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Revision as of 09:53, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464363019 of page Pyruvic_acid for the Chem/Drugbox validation project (updated: '').		Latest revision as of 16:49, 12 December 2024 edit Freaky.jpeg (talk | contribs)37 editsmNo edit summary
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			{{short description|Simplest of the alpha-keto acids}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
	| Verifiedfields = changed		| Verifiedfields = changed
			| Watchedfields = changed
	| verifiedrevid = 413631436
			| verifiedrevid = 464364811
	| Name = Pyruvic acid
	| ImageFileL1_Ref = {{chemboximage|correct|??}}		| Name = Pyruvic acid
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageFileL1 = Pyruvic-acid-2D-skeletal.png		| ImageFileL1 = Brenztraubensäure.svg
			| ImageClassL1 = skin-invert-image
	| ImageSizeL1 = 120px
	| ImageFileR1 = Pyruvic-acid-3D-balls.png		| ImageFileR1 = Pyruvic-acid-3D-balls.png
			| PIN = 2-Oxopropanoic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 748 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
	| ImageSizeR1 = 120px
	| IUPACName = 2-oxopropanoic acid		| SystematicName = 2-Oxopropionic acid
			| OtherNames = Pyruvic acid<ref name=iupac2013 /><br />α-Ketopropionic acid<br />Acetylformic acid<br />Pyroracemic acid<br/>Acetylcarboxylic acid
	| OtherNames = α-ketopropionic acid; acetylformic acid; pyroracemic acid; Pyr
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| PubChem = 1060		| IUPHAR_ligand = 4809
			| PubChem = 1060
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 8558G7RUTR		| UNII = 8558G7RUTR
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = LCTONWCANYUPML-UHFFFAOYSA-N		| StdInChIKey = LCTONWCANYUPML-UHFFFAOYSA-N
			| Abbreviations = Pyr
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 127-17-3		| CASNo = 127-17-3
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 1031		| ChemSpiderID = 1031
	| DrugBank_Ref = {{drugbankcite|changed|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB00119		| DrugBank = DB00119
	| ChEBI_Ref = {{ebicite|changed|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 32816		| ChEBI = 32816
			| KEGG_Ref = {{keggcite|changed|kegg}}
			| KEGG = C00022
	| SMILES = O=C(C(=O)O)C		| SMILES = O=C(C(=O)O)C
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula = C<sub>3</sub>H<sub>4</sub>O<sub>3</sub>		| Formula = C<sub>3</sub>H<sub>4</sub>O<sub>3</sub>
	| MolarMass = 88.06 g/mol		| MolarMass = 88.06{{nbsp}}g/mol
	| Density = 1.250 g/cm³		| Density = 1.250{{nbsp}}g/cm<sup>3</sup>
	| MeltingPtC = 11.8		| MeltingPtC = 11.8
	| BoilingPtC = 165		| BoilingPtC = 165
	| pKa = 2.50<ref>Dawson, R. M. C. et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959.</ref>		| pKa = 2.50<ref>{{cite book|last=Dawson|first=R. M. C.|display-authors=etal|title=Data for Biochemical Research|location= Oxford|publisher= Clarendon Press|date= 1959}}</ref>
	}}
	| Section4 = {{Chembox Related
	| OtherAnions = pyruvate ion<br /> ]&nbsp;&nbsp;&nbsp;]
	| Function = ]s, ]s
	| OtherFunctn = ]<br />]<br />]<br />]<br />]
	| OtherCpds = ]<br />]<br />]<br />]
	}}
	}}		}}
			| Section4 = {{Chembox Related
			| OtherAnions = ]<br /> ]<br />]
			| OtherFunction_label = ]s, ]s
			| OtherFunction = {{ubl
			| ]
			| ]
			| ]
			| ]
			| ]
			}}
			| OtherCompounds = {{ubl
			| ]
			| ]
			| ]
			| ]
			}}
			}}
			}}
			'''Pyruvic acid''' (CH<sub>3</sub>COCOOH) is the simplest of the ], with a ] and a ] functional group. '''Pyruvate''', the ], CH<sub>3</sub>COCOO<sup>−</sup>, is an ] in several ]s throughout the cell.
