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Pyruvic acid

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(Redirected fromPyruvate)
Simplest of the alpha-keto acids
Pyruvic acid
Names
Preferred IUPAC name
2-Oxopropanoic acid[1]
Systematic IUPAC name
2-Oxopropionic acid
Other names
Pyruvic acid[1]
α-Ketopropionic acid
Acetylformic acid
Pyroracemic acid
Acetylcarboxylic acid
Identifiers
3D model (JSmol)
AbbreviationsPyr
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.004.387Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6) checkY
    Key: LCTONWCANYUPML-UHFFFAOYSA-N checkY
  • O=C(C(=O)O)C
Properties
C3H4O3
Molar mass88.06 g/mol
Density1.250 g/cm3
Melting point11.8 °C (53.2 °F; 284.9 K)
Boiling point165 °C (329 °F; 438 K)
Acidity (pKa)2.50[2]
Related compounds
Otheranions
Pyruvate

Related compounds
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Pyruvic acid (CH3COCOOH) is the simplest of thealpha-keto acids, with acarboxylic acid and aketone functional group.Pyruvate, theconjugate base, CH3COCOO, is anintermediate in severalmetabolic pathways throughout the cell.

Pyruvic acid can be made fromglucose throughglycolysis, converted back tocarbohydrates (such as glucose) viagluconeogenesis, or converted tofatty acids through a reaction withacetyl-CoA.[3] It can also be used to construct the amino acidalanine and can be converted intoethanol orlactic acid viafermentation.

Pyruvic acid supplies energy tocells through thecitric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternativelyferments to producelactate when oxygen is lacking.[4]

Chemistry

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In 1834,Théophile-Jules Pelouze distilledtartaric acid and isolatedglutaric acid and another unknown organic acid.Jöns Jacob Berzelius characterized this other acid the following year and named pyruvic acid because it was distilled using heat.[5][6] The correct molecular structure was deduced by the 1870s.[7]

Pyruvic acid is a colorless liquid with a smell similar to that ofacetic acid and ismiscible with water.[8] In the laboratory, pyruvic acid may be prepared by heating a mixture oftartaric acid andpotassium hydrogen sulfate,[9] by theoxidation ofpropylene glycol by a strong oxidizer (e.g.,potassium permanganate orbleach), or by the hydrolysis ofacetyl cyanide, formed by reaction ofacetyl chloride withpotassium cyanide:[citation needed]

CH3COCl + KCN → CH3COCN + KCl
CH3COCN → CH3COCOOH

Biochemistry

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Pyruvate is an importantchemical compound inbiochemistry. It is the output of the metabolism ofglucose known asglycolysis.[10] One molecule ofglucose breaks down into two molecules of pyruvate,[10] which are then used to provide further energy, in one of two ways. Pyruvate is converted intoacetyl-coenzyme A, which is the main input for a series of reactions known as theKrebs cycle (also known as the citric acid cycle or tricarboxylic acid cycle). Pyruvate is also converted tooxaloacetate by ananaplerotic reaction, which replenishes Krebs cycle intermediates; also, the oxaloacetate is used forgluconeogenesis.[citation needed]

These reactions are named afterHans Adolf Krebs, the biochemist awarded the 1953Nobel Prize for physiology, jointly withFritz Lipmann, for research into metabolic processes. The cycle is also known as thecitric acid cycle or tricarboxylic acid cycle, because citric acid is one of the intermediate compounds formed during the reactions.[citation needed]

If insufficient oxygen is available, the acid is broken downanaerobically, creatinglactate in animals andethanol in plants and microorganisms (and incarp[11]). Pyruvate from glycolysis is converted byfermentation tolactate using theenzymelactate dehydrogenase and thecoenzymeNADH in lactatefermentation, or toacetaldehyde (with the enzymepyruvate decarboxylase) and then toethanol inalcoholic fermentation.[citation needed]

Pyruvate is a key intersection in the network ofmetabolic pathways. Pyruvate can be converted intocarbohydrates viagluconeogenesis, tofatty acids or energy throughacetyl-CoA, to theamino acidalanine, and toethanol. Therefore, it unites several key metabolic processes.[citation needed]

Reference ranges for blood tests, comparing blood content of pyruvate (shown in violet near middle) with other constituents.

Pyruvic acid production by glycolysis

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In the last step ofglycolysis,phosphoenolpyruvate (PEP) is converted to pyruvate bypyruvate kinase. This reaction is strongly exergonic and irreversible; ingluconeogenesis, it takes two enzymes,pyruvate carboxylase andPEP carboxykinase, to catalyze the reverse transformation of pyruvate to PEP.[citation needed]

phosphoenolpyruvatepyruvate kinasepyruvic acid
 
ADPATP
ADPATP
 
 pyruvate carboxylase andPEP carboxykinase

CompoundC00074 atKEGG Pathway Database.Enzyme2.7.1.40 atKEGG Pathway Database.CompoundC00022 atKEGG Pathway Database.

Click on genes, proteins and metabolites below to link to respective articles.[§ 1]

  1. ^The interactive pathway map can be edited at WikiPathways:"GlycolysisGluconeogenesis_WP534".

