Pyruvic acid

Molecular FormulaC₃H₄O₃
Average mass88.062 Da
Monoisotopic mass88.016045 Da
ChemSpider ID1031

More details:

Systematic name
2-Oxopropanoic acid
SMILES
CC(=O)C(=O)O
Std. InChi
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)
Std. InChIKey
LCTONWCANYUPML-UHFFFAOYSA-N
Cite this record
CSID:1031, http://www.chemspider.com/Chemical-Structure.1031.html (accessed 19:14, Dec 9, 2023)

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Names and Synonyms
Database ID(s)

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

127-17-3 [RN]

204-824-3 [EINECS]

2-oxo-Propanoic acid

2-Oxopropanoic acid [ACD/IUPAC Name]

2-Oxopropansäure [German] [ACD/IUPAC Name]

2-OXOPROPIONIC ACID

506211 [Beilstein]

Acide 2-oxopropanoïque [French] [ACD/IUPAC Name]

a-Ketopropionic Acid

Brenztraubensaure [German]

More...

Propanoic acid, 2-oxo- [ACD/Index Name]

Pyroracemic acid

Pyruvic acid [Wiki]

α-keto propionic acid

α-ketopropionic acid

α-Ketopropionic acid

[127-17-3] [RN]

113-24-6 [RN]

143164-46-9 [RN]

1892-67-7 [RN]

2-oxopropanoic acid

2-KETOPROPANOIC ACID

2-ketopropionic acid

2-Oxoglutaric Acid

2-oxopropanoicacid

2-Oxopropansaeure

2-oxo-propinoic acid

2-Oxo-propionic acid

2-Oxopropionsaeure

acetyl formic acid

acetylformic acid

Acid pyruvate

acide pyruvique

AKG

BPV

Brenztraubensaeure

BTS

PROPANOIC ACID, OXO-

PROPOXY, 1,2-DIOXO-

Pyruvic acid, 3-mercapto-

STR00365

α-Ketopropanoic acid

α-ketopropionic acid

α-Oxopropionsaeure

丙酮酸 [Chinese]

Less...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

2970 [DBID]

8558G7RUTR [DBID]

MFCD00002585 [DBID]

UNII-HO43T60JMG [DBID]

UZ0829800 [DBID]

107360_ALDRICH [DBID]

15940_FLUKA [DBID]

AI3-11220 [DBID]

bmse000112 [DBID]

BR-68807 [DBID]

More...

BRN 0506211 [DBID]

C00022 [DBID]

CCRIS 4693 [DBID]

CHEBI:32816 [DBID]

FEMA No. 2970 [DBID]

LMFA01060077 [DBID]

LS-2371 [DBID]

NCGC00165990-01 [DBID]

NChemBio.2007.20-comp11 [DBID]

nchembio867-comp8 [DBID]

NCIOpen2_000039 [DBID]

NSC 179 [DBID]

NSC179 [DBID]

P76209_ALDRICH [DBID]

P-9250 [DBID]

UNII:8558G7RUTR [DBID]

UNII-8558G7RUTR [DBID]

UZ 0829800 [DBID]

W297003_ALDRICH [DBID]

W297070_ALDRICH [DBID]

Less...

Experimental data
Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon
Predicted - Mcule

References
- Fema No:
  
  2970 Sigma-Aldrich ALDRICH-W297003, ALDRICH-W297070

Experimental Physico-chemical Properties

Experimental Melting Point:

11-12 °C Alfa Aesar

12 °C OU Chemical Safety Data (No longer updated) More details

11.8 °C Jean-Claude Bradley Open Melting Point Dataset 16561

13.8 °C Jean-Claude Bradley Open Melting Point Dataset 22302, 28500, 28501, 28502, 28503, 28504

12 °C Jean-Claude Bradley Open Melting Point Dataset 15323, 28500, 28501, 28502, 28503, 28504

11.5 °C Jean-Claude Bradley Open Melting Point Dataset 28500, 28501, 28502, 28503, 28504

11 °C Jean-Claude Bradley Open Melting Point Dataset 8372

11-12 °C Alfa Aesar A13875

11-12 °C Oakwood

11.8 °C Wikidata Q213580

11-12 °C Sigma-Aldrich ALDRICH-107360

11-12 °C Oakwood 168700

Experimental Boiling Point:

164-166 °C Alfa Aesar

164 °C Food and Agriculture Organization of the United Nations 2-Oxopropanoic acid

165 °C (Decomposes) OU Chemical Safety Data (No longer updated) More details

164-166 °C Alfa Aesar A13875

165 °C Oakwood

165 °C Wikidata Q213580

165 °C Sigma-Aldrich ALDRICH-107360

165 °C Oakwood 168700

Experimental Flash Point:

