Pyruvic acid - wikipedia Pyruvic acid Pyruvic acid Names Preferred IUPAC name 2 - Oxopropanoic acid Other names Pyruvic acid α - Ketopropionic acid Acetylformic acid Pyroracemic acid Identifiers CAS Number 127 - 17 - 3 3D model ( JSmol ) Interactive image Abbreviations Pyr ChEBI CHEBI : 32816 ChemSpider 1031 DrugBank DB00119 ECHA InfoCard 100.004. 387 IUPHAR / BPS 4809 KEGG C00022 PubChem CID 1060 UNII 8558G7RUTR InChI InChI = 1S / C3H4O3 / c1 - 2 ( 4 ) 3 ( 5 ) 6 / h1H3, ( H, 5, 6 ) Key : LCTONWCANYUPML - UHFFFAOYSA - N SMILES O = C ( C ( = O ) O ) C Properties Chemical formula C H O Molar mass 88.06 g / mol Density 1.250 g / cm Melting point 11.8 ° C ( 53.2 ° F ; 284.9 K ) Boiling point 165 ° C ( 329 ° F ; 438 K ) Acidity ( pK ) 2.50 Related compounds Other anions pyruvate ion Related keto - acids, carboxylic acids acetic acid glyoxylic acid oxalic acid propionic acid acetoacetic acid Related compounds propionaldehyde glyceraldehyde methylglyoxal sodium pyruvate Except where otherwise noted, data are given for materials in their standard state ( at 25 ° C ( 77 ° F ), 100 kPa ). N verify ( what is ? ) Infobox references Pyruvic acid ( CH COCOOH ) is the simplest of the alpha - keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH COCOO, is a key intermediate in several metabolic pathways. Pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates ( such as glucose ) via gluconeogenesis, or to fatty acids through a reaction with acetyl - CoA. It can also be used to construct the amino acid alanine and can be converted into ethanol or lactic acid via fermentation. Pyruvic acid supplies energy to cells through the citric acid cycle ( also known as the Krebs cycle ) when oxygen is present ( aerobic respiration ), and alternatively ferments to produce lactate when oxygen is lacking ( fermentation ). Contents 1 Chemistry 2 Biochemistry 2.1 Pyruvic acid production by glycolysis 2.2 Decarboxylation to acetyl CoA 2.3 Carboxylation to oxaloacetate 2.4 Transamination to alanine 2.5 Reduction to lactate 3 Uses 4 See also 5 Notes 6 References 7 External links Chemistry In 1834, Théophile - Jules Pelouze distilled both tartaric acid ( L - tartaric acid ) and racemic acid ( a mix of D - and L - tartaric acid ) and isolated pyrotartaric acid ( methyl succinic acid ) and another acid that Jöns Jacob Berzelius characterized the following year and named pyruvic acid. Pyruvic acid is a colorless liquid with a smell similar to that of acetic acid and is miscible with water. In the laboratory, pyruvic acid may be prepared by heating a mixture of tartaric acid and potassium hydrogen sulfate, by the oxidation of propylene glycol by a strong oxidizer ( e.g., potassium permanganate or bleach ), or by the hydrolysis of acetyl cyanide, formed by reaction of acetyl chloride with potassium cyanide : CH COCl + KCN → CH COCN + KCl CH COCN → CH COCOOH Biochemistry Pyruvate is an important chemical compound in biochemistry. It is the output of the metabolism of glucose known as glycolysis. One molecule of glucose breaks down into two molecules of pyruvate, which are then used to provide further energy, in one of two ways. Pyruvate is converted into acetyl - coenzyme A, which is the main input for a series of reactions known as the Krebs cycle ( also known as the citric acid cycle or tricarboxylic acid