			Pyruvic acid can be made from ] through ], converted back to ]s (such as glucose) via ], or converted to ]s through a reaction with ].<ref>{{cite book|first=Stuart Ira|last= Fox|title= Human Physiology|edition=12th|publisher=McGraw=Hill|date=2011|page=146}}{{ISBN missing}}</ref> It can also be used to construct the amino acid ] and can be converted into ] or ] via ].
			Pyruvic acid supplies energy to ] through the ] (also known as the Krebs cycle) when oxygen is present (]), and alternatively ] to produce ] when oxygen is lacking.<ref>{{cite web|last1=Ophardt|first1=Charles E.|title=Pyruvic Acid - Cross Roads Compound|url=http://chemistry.elmhurst.edu/vchembook/603pyruvic.html|website=Virtual Chembook|publisher=Elmhurst College|access-date=April 7, 2017|archive-date=July 31, 2018|archive-url=https://web.archive.org/web/20180731021548/http://chemistry.elmhurst.edu/vchembook/603pyruvic.html}}</ref>
			==Chemistry==
			In 1834, ] distilled ] and isolated ] and another unknown organic acid. ] characterized this other acid the following year and named pyruvic acid because it was distilled using heat.<ref>{{cite book|last=Thomson|first= Thomas |author-link=Thomas Thomson (chemist)|title=Chemistry of organic bodies, vegetables|url=https://books.google.com/books?id=Wq45AAAAcAAJ |access-date=December 1, 2010|year= 1838|publisher=J. B. Baillière|location=London|page=65|chapter=Chapter II. Of fixed acids Section|chapter-url=https://books.google.com/books?id=Wq45AAAAcAAJ&pg=PA65 }}</ref><ref>{{cite journal |last1=Berzelius |first1=J. |title=Ueber eine neue, durch Destillation von Wein-und Traubensäure erhaltene Säure |journal=Annalen der Pharmacie |date=1835 |volume=13 |issue=1 |pages=61–63 |doi=10.1002/jlac.18350130109|url=https://zenodo.org/record/1951856 }}</ref> The correct molecular structure was deduced by the 1870s.<ref>{{cite journal |doi=10.1039/CA8783400019 |title=Pyruvic acid |journal=Journal of the Chemical Society, Abstracts |year=1878 |volume=34 |page=31 }}</ref>
			Pyruvic acid is a colorless liquid with a smell similar to that of ] and is ] with water.<ref>{{cite web|title=Pyruvic Acid|url=http://www.chemspider.com/Chemical-Structure.1031.html |website=ChemSpider|publisher=Royal Society of Chemistry|access-date=21 April 2017}}</ref> In the laboratory, pyruvic acid may be prepared by heating a mixture of ] and ],<ref>{{OrgSynth|title=Pyruvic Acid|last1=Howard|first1=J. W.|last2=Fraser|first2=W. A.|prep=cv1p0475 |collvol=1| collvolpages=475 |volume=4|page=63|date=1925}}</ref> by the ] of ] by a strong oxidizer (e.g., ] or ]), or by the hydrolysis of ], formed by reaction of ] with ]:{{Citation needed|date=December 2023}}
			:CH<sub>3</sub>COCl + KCN → CH<sub>3</sub>COCN + KCl
			:CH<sub>3</sub>COCN → CH<sub>3</sub>COCOOH
			==Biochemistry==
			{{Citations needed|date=December 2023}}
			Pyruvate is an important ] in ]. It is the output of the metabolism of ] known as ].<ref name="lehninger528">{{Cite book|title=Principles of Biochemistry|edition=5th|first1=Albert L.|first2=David L.|first3=Michael M.|last1=Lehninger|last2=Nelson|last3=Cox|publisher=W. H. Freeman and Company|location=New York, NY|year=2008|isbn=978-0-7167-7108-1|page=|url-access=registration|url=https://archive.org/details/lehningerprincip00lehn_1/page/528}}</ref> One molecule of ] breaks down into two molecules of pyruvate,<ref name="lehninger528" /> which are then used to provide further energy, in one of two ways. Pyruvate is converted into ], which is the main input for a series of reactions known as the ] (also known as the citric acid cycle or tricarboxylic acid cycle). Pyruvate is also converted to ] by an ], which replenishes Krebs cycle intermediates; also, the oxaloacetate is used for ].{{Citation needed|date=December 2023}}
			These reactions are named after ], the biochemist awarded the 1953 ] for physiology, jointly with ], for research into metabolic processes. The cycle is also known as the ] or tricarboxylic acid cycle, because citric acid is one of the intermediate compounds formed during the reactions.{{Citation needed|date=December 2023}}
			If insufficient oxygen is available, the acid is broken down ], creating ] in animals and ] in plants and microorganisms (and in ]<ref>{{cite book|author1=Aren van Waarde|author2=G. Van den Thillart|author3-link=Maria Verhagen|author3=Maria Verhagen|title=Surviving Hypoxia|date=1993|isbn=0-8493-4226-0|pages=157–170|chapter=Ethanol Formation and pH-Regulation in Fish|publisher=CRC Press |author1-link=Aren van Waarde|hdl=11370/3196a88e-a978-4293-8f6f-cd6876d8c428}}</ref>). Pyruvate from glycolysis is converted by ] to ] using the ] ] and the ] ] in lactate ], or to ] (with the enzyme ]) and then to ] in ].{{Citation needed|date=December 2023}}
			Pyruvate is a key intersection in the network of ]s. Pyruvate can be converted into ]s via ], to ]s or energy through ], to the ] ], and to ]. Therefore, it unites several key metabolic processes.{{Citation needed|date=December 2023}}
			], comparing blood content of pyruvate (shown in violet near middle) with other constituents.]]
