WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/06/11 12:26:27」(JST)

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Pyruvic acid (CH₃COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate base, CH₃COCOO⁻, 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.^[3] 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).^[4]

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^[5]) and another acid that Jöns Jacob Berzelius characterized the following year and named pyruvic acid.^[6] Pyruvic acid is a colorless liquid with a smell similar to that of acetic acid and is miscible with water.^[7] In the laboratory, pyruvic acid may be prepared by heating a mixture of tartaric acid and potassium hydrogen sulfate,^[8] 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:

CH₃COCl + KCN → CH₃COCN + KCl

CH₃COCN → CH₃COCOOH

Biochemistry

Pyruvate is an important chemical compound in biochemistry. It is the output of the metabolism of glucose known as glycolysis.^[9] One molecule of glucose breaks down into two molecules of pyruvate,^[9] 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^[10]). 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. ^{[§ 1]}

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|{{{bSize}}}px|alt=Glycolysis and Gluconeogenesis edit]]

File:WP534.png

Glycolysis and Gluconeogenesis edit

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

Decarboxylation to acetyl CoA

Pyruvate decarboxylation by the pyruvate dehydrogenase complex produces acetyl-CoA.

pyruvate	pyruvate dehydrogenase complex		acetyl-CoA

	CoA + NAD⁺	CO₂ + NADH + H⁺

Carboxylation to oxaloacetate

Carboxylation by pyruvate carboxylase produces oxaloacetate.

pyruvate	pyruvate carboxylase		oxaloacetate

	ATP + CO₂	ADP + P_i

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.^[11]

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.^[12]^[13]

Notes

^ ^a ^b 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.
^ Dawson, R. M. C.; et al. (1959). Data for Biochemical Research. Oxford: Clarendon Press.
^ Fox, Stuart Ira (2011). Human Physiology (12th ed.). McGraw=Hill. p. 146. ^{[ISBN missing]}
^ Ophardt, Charles E. "Pyruvic Acid - Cross Roads Compound". Virtual Chembook. Elmhurst College. Retrieved April 7, 2017.
^ Thomson, Thomas (1838). "Chapter II. Of fixed acids Section". Chemistry of organic bodies, vegetables. London: J. B. Baillière. p. 65. Retrieved December 1, 2010.
^ Thorpe, Thomas Edward (1922). "Glutaric acid". A dictionary of applied chemistry. 3. London: Longmans, Green, and Co. pp. 426–427. Retrieved December 1, 2010.
^ "Pyruvic Acid". ChemSpider. Royal Society of Chemistry. Retrieved 21 April 2017.
^ Howard, J. W.; Fraser, W. A. "Pyruvic Acid". Org. Synth. 4: 63. ; Coll. Vol., 1, p. 475
^ ^a ^b 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.
^ 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.
^ 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.
^ 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.
^ 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...289.1337C. PMID 10958777. doi:10.1126/science.289.5483.1337.

External links

Pyruvic acid mass spectrum

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 先天性代謝異常：個々の障害の発見 inborn errors of metabolism identifying the specific disorder
2. ピルビン酸キナーゼ欠損症 pyruvate kinase deficiency
3. Causes of hypoglycemia in infants and children
4. 先天性代謝異常：代謝性救急疾患 inborn errors of metabolism metabolic emergencies
5. 遺伝性運動失調の概要 overview of the hereditary ataxias

English Journal

The chemistry of sour taste and the strategy to reduce the sour taste of beer.

Li H1, Liu F2.
Food chemistry.Food Chem.2015 Oct 15;185:200-4. doi: 10.1016/j.foodchem.2015.03.135. Epub 2015 Apr 4.
The contributions of free hydrogen ions, undissociated hydrogen ions in protonated acid species, and anionic acid species to sour taste were studied through sensory experiments. According to tasting results, it can be inferred that the basic substance producing a sour taste is the hydrogen ion, incl
PMID 25952858

The ipdC, hisC1 and hisC2 genes involved in indole-3-acetic production used as alternative phylogenetic markers in Azospirillum brasilense.

Jijón-Moreno S1, Marcos-Jiménez C, Pedraza RO, Ramírez-Mata A, de Salamone IG, Fernández-Scavino A, Vásquez-Hernández CA, Soto-Urzúa L, Baca BE.
Antonie van Leeuwenhoek.Antonie Van Leeuwenhoek.2015 Jun;107(6):1501-17. doi: 10.1007/s10482-015-0444-0. Epub 2015 Apr 5.
Plant growth-promoting bacteria of the genus Azospirillum are present in the rhizosphere and as endophytes of many crops. In this research we studied 40 Azospirillum strains isolated from different plants and geographic regions. They were first characterized by 16S rDNA restriction analysis, and the
PMID 25842039

Using [1-(13) C]lactic acid for hyperpolarized (13) C MR cardiac studies.

Chen AP1, Lau JY2,3, Alvares RD4, Cunningham CH2,3.
Magnetic resonance in medicine.Magn Reson Med.2015 Jun;73(6):2087-93. doi: 10.1002/mrm.25354. Epub 2014 Jul 9.
PURPOSE: Hyperpolarized [1-(13) C]lactate in solution may be a clinically relevant and safe substrate for real time MR investigations of key metabolic pathways. The potential of using hyperpolarized [1-(13) C]lactate for magnetic resonance studies of cardiac metabolism in vivo was explored.METHODS:
PMID 25046652

Japanese Journal

Acidithiobacillus ferrooxidans を生体触媒として利用した大気CO_2からの細胞外ピルビン酸製造

石居拓己,中川広崇,橋本和仁,中村龍平
電気化学および工業物理化学 : denki kagaku 80(5), 327-329, 2012-05-05
NAID 10030143766

血糖,尿糖,血中・尿中ケトン体,血中乳酸,血中ピルビン酸 (最新臨床糖尿病学(上)糖尿病学の最新動向) -- (糖尿病の検査・診断法)

清水一紀,石川恵理,福田哲也 [他]
日本臨床 70(-) (1020(増刊3)), 433-437, 2012-05
NAID 40019324281

Related Pictures

★リンクテーブル★

リンク元	「ピルビン酸」「pyruvate」
拡張検索	「4-hydroxyphenylpyruvic acid dioxygenase deficiencies」「phenylpyruvic acid」「4-hydroxyphenylpyruvic acid」「phosphoenlpyruvic acid」

「ピルビン酸」

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	C3H4O3
Molar mass	88.06 g/mol
Density	1.250 g/cm3
Melting point	11.8 °C (53.2 °F; 284.9 K)
Boiling point	165 °C (329 °F; 438 K)
Acidity (pKa)	2.50
Related compounds
Other anions	pyruvate ion; ion of pyruvic acid
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).
	verify (what is ?)
	Infobox references

　　[★]

英: pyruvate, pyruvic acid, 2-oxopropanic acid, α-ketopropionic acid
同: 焦性ブドウ酸 pyroracemic acid
関: 解糖系

α-ケト酸である。

CH₃-CO-COOH

CoAとピルビン酸デヒドロゲナーゼにより、脱炭酸し、アセチルCoA(CH₃-CO-CoA)となる。