Pyruvic acid
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| General | ||||||||||||||||||||||
| Surname | Pyruvic acid | |||||||||||||||||||||
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| Molecular formula | C 3 H 4 O 3 | |||||||||||||||||||||
| Brief description |
after acetic acid smelling, colorless liquid |
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| properties | ||||||||||||||||||||||
| Molar mass | 88.06 g mol −1 | |||||||||||||||||||||
| Physical state |
liquid |
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| density |
1.27 g cm −3 |
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| Melting point |
12 ° C |
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| boiling point |
Decomposes at 165 ° C |
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| pK s value |
2.49 |
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| solubility |
miscible with water |
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| Refractive index |
1.4280 (20 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C | ||||||||||||||||||||||
Pyruvic acid , also called acetylformic acid , is the simplest of the keto carboxylic acids . Their salts and esters are called pyruvates . In biochemistry , pyruvate is the anion of pyruvic acid and is a C-3 body. The pyruvic acid molecule has an α- carbonyl group . The acyl residue (CH 3 COCO–) of pyruvic acid is called pyruvoyl .
presentation
The name pyruvic acid is derived from the first production: tartaric acid was subjected to dry distillation (what was then known as pyruvic acid ); this creates pyruvic acid after decarboxylation and splitting off of water. In English the compound is called pyruvic acid , derived from the Greek pyr (fire, heat) and the Latin uva (grape, especially grape).
Jöns Jakob Berzelius represented pyruvic acid around 1835 by jointing tartaric acid with potassium hydrogen sulfate.
properties
The flash point of the colorless liquid, which can be mixed with any water, is 82 ° C.
Biochemical significance
The anion of pyruvic acid, pyruvate , is an important intermediate product in aerobic and anaerobic metabolism .
It arises, for example, in the cytoplasm of a cell when glucose is phosphorylated and broken down twice in the context of glycolysis .
proof
The analytical detection can be carried out with phenylhydrazine , α- or β-naphthol or 2,4-dinitrophenylhydrazine .
use
By reaction with a boiling solution of barium hydroxide can 5-methylisophthalic acid are obtained. Methyl pyruvate is produced by reaction with methanol in the presence of p-toluenesulfonic acid .
Individual evidence
- ↑ Entry on PYRUVIC ACID in the CosIng database of the EU Commission, accessed on May 22, 2020.
- ↑ a b Entry on pyruvic acid. In: Römpp Online . Georg Thieme Verlag, accessed on May 25, 2014.
- ↑ a b c d e f Entry for CAS no. 127-17-3 in the GESTIS substance database of the IFA , accessed on April 25, 2016(JavaScript required) .
- ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-452.
- ↑ Entry on pyruvic acid in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.
- ↑ Dihydric Alcohols, Their Oxidation Products and Derivatives: A Modern Comprehensive Treatise . Elsevier, 2016, ISBN 978-1-4832-2131-1 , pp. 232 ( books.google.de ).
- ↑ Google Patents: CN105646208A - Preparation method of methyl pyruvate - Google Patents , accessed December 15, 2018
- ^ A. Weissberger and CJ Kibler: METHYL PYRUVATE. In: Organic Syntheses. 24, 1944, p. 72, doi : 10.15227 / orgsyn.024.0072 .
literature
- Michael T. Madigan, John M. Martinko, Michael Thomm (Eds.): Brock Microbiology . Pearson Studies; 11. revised Edition, 2006, ISBN 3-8273-7187-2 .
- Jeremy M. Berg, Lubert Stryer and John L. Tymoczko: Biochemistry , Spectrum Akademischer Verlag GmbH Heidelberg; 6th edition, 2003, ISBN 3-8274-1800-3 .