Decarboxylation to acetyl CoA

[edit]

Pyruvate decarboxylation by thepyruvate dehydrogenase complex producesacetyl-CoA.

pyruvatepyruvate dehydrogenase complexacetyl-CoA
 
CoA+ NAD+CO2+ NADH+ H+


Carboxylation to oxaloacetate

[edit]

Carboxylation bypyruvate carboxylase producesoxaloacetate.

pyruvatepyruvate carboxylaseoxaloacetate
 
ATP+ CO2ADP+ Pi


Transamination to alanine

[edit]

Transamination byalanine transaminase producesalanine.

pyruvatealanine transaminasealanine
 
glutamateα-ketoglutarate
glutamateα-ketoglutarate


Reduction to lactate

[edit]

Reduction bylactate dehydrogenase produceslactate.

pyruvatelactate dehydrogenaselactate
 
NADHNAD+
NADHNAD+


Environmental chemistry

[edit]

Pyruvic acid is an abundant carboxylic acid insecondary organic aerosols.[12]

Uses

[edit]

Pyruvate is sold as aweight-loss supplement, though credible science has yet to back this claim. Asystematic review of sixtrials found a statistically significant difference in body weight with pyruvate compared toplacebo. However, all of the trials had methodological weaknesses and the magnitude of the effect was small. The review also identifiedadverse events associated with pyruvate such as diarrhea, bloating, gas, and increase inlow-density lipoprotein (LDL) cholesterol. The authors concluded that there was insufficient evidence to support the use of pyruvate for weight loss.[13]

There is alsoin vitro as well asin vivo evidence in hearts that pyruvate improves metabolism byNADH production stimulation and increases cardiac function.[14][15]

See also

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Notes

[edit]
  1. ^abNomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge:The Royal Society of Chemistry. 2014. p. 748.doi:10.1039/9781849733069-FP001.ISBN 978-0-85404-182-4.
  2. ^Dawson, R. M. C.; et al. (1959).Data for Biochemical Research. Oxford: Clarendon Press.
  3. ^Fox, Stuart Ira (2011).Human Physiology (12th ed.). McGraw=Hill. p. 146.[ISBN missing]
  4. ^Ophardt, Charles E."Pyruvic Acid - Cross Roads Compound".Virtual Chembook. Elmhurst College. Archived fromthe original on July 31, 2018. RetrievedApril 7, 2017.
  5. ^Thomson, Thomas (1838)."Chapter II. Of fixed acids Section".Chemistry of organic bodies, vegetables. London: J. B. Baillière. p. 65. RetrievedDecember 1, 2010.
  6. ^Berzelius, J. (1835)."Ueber eine neue, durch Destillation von Wein-und Traubensäure erhaltene Säure".Annalen der Pharmacie.13 (1):61–63.doi:10.1002/jlac.18350130109.
  7. ^"Pyruvic acid".Journal of the Chemical Society, Abstracts.34: 31. 1878.doi:10.1039/CA8783400019.
  8. ^"Pyruvic Acid".ChemSpider. Royal Society of Chemistry. Retrieved21 April 2017.
  9. ^Howard, J. W.; Fraser, W. A."Pyruvic Acid".Organic Syntheses.4: 63;Collected Volumes, vol. 1, p. 475.
  10. ^abLehninger, 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.
  11. ^Aren van Waarde; G. Van den Thillart;Maria Verhagen (1993). "Ethanol Formation and pH-Regulation in Fish".Surviving Hypoxia. CRC Press. pp. 157–170.hdl:11370/3196a88e-a978-4293-8f6f-cd6876d8c428.ISBN 0-8493-4226-0.
  12. ^Guzman, Marcelo I.; Eugene, Alexis J. (2021-09-01)."Aqueous Photochemistry of 2-Oxocarboxylic Acids: Evidence, Mechanisms, and Atmospheric Impact".Molecules.26 (17): 5278.doi:10.3390/molecules26175278.PMC 8433822.PMID 34500711.
  13. ^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.doi:10.1080/10408398.2011.565890.PMID 24188231.S2CID 20241217.
  14. ^Jaimes, R. III (Jul 2015)."Functional response of the isolated, perfused normoxic heart to pyruvate dehydrogenase activation by dichloroacetate and pyruvate".Pflügers Arch.468 (1):131–42.doi:10.1007/s00424-015-1717-1.PMC 4701640.PMID 26142699.
  15. ^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.doi:10.1016/s0140-6736(98)06423-x.ISSN 0140-6736.PMID 10218531.S2CID 25126646.

References

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External links

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Wikimedia Commons has media related toPyruvic acid.
Kacetyl-CoA
lysine
leucine
tryptophanalanine
G
G→pyruvate
citrate
glycine
serine
G→glutamate
α-ketoglutarate
histidine
proline
arginine
other
G→propionyl-CoA
succinyl-CoA
valine
isoleucine
methionine
threonine
propionyl-CoA
G→fumarate
phenylalaninetyrosine
G→oxaloacetate
Other
Cysteine metabolism
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