			===Pyruvic acid production by glycolysis===
			In the last step of ], ] (PEP) is converted to pyruvate by ]. This reaction is strongly exergonic and irreversible; in ], it takes two enzymes, ] and ], to catalyze the reverse transformation of pyruvate to PEP.{{Citation needed|date=December 2023}}
			{{Enzymatic reaction
			| forward_enzyme=]
			| reverse_enzyme=] and ]
			| substrate=]
			| product=pyruvic acid
			| reaction_direction_(forward/reversible/reverse)=reversible
			| minor_forward_substrate(s)=]
			| minor_forward_product(s)=]
			| minor_reverse_substrate(s)=]
			| minor_reverse_product(s)=]
			| substrate_image=phosphoenolpyruvate_wpmp.svg
			| product_image=Pyruvic-acid-2D-skeletal.svg
			| product_image_size=90px
			}}
			{{KEGG compound|C00074}} {{KEGG enzyme|2.7.1.40}} {{KEGG compound|C00022}}
			{{GlycolysisGluconeogenesis_WP534|highlight=Pyruvic_acid__alt1}}
			===Decarboxylation to acetyl CoA===
			] by the ] produces ].
			{{Enzymatic Reaction
			| forward_enzyme=]
			| reverse_enzyme=
			| substrate=pyruvate
			| product=]
			| reaction_direction_(forward/reversible/reverse)=forward
			| minor_forward_substrate(s)= ] '''+''' NAD<sup>+</sup>
			| minor_forward_product(s)= CO<sub>2</sub> '''+''' NADH '''+''' H<sup>+</sup>
			| minor_reverse_substrate(s)=
			| minor_reverse_product(s)=
			| substrate_image=pyruvate_wpmp.png
			| product_image=Acetyl-CoA.svg
			}}
			===Carboxylation to oxaloacetate===
			Carboxylation by ] produces ].
			{{Enzymatic Reaction
			| forward_enzyme=]
			| reverse_enzyme=
			| substrate=pyruvate
			| product=]
			| reaction_direction_(forward/reversible/reverse)=forward
			| minor_forward_substrate(s)= ATP '''+''' CO<sub>2</sub>
			| minor_forward_product(s)= ADP '''+''' P<sub>i</sub>
			| minor_reverse_substrate(s)=
			| minor_reverse_product(s)=
			| substrate_image=pyruvate_wpmp.png
			| product_image=Oxaloacetate_wpmp.png
			}}
			===Transamination to alanine===
			Transamination by ] produces ].
			{{Enzymatic Reaction
			| forward_enzyme=]
			| reverse_enzyme=
			| substrate=pyruvate
			| product=]
			| reaction_direction_(forward/reversible/reverse)=reversible
			| minor_forward_substrate(s)= ]
			| minor_forward_product(s)= ]
			| minor_reverse_substrate(s)= ]
			| minor_reverse_product(s)= ]
			| substrate_image=pyruvate_wpmp.png
			| product_image=L-alanine-skeletal.svg
			| product_image_size=100px
			}}
			===Reduction to lactate===
			Reduction by ] produces ].
