Pyruvic Acid

Title: Pyruvic Acid
CAS Registry Number: 127-17-3
CAS Name: 2-Oxopropanoic acid
Additional Names: a-ketopropionic acid; acetylformic acid; pyroracemic acid; brenztraubensäure (German)
Molecular Formula: C3H4O3
Molecular Weight: 88.06
Percent Composition: C 40.92%, H 4.58%, O 54.51%
Line Formula: CH3COCOOH
Literature References: Intermediate in sugar metabolism and in enzymatic carbohydrate degradation (alcoholic fermentation) where it is converted to acetaldehyde and CO2 by carboxylase, see Nord, Chem. Rev. 26, 423 (1940). In muscle, pyruvic acid (derived from glycogen) is reduced to lactic acid during exertion, which is reoxidized and partially retransformed to glycogen during rest. The liver can convert pyruvic acid to alanine by amination. Pyruvic acid has been isolated from cane sugar fermentation broth by fixation with b-naphthylamine giving a-methyl-b-naphthocinchonic acid: Grab, Biochem. Z. 123, 84 (1921). The most practical method of preparing pyruvic acid is by distillation of tartaric acid in presence of potassium acid sulfate as dehydrating agent. The distillate must be fractionated under reduced pressure: Erlenmeyer, Ber. 14, 321 (1881); Döbner, Ann. 242, 269 (1887); Howard, Fraser, Org. Synth. coll. vol. I (2nd ed., 1941) p 475.
Properties: Liquid. Odor resembling that of acetic acid. d415 1.267; mp 11.8°; bp760 165° (dec); bp100 106.5°; bp40 85.3°; bp20 70.8°; bp10 57.9°; bp5 45.8°; bp1.0 21.4°; nD20 1.4138. Absorption spectrum: Henri, Fromageot, Bull. Soc. Chim. [4] 37, 846 (1925). pK (25°) 2.49. Miscible with water, alcohol, ether. Polymerizes and dec on standing unless pure and kept in container with airtight closure.
Melting point: mp 11.8°
Boiling point: bp760 165° (dec); bp100 106.5°; bp40 85.3°; bp20 70.8°; bp10 57.9°; bp5 45.8°; bp1.0 21.4°
pKa: pK (25°) 2.49
Index of refraction: nD20 1.4138
Density: d415 1.267
Derivative Type: Methyl ester
Molecular Formula: C4H6O3
Molecular Weight: 102.09
Percent Composition: C 47.06%, H 5.92%, O 47.02%
Properties: Liquid, bp760 134-137°.
Boiling point: bp760 134-137°
Derivative Type: Ethyl ester
Molecular Formula: C5H8O3
Molecular Weight: 116.12
Percent Composition: C 51.72%, H 6.94%, O 41.33%
Properties: Liquid, bp760 155°; bp750 147.5°; bp42 69-71°; bp20 66° also 56°. Prepn from ethyl lactate by oxidation with KMnO4: Cornforth, Org. Synth. coll. vol. IV, 467 (1963).
Boiling point: bp760 155°; bp750 147.5°; bp42 69-71°; bp20 66° also 56°
Pyrvinium Pamoate Q-Enzyme Quantum Dye Quassin Quatrimycin

Pyruvic acid
Pyruvic-acid-2D-skeletal.png Pyruvic-acid-3D-balls.png
Identifiers
CAS number 127-17-3 YesY
PubChem 1060
ChemSpider 1031 YesY
UNII 8558G7RUTR YesY
DrugBank DB00119
KEGG C00022 N
ChEBI CHEBI:32816 YesY
ChEMBL CHEMBL1162144 YesY
Jmol-3D images Image 1
Properties
Molecular 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[1]
Related compounds
Other anions pyruvate ion
ion of pyruvic acid
   Pyruvate-3D-balls.png
Related keto-acids, carboxylic acids acetic acid
glyoxylic acid
oxalic acid
propionic acid
acetoacetic acid
Related compounds propionaldehyde
glyceraldehyde
methylglyoxal
sodium pyruvate
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Pyruvic acid (CH3COCOOH) is an organic acid, a ketone, as well as the simplest of the alpha-keto acids. The carboxylate (COO) anion of pyruvic acid, its Brønsted–Lowry conjugate base, CH3COCOO, is known as pyruvate, and is a key intersection 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 acetyl-CoA. It can also be used to construct the amino acid alanine and be converted into ethanol.

Pyruvic acid supplies energy to living cells through the citric acid cycle (also known as the Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactic acid when oxygen is lacking (fermentation).