File:Pyruvic-acid-2D-skeletal.svg · Wikimedia Commons · See Wikimedia Commons
pyruvic acid
Sign in to saveAlso known as pyruvate, alpha-ketopropionic acid, 2-ketopropionic acid, acetylformic acid, CH3COCOOH, a-Ketopropionic acid, 2-Oxopropionate, Pyroracemate
simplest of the alpha-keto acids
OverviewAI-generated
Pyruvic acid, also identified by the IUPAC name 2-oxopropanoic acid, is a chemical compound with the formula C₃H₄O₃. It has a molecular weight of 88.06 and a canonical SMILES notation of CC(=O)C(=O)O. The substance possesses a pKa of 2.50 and a charge of 0.
Physical properties include a melting point of 11.8 and a boiling point of 165. The density is listed as 1.25. Computational descriptors indicate an xlogp of -0.3 and a topological polar surface area of 54.4. The molecule contains one hydrogen bond donor and three hydrogen bond acceptors.
Pyruvic acid is the subject of 11,879 entries in the PubMed literature database. It is also referenced by 875 other encyclopedia articles.
Synthesized by Vinony from 22 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C3H4O3
- Molecular weight
- 88.06 g/mol
- IUPAC name
- 2-oxopropanoic acid
- SMILES
- CC(=O)C(=O)O
- InChIKey
- LCTONWCANYUPML-UHFFFAOYSA-N
- XLogP
- -0.3
- Polar surface area
- 54.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
11,879 papers- Enteric coronavirus PDCoV evokes a non-Warburg effect by hijacking pyruvic acid as a metabolic hub.Redox biology · 2024Su G, Liu J, Duan C et al.DOI: 10.1016/j.redox.2024.103112
- Pyruvic acid prevents Cu(2+)/Zn(2+)-induced neurotoxicity by suppressing mitochondrial injury.Biochemical and biophysical research communications · 2018Tanaka KI, Shimoda M, Kawahara MDOI: 10.1016/j.bbrc.2017.11.152
- Biotechnological production of pyruvic acid.ReviewApplied microbiology and biotechnology · 2001Li Y, Chen J, Lun SYDOI: 10.1007/s002530100804
- Production of pyruvic acid from glycerol by Yarrowia lipolytica.Folia microbiologica · 2019Cybulski K, Tomaszewska-Hetman L, Rakicka M et al.DOI: 10.1007/s12223-019-00695-2
- Pyruvic acid stress caused color attenuation by interfering with anthocyanins metabolism during alcoholic fermentation.Food chemistry · 2022Li X, Teng Z, Luo Z et al.DOI: 10.1016/j.foodchem.2021.131251
- [Pyruvic acid].Nihon rinsho. Japanese journal of clinical medicine · 2004Taminato T
- Simultaneous determination of lactic acid and pyruvic acid in tissue and cell culture media by gas chromatography after in situ derivatization-ultrasound-assisted emulsification microextraction.Analytical and bioanalytical chemistry · 2019Zhang HY, Tan XX, Kang K et al.DOI: 10.1007/s00216-018-1502-z
- Enhancement of pyruvic acid production in Candida glabrata by engineering hypoxia-inducible factor 1.Bioresource technology · 2020Luo Z, Zeng W, Du G et al.DOI: 10.1016/j.biortech.2019.122248
via PubMed
~8 min read
Encyclopedic overview
Names
Preferred IUPAC name 2-Oxopropanoic acid
Excerpted from Wikipedia’s “pyruvic acid” article, available under the CC BY-SA 4.0 licence.