.
Bacterial metabolic 'toxins': a new mechanism for lactose and food intolerance, and irritable bowel syndrome.
Methylglyoxal content in drinking coffee as a cytotoxic factor.
Maternally transmitted and food-derived glycotoxins: a factor preconditioning the young to diabetes?
Beneficial effects of cinnamon proanthocyanidins on the formation of specific advanced glycation endproducts and methylglyoxal-induced impairment on glucose consumption.
Carbonyl compounds methylglyoxal and glyoxal affect interleukin-8 secretion in intestinal cells by superoxide anion generation and activation of MAPK p38.
Analysis, distribution, and dietary exposure of glyoxal and methylglyoxal in cookies and their relationship with other heat-induced contaminants.
Stilbene glucoside from Polygonum multiflorum Thunb.: a novel natural inhibitor of advanced glycation end product formation by trapping of methylglyoxal.
Carbonated soft drinks and carbonyl stress burden.
Characterization and the possible formation mechanism of 2-acetyl-1-pyrroline in aromatic vegetable soybean (Glycine max L.).
Food derived carbonyl compounds affect basal and stimulated secretion of interleukin-6 and -8 in Caco-2 cells.
Protein glycation inhibitors from the fruiting body of Phellinus linteus.
Inhibitory effect of vanillic acid on methylglyoxal-mediated glycation in apoptotic Neuro-2A cells.
Biosynthetic mechanism of 2-acetyl-1-pyrroline and its relationship with Delta1-pyrroline-5-carboxylic acid and methylglyoxal in aromatic rice (Oryza sativa L.) callus.
Identification and monitoring of intermediates and products in the acrylamide pathway using online analysis.
Formate excretion in urine of rats fed dimethylaminoazobenzene-rich diets: the possibility of formate formation from D-lactate.
Formation of 2,5-dimethyl-4-hydroxy-3(2H)-furanone through methylglyoxal: a Maillard reaction intermediate.
Ultra performance liquid chromatography-mass spectrometric determination of the site specificity of modification of beta-casein by glucose and methylglyoxal.
Methylglyoxal: its presence and potential scavengers.
Cytoprotective effects of phenolic acids on methylglyoxal-induced apoptosis in Neuro-2A cells.
Methylglyoxal: its presence in beverages and potential scavengers.
Formation of pyrazines and a novel pyrrole in Maillard model systems of 1,3-dihydroxyacetone and 2-oxopropanal.
Cinnamon bark proanthocyanidins as reactive carbonyl scavengers to prevent the formation of advanced glycation endproducts.
Identification and quantification of methylglyoxal as the dominant antibacterial constituent of Manuka (Leptospermum scoparium) honeys from New Zealand.
Methylglyoxal and other carbohydrate metabolites induce lanthanum-sensitive Ca2+ transients and inhibit growth in E. coli.
Isolation and determination of alpha-dicarbonyl compounds by RP-HPLC-DAD in green and roasted coffee.
Determination of glyoxal and methylglyoxal in environmental and biological matrices by stir bar sorptive extraction with in-situ derivatization.
Reducing the formation of glucose degradation products in peritoneal dialysis solutions by ultrahigh temperature ohmic heating.
Synthesis of 1-piperideine-6-carboxylic acid produced by L-lysine-epsilon-aminotransferase from the Streptomyces clavuligerus gene expressed in Escherichia coli.
Changes in the volatile composition of a semihard ewe milk cheese induced by high-pressure treatment of 300 MPa.
Effects of high pressure treatment on volatile profile during ripening of ewe milk cheese.
Investigations on the promoting effect of ammonium hydrogencarbonate on the formation of acrylamide in model systems.
Characterization of the glyoxalase I gene from the vascular wilt fungus Verticillium dahliae.
Trapping reactions of reactive carbonyl species with tea polyphenols in simulated physiological conditions.
Methylglyoxal in food and living organisms.
Free glutamine as a major precursor of brown products and fluorophores in Maillard reaction systems.
Epicatechin carbonyl-trapping reactions in aqueous maillard systems: Identification and structural elucidation.
Methylglyoxal-derived beta-carbolines formed from tryptophan and its derivates in the Maillard reaction.