83 °C Alfa Aesar

82 °C OU Chemical Safety Data (No longer updated) More details

83 °C Alfa Aesar

83 °F (28.3333 °C) Alfa Aesar A13875

82 °C Oakwood

82 °C Sigma-Aldrich ALDRICH-107360

82 °C Oakwood 168700

Experimental Refraction Index:

1.428 Alfa Aesar A13875

1.424-1.435 Food and Agriculture Organization of the United Nations 2-Oxopropanoic acid

1.428 Sigma-Aldrich ALDRICH-107360

Experimental Density:

1.267 g/mL Alfa Aesar A13875

1.267 g/mL Oakwood 168700

1.25 g/mL Wikidata Q213580

1.267 g/mL Sigma-Aldrich ALDRICH-107360

Miscellaneous

Appearance:

colourless liquid OU Chemical Safety Data (No longer updated) More details

colourless to amber viscous liquid with a sour vinegar-like odour Food and Agriculture Organization of the United Nations 2-Oxopropanoic acid

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. Refrigerate. OU Chemical Safety Data (No longer updated) More details

Toxicity:

Organic Compound; Drug; Food Toxin; Dietary Supplement; Micronutrient; Metabolite; Nutraceutical; Animal Toxin; Natural Compound; Supplement Toxin, Toxin-Target Database T3D4325

Safety:

20-23-26-36/37/39-45-60 Alfa Aesar A13875

26-36/37/39-45 Alfa Aesar A13875

34 Alfa Aesar A13875

8 Alfa Aesar A13875

Danger Alfa Aesar A13875

DANGER: CORROSIVE, burns skin and eyes Alfa Aesar A13875

H314 Alfa Aesar A13875

P280-P305+P351+P338-P309-P310 Alfa Aesar A13875

Safety glasses, adequate ventilation. OU Chemical Safety Data (No longer updated) More details

A 2-oxo monocarboxylic acid that is the 2-keto derivative of propionic acid. It is a metabolite obtained during glycolysis. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32816, CHEBI:32816

Compound Source:

(R)-lactate + a ubiquinone[inner membrane] -> pyruvate + an ubiquinol[inner membrane] PlantCyc PYRUVATE, PYRUVATE

(S)-lactate[in] + an electron-transfer quinone[membrane] -> pyruvate[in] + an electron-transfer quinol[membrane] PlantCyc PYRUVATE, PYRUVATE

(Z)-phenylmethanethial S-oxide biosynthesis PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

1,4-dihydroxy-2-naphthoate biosynthesis II (plants) PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

4-deoxy-L-threo-hex-4-enopyranuronate degradation PlantCyc PYRUVATE

4-hydroxy-4-methyl-L-glutamate biosynthesis PlantCyc PYRUVATE, PYRUVATE

4-hydroxybenzoate biosynthesis II (microbes) PlantCyc PYRUVATE

acetaldehyde biosynthesis II PlantCyc PYRUVATE, PYRUVATE, PYRUVATE

acridone alkaloid biosynthesis PlantCyc PYRUVATE, PYRUVATE

Aegilops tauschii PlantCyc PYRUVATE

alliin metabolism PlantCyc PYRUVATE

Amaranthus hypochondriacus PlantCyc PYRUVATE

Amborella trichopoda PlantCyc PYRUVATE

an L-cysteine-S-conjugate + H2O = a thiol + pyruvate + ammonium PlantCyc PYRUVATE, PYRUVATE, PYRUVATE

an L-cysteine-S-conjugate + H2O -> a thiol + pyruvate + ammonium PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

an L-cysteine-S-conjugate + H2O -> pyruvate + a thiol + ammonium PlantCyc PYRUVATE, PYRUVATE

Anacardium occidentale PlantCyc PYRUVATE

Ananas comosus PlantCyc PYRUVATE

Aquilegia coerulea PlantCyc PYRUVATE

Arabidopsis halleri PlantCyc PYRUVATE

Arabidopsis lyrata PlantCyc PYRUVATE

Arabidopsis thaliana col PlantCyc PYRUVATE

Asparagus officinalis PlantCyc PYRUVATE

Beta vulgaris subsp. vulgaris PlantCyc PYRUVATE

Boechera stricta PlantCyc PYRUVATE

Brachypodium distachyon PlantCyc PYRUVATE

Brassica napus PlantCyc PYRUVATE

Brassica oleracea var. capitata PlantCyc PYRUVATE

Brassica oleracea var. oleracea PlantCyc PYRUVATE

Brassica rapa FPsc PlantCyc PYRUVATE

Brassica rapa subsp. pekinensis PlantCyc PYRUVATE

C4 photosynthetic carbon assimilation cycle, NAD-ME type PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