cycle ). Pyruvate is also converted to oxaloacetate by an anaplerotic reaction, which replenishes Krebs cycle intermediates ; also, the oxaloacetate is used for gluconeogenesis. These reactions are named after Hans Adolf Krebs, the biochemist awarded the 1953 Nobel Prize for physiology, jointly with Fritz Lipmann, for research into metabolic processes. The cycle is also known as the citric acid cycle or tricarboxylic acid cycle, because citric acid is one of the intermediate compounds formed during the reactions. If insufficient oxygen is available, the acid is broken down anaerobically, creating lactate in animals and ethanol in plants and microorganisms ( and carp ). Pyruvate from glycolysis is converted by fermentation to lactate using the enzyme lactate dehydrogenase and the coenzyme NADH in lactate fermentation, or to acetaldehyde ( with the enzyme pyruvate decarboxylase ) and then to ethanol in alcoholic fermentation. Pyruvate is a key intersection in the network of metabolic pathways. Pyruvate can be converted into carbohydrates via gluconeogenesis, to fatty acids or energy through acetyl - CoA, to the amino acid alanine, and to ethanol. Therefore, it unites several key metabolic processes. Reference ranges for blood tests, comparing blood content of pyruvate ( shown in violet near middle ) with other constituents. Pyruvic acid production by glycolysis In glycolysis, phosphoenolpyruvate ( PEP ) is converted to pyruvate by pyruvate kinase. This reaction is strongly exergonic and irreversible ; in gluconeogenesis, it takes two enzymes, pyruvate carboxylase and PEP carboxykinase, to catalyze the reverse transformation of pyruvate to PEP. phosphoenolpyruvate pyruvate kinase pyruvate ADP ATP ADP ATP pyruvate carboxylase and PEP carboxykinase Compound C00074 at KEGG Pathway Database. Enzyme 2.7. 1.40 at KEGG Pathway Database. Compound C00022 at KEGG Pathway Database. Click on genes, proteins and metabolites below to link to respective articles. 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Decarboxylation to acetyl CoA Pyruvate decarboxylation by the pyruvate dehydrogenase complex produces acetyl - CoA. pyruvate pyruvate dehydrogenase complex acetyl - CoA CoA + NAD CO + NADH + H Carboxylation to oxaloacetate Carboxylation by pyruvate carboxylase produces oxaloacetate. pyruvate pyruvate carboxylase oxaloacetate ATP + CO ADP + P Transamination to alanine Transamination by alanine transaminase produces alanine. pyruvate alanine transaminase alanine glutamate α - ketoglutarate glutamate α - ketoglutarate Reduction to lactate Reduction by lactate dehydrogenase produces lactate. pyruvate lactate dehydrogenase lactate NADH NAD NADH NAD Uses Pyruvate is sold as a weight - loss supplement, though evidence supporting this use is lacking. A systematic review of six trials found a statistically significant difference in body weight with pyruvate compared to placebo. However, all of the trials had methodological weaknesses and the magnitude of the effect was small. The review also identified adverse events associated with pyruvate such as diarrhea, bloating, gas, and increase in low - density lipoprotein ( LDL ) cholesterol. The authors concluded that there was insufficient evidence to support the use of pyruvate for weight loss. There is also in vitro as well as in vivo evidence in hearts that pyruvate improves metabolism by NADH production stimulation and increases cardiac function. See also Pyruvate scale Notes ^ Jump up to : Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 ( Blue Book ). Cambridge : The Royal Society of Chemistry. 