Identification of DNA adducts of methylglyoxal.
Application of semiquantitative proteomics techniques to the maillard reaction.
Evaluation of advanced glycation end products and carbonyl compounds in patients with different conditions of oxidative stress.
D-lactate metabolism in starved Octopus ocellatus.
Determination of methylglyoxal in ruminal fluid by high-performance liquid chromatography using fluorometric detection.
Formation of genotoxic dicarbonyl compounds in dietary oils upon oxidation.
Evidence that high-dose L-arginine may be inappropriate for use by diabetic patients as a prophylactic blocker of methylglyoxal glycation.
Dietary glycotoxins correlate with circulating advanced glycation end product levels in renal failure patients.
Kinetic modelling of Amadori N-(1-deoxy-D-fructos-1-yl)-glycine degradation pathways. Part I--reaction mechanism.
Improved superoxide-generating system suitable for the assessment of the superoxide-scavenging ability of aqueous extracts of food constituents using ultraweak chemiluminescence.
Inflammatory mediators are induced by dietary glycotoxins, a major risk factor for diabetic angiopathy.
Possible mechanism for involvement of cysteine in aroma production in wine.
Qualitative determination of specific protein glycation products by matrix-assisted laser desorption/ionization mass spectrometry Peptide mapping.
Carbohydrate and amino acid degradation pathways in L-methionine/D-[13C] glucose model systems.
N(delta)-(5-hydroxy-4,6-dimethylpyrimidine-2-yl)-l-ornithine, a novel methylglyoxal-arginine modification in beer.
Inhibition of gastric mucosal damage by methylglyoxal pretreatment in rats.
Origin of carbohydrate degradation products in L-Alanine/D-[(13)C]glucose model systems.
Performance of a 62Zn/62Cu generator in clinical trials of PET perfusion agent 62Cu-PTSM.
Origin of 2,3-pentanedione and 2,3-butanedione in D-glucose/L-alanine Maillard model systems.
Toxicity of low levels of methylglyoxal: depletion of blood glutathione and adverse effect on glucose tolerance in mice.
Methylglyoxal modification of protein. Chemical and immunochemical characterization of methylglyoxal-arginine adducts.
Generation and the fate of C2, C3, and C4 reactive fragments formed in Maillard model systems of [13C]glucose and [13C]glycine or proline.
Protein modification by a Maillard reaction intermediate methylglyoxal. Immunochemical detection of fluorescent 5-methylimidazolone derivatives in vivo.
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.
Methylglyoxal and regulation of its metabolism in microorganisms.
Analysis of the potential carcinogenicity of coffee and its related compounds in a medium-term liver bioassay of rats.
Methylglyoxal and lipid hydroxperoxide as endogenous cytotoxic molecular species: detoxification and regulation of gene expression in yeasts.
Glyoxalase I in micro-organisms: molecular characteristics, genetics and biochemical regulation.
Concentrations of D-lactate and its related metabolic intermediates in liver, blood, and muscle of diabetic and starved rats.
2-Oxoaldehyde metabolism in microorganisms.
Contribution of coffee aroma constituents to the mutagenicity of coffee.
L-alanine: 4,5-dioxovalerate aminotransferase from Pseudomonas riboflavina: purification and inactivation by methylglyoxal.
Metabolism of 2-oxoaldehyde in mold. Purification and characterization of two methylglyoxal reductases from Aspergillus niger.
Metabolism of 2-ketoaldehydes in mold: purification and characterization of glyoxalase I from Aspergillus niger.
Simple and sensitive determination of methylglyoxal in biological samples by gas chromatography with electron-capture detection.
Mutagens in coffee and other beverages.
Methylglyoxal in beverages and foods: its mutagenicity and carcinogenicity.
Mutagens and carcinogens in foods.
Bacterial mutagenicity of natural materials, pyrolysis products and additives in foodstuffs and their association with genotoxic effects in mammals.
Rapid, sensitive assay for staphylococcal enterotoxin and a comparison of serological methods.
Publications by J-Stage
Cleavage of a-Dicarbonyl Compounds by Terpene Hydroperoxide