C4 photosynthetic carbon assimilation cycle, NADP-ME type PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

C4 photosynthetic carbon assimilation cycle, PEPCK type PlantCyc PYRUVATE, PYRUVATE

Calotropis gigantea PlantCyc PYRUVATE

Camptotheca acuminata PlantCyc PYRUVATE

Cannabis sativa PlantCyc PYRUVATE

Capsella grandiflora PlantCyc PYRUVATE

Capsella rubella PlantCyc PYRUVATE

Capsicum annuum PlantCyc PYRUVATE

Carica papaya PlantCyc PYRUVATE

Catharanthus roseus PlantCyc PYRUVATE

Chenopodium quinoa PlantCyc PYRUVATE

Chlamydomonas reinhardtii PlantCyc PYRUVATE

Chromochloris zofingiensis PlantCyc PYRUVATE

Cicer arietinum PlantCyc PYRUVATE

Citrus clementina PlantCyc PYRUVATE

Citrus sinensis PlantCyc PYRUVATE

Coccomyxa subellipsoidea C-169 PlantCyc PYRUVATE

Corchorus capsularis PlantCyc PYRUVATE

Cucumis sativus PlantCyc PYRUVATE

Daucus carota subsp. sativus PlantCyc PYRUVATE

Dianthus caryophyllus PlantCyc PYRUVATE

Dioscorea rotundata PlantCyc PYRUVATE

ephedrine biosynthesis PlantCyc PYRUVATE

ethiin metabolism PlantCyc PYRUVATE

Eucalyptus grandis PlantCyc PYRUVATE

Eutrema salsugineum PlantCyc PYRUVATE

Fragaria vesca subsp. vesca PlantCyc PYRUVATE

gamma-coniciene and coniine biosynthesis PlantCyc PYRUVATE

gluconeogenesis III PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

glutathione-mediated detoxification II PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

Glycine max PlantCyc PYRUVATE

glycolysis II (from fructose 6-phosphate) PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

Gossypium raimondii PlantCyc PYRUVATE

Helianthus annuus PlantCyc PYRUVATE

Hordeum vulgare subsp. vulgare PlantCyc PYRUVATE

Humulus lupulus var. lupulus PlantCyc PYRUVATE

hypoglycin biosynthesis PlantCyc PYRUVATE, PYRUVATE

indole-3-acetate biosynthesis II PlantCyc PYRUVATE, PYRUVATE, PYRUVATE

Kalanchoe fedtschenkoi PlantCyc PYRUVATE

Kalanchoe laxiflora PlantCyc PYRUVATE

L-cysteate + H2O = sulfite + pyruvate + ammonium + H+ PlantCyc PYRUVATE, PYRUVATE

L-cysteine + H2O -> pyruvate + ammonium + hydrogen sulfide PlantCyc PYRUVATE

L-cysteine + H2O -> pyruvate + hydrogen sulfide + ammonium PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

L-cysteine degradation II PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

Leersia perrieri PlantCyc PYRUVATE

Linum usitatissimum PlantCyc PYRUVATE

L-lysine biosynthesis I PlantCyc PYRUVATE

Lotus japonicus PlantCyc PYRUVATE

L-phenylalanine degradation III PlantCyc PYRUVATE, PYRUVATE

L-tryptophan + H2O -> indole + pyruvate + ammonium PlantCyc PYRUVATE

lupanine biosynthesis PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

Malus domestica PlantCyc PYRUVATE

Manihot esculenta PlantCyc PYRUVATE

Marchantia polymorpha PlantCyc PYRUVATE

Medicago truncatula PlantCyc PYRUVATE

methiin metabolism PlantCyc PYRUVATE

methylglyoxal degradation I PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

Micromonas commoda RCC299 PlantCyc PYRUVATE

Micromonas pusilla CCMP1545 PlantCyc PYRUVATE

Mimulus guttatus PlantCyc PYRUVATE

Miscanthus sinensis PlantCyc PYRUVATE

Musa acuminata PlantCyc PYRUVATE

Nicotiana tabacum PlantCyc PYRUVATE

Olea europaea var. sylvestris PlantCyc PYRUVATE

Oropetium thomaeum PlantCyc PYRUVATE

Oryza brachyantha PlantCyc PYRUVATE

Oryza glaberrima PlantCyc PYRUVATE

Oryza punctata PlantCyc PYRUVATE

Oryza rufipogon PlantCyc PYRUVATE

Oryza sativa Japonica Group PlantCyc PYRUVATE

Ostreococcus lucimarinus PlantCyc PYRUVATE

Panicum hallii PlantCyc PYRUVATE

Panicum virgatum PlantCyc PYRUVATE

Petunia axillaris PlantCyc PYRUVATE

Phaseolus vulgaris PlantCyc PYRUVATE

phosphoenolpyruvate + an [HPr]-L-histidine -> pyruvate + an [HPr protein]-Npi-phospho-L-histidine PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