2014. p. 748. ISBN 978 - 0 - 85404 - 182 - 4. doi : 10.1039 / 9781849733069 - FP001. Jump up ^ Dawson, R.M.C. ; et al. ( 1959 ). Data for Biochemical Research. Oxford : Clarendon Press. Jump up ^ Fox, Stuart Ira ( 2011 ). Human Physiology ( 12th ed. ). McGraw = Hill. p. 146. Jump up ^ Ophardt, Charles E. `` Pyruvic Acid - Cross Roads Compound ''. Virtual Chembook. Elmhurst College. Retrieved April 7, 2017. Jump up ^ Thomson, Thomas ( 1838 ). `` Chapter II. Of fixed acids Section ''. Chemistry of organic bodies, vegetables. London : J.B. Baillière. p. 65. Retrieved December 1, 2010. Jump up ^ Thorpe, Thomas Edward ( 1922 ). `` Glutaric acid ''. A dictionary of applied chemistry. 3. London : Longmans, Green, and Co. pp. 426 -- 427. Retrieved December 1, 2010. Jump up ^ `` Pyruvic Acid ''. ChemSpider. Royal Society of Chemistry. Retrieved 21 April 2017. Jump up ^ Howard, J.W. ; Fraser, W.A. `` Pyruvic Acid ''. Org. Synth. 4 : 63. ; Coll. Vol., 1, p. 475 ^ Jump up to : Lehninger, Albert L. ; Nelson, David L. ; Cox, Michael M. ( 2008 ). Principles of Biochemistry ( 5th ed. ). New York, NY : W.H. Freeman and Company. p. 528. ISBN 978 - 0 - 7167 - 7108 - 1. Jump up ^ Aren van Waarde ; G. Van den Thillart ; Maria Verhagen ( 1993 ). `` Ethanol Formation and pH - Regulation in Fish ''. Surviving Hypoxia. pp. 157 -- 170. ISBN 0 - 8493 - 4226 - 0. Jump up ^ Onakpoya, I. ; Hunt, K. ; Wider, B. ; Ernst, E. ( 2014 ). `` Pyruvate supplementation for weight loss : a systematic review and meta - analysis of randomized clinical trials ''. Crit. Rev. Food Sci. Nutr. 54 ( 1 ) : 17 -- 23. PMID 24188231. doi : 10.1080 / 10408398.2011. 565890. Jump up ^ Jaimes, R., III ( Jul 2015 ). `` Functional response of the isolated, perfused normoxic heart to pyruvate dehydrogenase activation by dichloroacetate and pyruvate. ''. Pflugers Arch. 468 : 131 -- 42. PMC 4701640. PMID 26142699. doi : 10.1007 / s00424 - 015 - 1717 - 1. Jump up ^ Hermann, H.P. ; Pieske, B. ; Schwarzmüller, E. ; Keul, J. ; Just, H. ; Hasenfuss, G. ( 1999 - 04 - 17 ). `` Haemodynamic effects of intracoronary pyruvate in patients with congestive heart failure : an open study ''. Lancet. 353 ( 9161 ) : 1321 -- 1323. ISSN 0140 - 6736. PMID 10218531. doi : 10.1016 / s0140 - 6736 ( 98 ) 06423 - x. References Cody, G.D. ; Boctor, N.Z. ; Filley, T.R. ; Hazen, R.M. ; Scott, J.H. ; Sharma, A. ; Yoder, H.S., Jr ( 2000 ). `` Primordial Carbonylated Iron - Sulfur Compounds and the Synthesis of Pyruvate ''. Science. 289 ( 5483 ) : 1337 -- 1340. Bibcode : 2000Sci... 289.1337 C. PMID 10958777. doi : 10.1126 / science. 289.5483. 