Other Information

(IUPAC):	Atomic Weights of the Elements 2011 (pdf)
Videos:	The Periodic Table of Videos
tgsc:	Atomic Weights use for this web site
(IUPAC):	Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):	View
CHEBI:	View
CHEMBL:	View
Golm Metabolome Database:	Search
KEGG (GenomeNet):	C00546
HMDB (The Human Metabolome Database):	HMDB01167
FooDB:	FDB008295
YMDB (Yeast Metabolome Database):	YMDB00170
Export Tariff Code:	2914.49.5000
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
Formulations/Preparations: supplied commercially as a 30% aqueous solution.

Suppliers

BOC Sciences	Penta International
Santa Cruz Biotechnology	Sigma-Aldrich
United International	Penta International Corporation
Qingdao Free Trade Zone United International Co Ltd

PhysChem Properties

Material listed in food chemical codex	No
Molecular weight	72.063278198242
Acid Value	10 max KOH/g
Vapor Pressure	120.93 mmHg @ 25 °C
Flash Point TCC Value	2.22 °C TCC
logP (o/w)	-1.5
Solubility
alcohol	Yes
water, 1e+006 mg/L @ 25 °C (est)	Yes

Organoleptic Properties

Odor Type: Caramellic
sweet, acidic, ethereal, brown, rummy
General comment	At 1.00 % in propylene glycol. sweet acidic ethereal brown rum
Mosciano, Gerard P&F 17, No. 5, 127, (1992)	Sweet, acidic, etherial, brown, with a rummy nuance
Flavor Type: Caramellic
sweet, caramellic, dairy, creamy
Mosciano, Gerard P&F 17, No. 5, 127, (1992)	At 0.10 %. Sweet, caramellic with a dairy creamy nuance

Occurrences

Potential Uses

Applications	flavoring agents
Flavoring purposes	Caramel , Coffee , Maple , Rum

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 11 - Highly flammable. R 22 - Harmful if swallowed. R 36 - Irritating to eyes. S 02 - Keep out of the reach of children. S 16 - Keep away from sources of ignition - No Smoking. S 20/21 - When using do not eat, drink or smoke. S 24/25 - Avoid contact with skin and eyes. S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S 37/39 - Wear suitable gloves and eye/face protection.

Hazards identification

Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements

Pictogram

Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 1165 mg/kg Ecotoxicology and Environmental Safety. Vol. 2, Pg. 369, 1978. intravenous-mouse LD50 252 mg/kg Cesko-Slovenska Farmacie. Vol. 15, Pg. 300, 1966. intraperitoneal-mouse LD50 179 mg/kg National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavoring agents
Recommendation for pyruvaldehyde usage levels up to:
	not for fragrance use.

Maximised Survey-derived Daily Intakes (MSDI-EU):		99.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA):		3.00 (μg/capita/day)
Structure Class:		I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
		average usual ppm	average maximum ppm
baked goods:		0.03000	5.00000
beverages(nonalcoholic):		-	1.00000
beverages(alcoholic):		-	-
breakfast cereal:		-	-
cheese:		-	-
chewing gum:		-	-
condiments / relishes:		-	-
confectionery froastings:		-	-
egg products:		-	-
fats / oils:		-	-
fish products:		-	-
frozen dairy:		-	1.00000
fruit ices:		-	1.00000
gelatins / puddings:		-	-
granulated sugar:		-	-
gravies:		-	-
hard candy:		0.03000	5.00000
imitation dairy:		-	-
instant coffee / tea:		-	-
jams / jellies:		-	-
meat products:		-	-
milk products:		-	-
nut products:		-	-
other grains:		-	-
poultry:		-	-
processed fruits:		-	-
processed vegetables:		-	-
reconstituted vegetables:		-	-
seasonings / flavors:		-	-
snack foods:		-	-
soft candy:		-	-
soups:		-	-
sugar substitutes:		-	-
sweet sauces:		-	-

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 64 (FGE.64): Consideration of aliphatic acyclic diols, triols, and related substances evaluated by JECFA (57th meeting) structurally related to aliphatic primary and secondary saturated and unsaturated alcohols, aldehydes, acetals, carboxylic acids and esters containing an additional oxygenated functional group and lactones from chemical groups 9, 13 and 30 evaluated by EFSA in FGE.10Rev1 (EFSA, 2008ab)
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EPI System: View

Daily Med:search

Chemical Carcinogenesis Research Information System:Search

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA GENetic TOXicology:Search

EPA Substance Registry Services (TSCA):78-98-8

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :880

National Institute of Allergy and Infectious Diseases:Data