Physcomitrella patens PlantCyc PYRUVATE

Populus trichocarpa PlantCyc PYRUVATE

propanethial S-oxide biosynthesis PlantCyc PYRUVATE

Prunus persica PlantCyc PYRUVATE

pyruvate + coenzyme A + NAD+ -> acetyl-CoA + CO2 + NADH PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

pyruvate fermentation to acetate IV PlantCyc PYRUVATE, PYRUVATE

pyruvate fermentation to acetate VII PlantCyc PYRUVATE

pyruvate fermentation to acetoin III PlantCyc PYRUVATE, PYRUVATE

pyruvate fermentation to ethanol I PlantCyc PYRUVATE, PYRUVATE

reductive monocarboxylic acid cycle PlantCyc PYRUVATE

reductive TCA cycle I PlantCyc PYRUVATE, PYRUVATE

Ricinus communis PlantCyc PYRUVATE

Rosa chinensis PlantCyc PYRUVATE

Rosa multiflora PlantCyc PYRUVATE

S-(hercyn-2-yl)-L-cysteine S-oxide + a reduced electron acceptor -> ergothioneine + pyruvate + ammonium + an oxidized electron acceptor PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

salicylate biosynthesis I PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

Salvia miltiorrhiza PlantCyc PYRUVATE

Selaginella moellendorffii PlantCyc PYRUVATE

serinol biosynthesis PlantCyc PYRUVATE

Setaria italica PlantCyc PYRUVATE

Setaria viridis PlantCyc PYRUVATE

Solanum lycopersicum PlantCyc PYRUVATE

Solanum melongena PlantCyc PYRUVATE

Solanum pennellii PlantCyc PYRUVATE

Solanum tuberosum PlantCyc PYRUVATE

Sorghum bicolor PlantCyc PYRUVATE

Sphagnum fallax PlantCyc PYRUVATE

Spinacia oleracea PlantCyc PYRUVATE

Spirodela polyrhiza PlantCyc PYRUVATE

superpathway of fermentation (Chlamydomonas reinhardtii) PlantCyc PYRUVATE, PYRUVATE

TCA cycle variation V (plant) PlantCyc PYRUVATE, PYRUVATE

tetrahydrofolate biosynthesis II PlantCyc PYRUVATE, PYRUVATE

Thellungiella parvula PlantCyc PYRUVATE

Theobroma cacao PlantCyc PYRUVATE

Trifolium pratense PlantCyc PYRUVATE

Triticum aestivum PlantCyc PYRUVATE

Triticum urartu PlantCyc PYRUVATE

Vitis vinifera PlantCyc PYRUVATE

Volvox carteri PlantCyc PYRUVATE

Zea mays subsp. mays PlantCyc PYRUVATE

Zostera marina PlantCyc PYRUVATE

Bio Activity:

(R)-lactate + a ubiquinone[inner membrane] -> pyruvate + an ubiquinol[inner membrane] PlantCyc PYRUVATE, PYRUVATE

(R)-lactate + NAD+ <- pyruvate + NADH + H+ PlantCyc PYRUVATE

(R)-lactate[in] + a ubiquinone[membrane] -> pyruvate[in] + an ubiquinol[membrane] PlantCyc PYRUVATE, PYRUVATE, PYRUVATE

(S)-lactate + NAD+ <--> pyruvate + NADH + H+ PlantCyc PYRUVATE, PYRUVATE

(S)-malate + (S)-malate + NAD+ + NAD+ -> pyruvate + CO2 + CO2 + pyruvate + NADH + NADH PlantCyc PYRUVATE

(S)-malate + NAD+ -> CO2 + pyruvate + NADH PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

2 pyruvate -> 4-hydroxy-4-methyl-2-oxoglutarate PlantCyc PYRUVATE, PYRUVATE

2-aminoprop-2-enoate + H2O -> pyruvate + ammonium PlantCyc PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE, PYRUVATE

2-dehydro-3-deoxy-D-gluconate 6-phosphate -> D-glyceraldehyde 3-phosphate + pyruvate PlantCyc PYRUVATE

2-iminopropanoate + H2O -> pyruvate + ammonium PlantCyc PYRUVATE, PYRUVATE,