1337. External links Pyruvic acid mass spectrum Wikimedia Commons has media related to Pyruvic acid. Glycolysis metabolic pathway Glucose Hexokinase ATP ADP Glucose 6 - phosphate Glucose - 6 - phosphate isomerase Fructose 6 - phosphate phosphofructokinase - 1 ATP ADP Fructose 1, 6 - bisphosphate Fructose - bisphosphate aldolase Dihydroxyacetone phosphate + + Glyceraldehyde 3 - phosphate Triosephosphate isomerase 2 × Glyceraldehyde 3 - phosphate 2 × Glyceraldehyde - 3 - phosphate dehydrogenase NAD + P NADH + H NAD + P NADH + H 2 × 1, 3 - Bisphosphoglycerate 2 × Phosphoglycerate kinase ADP ATP ADP ATP 2 × 3 - Phosphoglycerate 2 × Phosphoglycerate mutase 2 × 2 - Phosphoglycerate 2 × Phosphopyruvate hydratase ( Enolase ) H O H O 2 × Phosphoenolpyruvate 2 × Pyruvate kinase ADP ATP 2 × Pyruvate 2 × Amino acid metabolism metabolic intermediates K → acetyl - CoA lysine → Saccharopine Allysine α - Aminoadipic acid α - Ketoadipate Glutaryl - CoA Glutaconyl - CoA Crotonyl - CoA β - Hydroxybutyryl - CoA leucine → α - Ketoisocaproic acid β - hydroxy β - methylbutyric acid β - hydroxy β - methylbutyryl - CoA Isovaleryl - CoA 3 - Methylcrotonyl - CoA 3 - Methylglutaconyl - CoA HMG - CoA tryptophan → alanine → N ' - Formylkynurenine Kynurenine Anthranilic acid 3 - Hydroxykynurenine 3 - Hydroxyanthranilic acid 2 - Amino - 3 - carboxymuconic semialdehyde 2 - Aminomuconic semialdehyde 2 - Aminomuconic acid Glutaryl - CoA G → pyruvate → citrate glycine → serine → 3 - Phosphoglyceric acid glycine → creatine : Glycocyamine Phosphocreatine Creatinine G → glutamate → α - ketoglutarate histidine → Urocanic acid Imidazol - 4 - one - 5 - propionic acid Formiminoglutamic acid Glutamate - 1 - semialdehyde proline → 1 - Pyrroline - 5 - carboxylic acid arginine → Agmatine Ornithine Citrulline Cadaverine Putrescine other cysteine + glutamate → glutathione : γ - Glutamylcysteine G → propionyl - CoA → succinyl - CoA valine → α - Ketoisovaleric acid Isobutyryl - CoA Methacrylyl - CoA 3 - Hydroxyisobutyryl - CoA 3 - Hydroxyisobutyric acid 2 - Methyl - 3 - oxopropanoic acid isoleucine → 2, 3 - Dihydroxy - 3 - methylpentanoic acid 2 - Methylbutyryl - CoA Tiglyl - CoA 2 - Methylacetoacetyl - CoA methionine → generation of homocysteine : S - Adenosyl methionine S - Adenosyl - L - homocysteine Homocysteine conversion to cysteine : Cystathionine alpha - Ketobutyric acid + Cysteine threonine → α - Ketobutyric acid propionyl - CoA → Methylmalonyl - CoA G → fumarate phenylalanine → tyrosine → 4 - Hydroxyphenylpyruvic acid Homogentisic acid 4 - Maleylacetoacetic acid G → oxaloacetate see urea cycle Other Cysteine metabolism Cysteine sulfinic acid LCCN : sh85109371 GND : 4337268 - 5 Retrieved from `` https://en.wikipedia.org/w/index.php?title=Pyruvic_acid&oldid=806975253 '' Categories : Glycolysis Keto acids Cellular respiration Exercise physiology Metabolism Hidden categories : Pages with missing ISBNs Articles without InChI source ECHA InfoCard ID from Wikidata Articles with changed KEGG identifier Articles containing unverified chemical infoboxes Wikipedia articles with LCCN identifiers Wikipedia articles with GND identifiers Talk Contents About Wikipedia Български Bosanski Català Čeština Dansk Deutsch Ελληνικά Español Esperanto Euskara فارسی Français Gaeilge Galego 한국어 Հայերեն हिन्दी Hrvatski Bahasa Indonesia Italiano עברית ქართული Latviešu Lëtzebuergesch Magyar Македонски Bahasa Melayu Nederlands 日本 語 Norsk Polski Português Română Русский Sicilianu Simple English Српски / srpski Srpskohrvatski / српскохрватски Suomi Svenska ไทย Türkçe Українська 粵語 中文 Edit links This page was last edited on 25 October 2017, at 05 : 39. 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Question: in the absence of oxygen muscle cells may convert pyruvic acid into what compound
Answer: lactate