			{{Enzymatic Reaction
			| forward_enzyme=]
			| reverse_enzyme=
			| substrate=pyruvate
			| product=]
			| reaction_direction_(forward/reversible/reverse)=reversible
			| minor_forward_substrate(s)= NADH
			| minor_forward_product(s)= NAD<sup>+</sup>
			| minor_reverse_substrate(s)= NAD<sup>+</sup>
			| minor_reverse_product(s)= NADH
			| substrate_image=pyruvate_wpmp.png
			| product_image=Lactic-acid-skeletal.svg
			}}
			=== Environmental chemistry ===
			Pyruvic acid is an abundant carboxylic acid in ]s.<ref>{{Cite journal|last1=Guzman|first1=Marcelo I.|last2=Eugene|first2=Alexis J.|date=2021-09-01|title=Aqueous Photochemistry of 2-Oxocarboxylic Acids: Evidence, Mechanisms, and Atmospheric Impact|journal=Molecules|language=en|volume=26|issue=17|page=5278|doi=10.3390/molecules26175278|pmid=34500711|pmc=8433822|doi-access=free}}</ref>
			==Uses==
			Pyruvate is sold as a ], though credible science has yet to back this claim. A ] of six ] found a statistically significant difference in body weight with pyruvate compared to ]. However, all of the trials had methodological weaknesses and the magnitude of the effect was small. The review also identified ] associated with pyruvate such as diarrhea, bloating, gas, and increase in ] (LDL) cholesterol. The authors concluded that there was insufficient evidence to support the use of pyruvate for weight loss.<ref>{{cite journal|last1=Onakpoya|first1= I.|last2= Hunt|first2= K.|last3=Wider|first3= B.|last4= Ernst |first4=E.|title=Pyruvate supplementation for weight loss: a systematic review and meta-analysis of randomized clinical trials|doi=10.1080/10408398.2011.565890|journal=Crit. Rev. Food Sci. Nutr.|date=2014|volume=54|issue=1|pages=17–23|pmid=24188231|s2cid= 20241217}}</ref>
			There is also '']'' as well as '']'' evidence in hearts that pyruvate improves metabolism by ] production stimulation and increases cardiac function.<ref name="Functional response of the isolated, perfused normoxic heart to pyruvate dehydrogenase activation by dichloroacetate and pyruvate.">{{cite journal |pmid=26142699 |title=Functional response of the isolated, perfused normoxic heart to pyruvate dehydrogenase activation by dichloroacetate and pyruvate. |last1=Jaimes |first1=R. III |doi=10.1007/s00424-015-1717-1 |date=Jul 2015 |journal=Pflügers Arch. |volume=468 |issue=1 |pmc=4701640 |pages=131–42}}</ref><ref>{{Cite journal|last1=Hermann|first1=H. P.|last2=Pieske|first2=B.|last3=Schwarzmüller|first3=E.|last4=Keul|first4=J.|last5=Just|first5=H.|last6=Hasenfuss|first6=G.|date=1999-04-17|title=Haemodynamic effects of intracoronary pyruvate in patients with congestive heart failure: an open study|journal=Lancet |volume=353|issue=9161|pages=1321–1323|issn=0140-6736|pmid=10218531|doi=10.1016/s0140-6736(98)06423-x|s2cid=25126646}}</ref>
			== See also ==
			* ]
			* ]
			== Notes ==
			{{reflist}}
			== References ==
			* {{Cite journal| last3 = Filley | first1 = G. D. | first2 = N. Z.| last2 = Boctor | first3 = T. R. | first4 = R. M.| last5 = Scott| last4 = Hazen| last7 = Yoder | first5 = J. H. | first6 = A.| last1 = Cody | first7 = H. S. Jr| last6 = Sharma| title = Primordial Carbonylated Iron-Sulfur Compounds and the Synthesis of Pyruvate | journal = Science | volume = 289| issue = 5483 | pages = 1337–1340 | year = 2000| pmid = 10958777 | doi = 10.1126/science.289.5483.1337|bibcode = 2000Sci...289.1337C | s2cid = 14911449 }}
			==External links==
			*
			{{commons}}
			{{Glycolysis}}
			{{Amino acid metabolism intermediates}}
			{{Authority control}}
			{{DEFAULTSORT:Pyruvic Acid}}
			]
			]
			]
			]
			]