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2D Structure
Also known as: 2-oxopropanoic acid, 127-17-3, Acetylformic acid, Pyroracemic acid, 2-oxopropionic acid, Alpha-ketopropionic acid
Molecular Formula
C3H4O3
Molecular Weight
88.06  g/mol
InChI Key
LCTONWCANYUPML-UHFFFAOYSA-N
FDA UNII
8558G7RUTR

An intermediate compound in the metabolism of carbohydrates, proteins, and fats. In thiamine deficiency, its oxidation is retarded and it accumulates in the tissues, especially in nervous structures. (From Stedman, 26th ed)
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-oxopropanoic acid
2.1.2 InChI
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
2.1.3 InChI Key
LCTONWCANYUPML-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
8558G7RUTR
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Pyruvic

2. Pyruvate

2.3.2 Depositor-Supplied Synonyms

1. 2-oxopropanoic Acid

2. 127-17-3

3. Acetylformic Acid

4. Pyroracemic Acid

5. 2-oxopropionic Acid

6. Alpha-ketopropionic Acid

7. 2-ketopropionic Acid

8. Propanoic Acid, 2-oxo-

9. 2-oxopropanoate

10. 2-oxo-propionic Acid

11. 2-oxopropansaeure

12. 2-oxopropionsaeure

13. Alpha-oxopropionsaeure

14. Pyruvic Acid (natural)

15. Acide Pyruvique

16. A-ketopropionic Acid

17. Propanoic Acid, Oxo-

18. Ch3cocooh

19. Fema No. 2970

20. Alpha-keto Propionic Acid

21. Nsc 179

22. .alpha.-ketopropionic Acid

23. 2-ketopropanoic Acid

24. Ai3-11220

25. 8558g7rutr

26. Chebi:32816

27. Nsc-179

28. Dsstox_cid_1650

29. 2-oxo-propanoic Acid

30. Dsstox_rid_76263

31. Dsstox_gsid_21650

32. Pyruvicacid

33. Brenztraubensaeure

34. Cas-127-17-3

35. Pyruvic Acid (8ci)

36. Einecs 204-824-3

37. Brn 0506211

38. Unii-8558g7rutr

39. Acetylformate

40. Pyroracemate

41. A-ketopropionate

42. 2-oxopropionate

43. Acetyl Formic Acid

44. 2-oxopropanoicacid

45. Alpha-ketopropionate

46. 2-oxopropanoic'acid

47. Mfcd00002585

48. Nchembio867-comp8

49. 2-oxo Propanoic Acid

50. Pyruvic Acid, 95%

51. Pyruvic Acid, 98%

52. 4b5s

53. Bmse000112

54. Pyruvic Acid [mi]

55. Pyruvic-2-[13c] Acid

56. P-9250

57. Nciopen2_000039

58. Pyruvic Acid [fhfi]

59. Pyruvic Acid [inci]

60. 4-03-00-01505 (beilstein Handbook Reference)

61. Pyruvic Acid, P.a., 98%

62. Pyruvic Acid [who-dd]

63. Pyruvic Acid, >=97%, Fg

64. Gtpl4809

65. Nsc179

66. Chembl1162144

67. Dtxsid2021650

68. Bdbm19473

69. Pyruvic Acid, Natural, >=80%

70. Amy6082

71. Propanoic Acid, 2-oxo- (9ci)

72. Hy-y0781

73. Zinc1532517

74. Tox21_202096

75. Tox21_303284

76. Bbl027390

77. Lmfa01060077

78. S3143

79. 2-oxopropanoic Acid, Pyroracemic Acid

80. Akos000118803

81. Cs-w020190

82. Db00119

83. Ncgc00165990-01

84. Ncgc00165990-02

85. Ncgc00257000-01

86. Ncgc00259645-01

87. Pyruvic Acid, Technical, >=95.0% (t)

88. Ft-0612738

89. P0579

90. C00022

91. Q213580

92. B3cff0ad-2f35-484c-b062-4ac88a1b2830

93. F2191-0254

94. Z1741977082

95. Pyruvic Acid, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 88.06 g/mol
Molecular Formula C3H4O3
XLogP3-0.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass88.016043985 g/mol
Monoisotopic Mass88.016043985 g/mol
Topological Polar Surface Area54.4 Ų
Heavy Atom Count6
Formal Charge0
Complexity84
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For nutritional supplementation, also for treating dietary shortage or imbalance


5 Pharmacology and Biochemistry
5.1 Pharmacology

Pyruvic acid or pyruvate is a key intermediate in the glycolytic and pyruvate dehydrogenase pathways, which are involved in biological energy production. Pyruvate is widely found in living organisms. It is not an essential nutrient since it can be synthesized in the cells of the body. Certain fruits and vegetables are rich in pyruvate. For example, an average-size red apple contains approximately 450 milligrams. Dark beer and red wine are also rich sources of pyruvate. Recent research suggests that pyruvate in high concentrations may have a role in cardiovascular therapy, as an inotropic agent. Supplements of this dietary substance may also have bariatric and ergogenic applications.


5.2 Absorption, Distribution and Excretion

Absorption

Pyruvate is absorbed from the gastrointestinal tract from whence it is transported to the liver via the portal circulation.


5.3 Metabolism/Metabolites

In the liver, pyruvate is metabolized via several pathways.


5.4 Mechanism of Action

Pyruvate serves as a biological fuel by being converted to acetyl coenzyme A, which enters the tricarboxylic acid or Krebs cycle where it is metabolized to produce ATP aerobically. Energy can also be obtained anaerobically from pyruvate via its conversion to lactate. Pyruvate injections or perfusions increase contractile function of hearts when metabolizing glucose or fatty acids. This inotropic effect is striking in hearts stunned by ischemia/reperfusion. The inotropic effect of pyruvate requires intracoronary infusion. Among possible mechanisms for this effect are increased generation of ATP and an increase in ATP phosphorylation potential. Another is activation of pyruvate dehydrogenase, promoting its own oxidation by inhibiting pyruvate dehydrogenase kinase. Pyruvate dehydrogenase is inactivated in ischemia myocardium. Yet another is reduction of cytosolic inorganic phosphate concentration. Pyruvate, as an antioxidant, is known to scavenge such reactive oxygen species as hydrogen peroxide and lipid peroxides. Indirectly, supraphysiological levels of pyruvate may increase cellular reduced glutathione.