ACETOACETIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H6O3
Molecular Weight	102.0886
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)CC(O)=O

InChI

InChIKey=WDJHALXBUFZDSR-UHFFFAOYSA-N

InChI=1S/C4H6O3/c1-3(5)2-4(6)7/h2H2,1H3,(H,6,7)

HIDE SMILES / InChI

Molecular Formula	C4H6O3
Molecular Weight	102.0886
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
The loop between helix 4 and helix 5 in the monocarboxylate transporter MCT1 is important for substrate selection and protein stability.	2003-12-01	12946269
Investigation of conserved acidic residues in 3-hydroxy-3-methylglutaryl-CoA lyase: implications for human disease and for functional roles in a family of related proteins.	2003-09-26	12874287
Redox pacing of proteome turnover: influences of glutathione and ketonemia.	2003-09-15	12941300
Hibernation impact on the catalytic activities of the mitochondrial D-3-hydroxybutyrate dehydrogenase in liver and brain tissues of jerboa (Jaculus orientalis).	2003-09-10	12964952
Use of some novel alternative electron sinks to inhibit ruminal methanogenesis.	2003-09-06	12956318
Differential influences of peroxisome proliferator-activated receptors gamma and -alpha on food intake and energy homeostasis.	2003-09	12941763
Fatal overdose of the herbicide bentazone.	2003-08-27	12927403
Spectrophotometric and fluorimetric determination of hexamine in pure form and its pharmaceutical formulation.	2003-08	12913281
Perspectives on the metabolic management of epilepsy through dietary reduction of glucose and elevation of ketone bodies.	2003-08	12859666
Pitfalls in the measurement of some intermediary metabolites.	2003-07	12880533
Luminal fermentation and colonocyte metabolism in a rat model of enteral nutrition.	2003-07	12870792
Elevated blood interleukin-6 levels in hyperketonemic type 1 diabetic patients and secretion by acetoacetate-treated cultured U937 monocytes.	2003-07	12832326
Repeated bouts of high-intensity exercise and muscle glycogen sparing in the rat.	2003-07	12771165
Reduced SOD activity and increased neural tube defects in embryos of the sensitive but not of the resistant Cohen diabetic rats cultured under diabetic conditions.	2003-06	12962287
The relationship between free and total calcium concentrations in the matrix of liver and brain mitochondria.	2003-05-23	12660243
On the mammalian acetone metabolism: from chemistry to clinical implications.	2003-05-02	12726989
Ketone bodies disturb fatty acid handling in isolated cardiomyocytes derived from control and diabetic rats.	2003-05-01	12489982
A novel pyrroline-5-carboxylic acid and acetoacetic acid adduct in hyperprolinaemia type II.	2003-05	12691858
An automatic flow procedure for the determination of 3-hydroxybutyrate in animal serum and plasma.	2003-04-23	12696920
Effect of a monensin controlled release capsule on metabolic parameters in transition dairy cows.	2003-04	12741541
Osmotonicity of acetoacetate: possible implications for cerebral edema in diabetic ketoacidosis.	2003-04	12709664
Evaluation of diabetic ketoacidosis-related ionic metabolites in human blood serum by capillary electrophoresis.	2003-04	12707913
High performance liquid chromatographic determination of acetoacetate by post-column derivatization with p-nitrobenzene diazonium fluoroborate.	2003-04	12673014
Acetoacetate augments beta-adrenergic inotropism of stunned myocardium by an antioxidant mechanism.	2003-04	12595283
Expression of acetoacetyl-CoA synthetase, a novel cytosolic ketone body-utilizing enzyme, in human brain.	2003-03-15	12623130
Distinct effects of ketone bodies on down-regulation of cell surface insulin receptor and insulin receptor substrate-1 phosphorylation in adrenal chromaffin cells.	2003-03	12604674
High beta-hydroxybutyrate concentration in liver and skeletal muscle of newly hatched chicks.	2003-03	12600671
Influence of age and caloric restriction on liver glycolytic enzyme activities and metabolite concentrations in mice.	2003-03	12581789
Simultaneous measurement of plasma concentrations and 13C-enrichment of short-chain fatty acids, lactic acid and ketone bodies by gas chromatography coupled to mass spectrometry.	2003-02-05	12505787
Time empty and ketone body status in the early postpartum period of dairy cows.	2003-02	12535328
Chloride present in biological samples as a tool for enhancement of sensitivity in capillary zone electrophoretic analysis of anionic trace analytes.	2003-01	12569541
Acetoacetate protects hippocampal neurons against glutamate-mediated neuronal damage during glycolysis inhibition.	2003	12890508
Acetoacetate increases expression of intercellular adhesion molecule-1 (ICAM-1) in human brain microvascular endothelial cells.	2002-12-13	12435474
Structure of the mammalian CoA transferase from pig heart.	2002-12-10	12463743
Design of the pH profile for asymmetric bioreduction of ethyl 4-chloro-3-oxobutyrate on the basis of a data-driven method.	2002-12-07	12467479
Complex I-mediated reactive oxygen species generation: modulation by cytochrome c and NAD(P)+ oxidation-reduction state.	2002-12-01	12180906
dl-3-Hydroxybutyrate administration prevents myocardial damage after coronary occlusion in rat hearts.	2002-11	12384475
Transport of ketone bodies and lactate in the sheep ruminal epithelium by monocarboxylate transporter 1.	2002-11	12381528
Structural basis for CO2 fixation by a novel member of the disulfide oxidoreductase family of enzymes, 2-ketopropyl-coenzyme M oxidoreductase/carboxylase.	2002-10-29	12390015
Effects of hypothermia on myocardial substrate selection.	2002-10	12400770
Polyunsaturated fatty acids and acetoacetate downregulate the expression of the ATP-binding cassette transporter A1.	2002-10	12351428
A decarboxylase encoded at the Cochliobolus heterostrophus translocation-associated Tox1B locus is required for polyketide (T-toxin) biosynthesis and high virulence on T-cytoplasm maize.	2002-09	12236595
Crystallization and preliminary X-ray analysis of an R-2-hydroxypropyl-coenzyme M dehydrogenase.	2002-09	12198305
The succinate mechanism of insulin release.	2002-09	12196457
Epilepsy and the ketogenic diet: assessment of ketosis in children using breath acetone.	2002-09	12193682
[Blood level of ketone bodies and its clinical significance].	2002-08	12355785
Effects of a non-starch polysaccharidase enzyme preparation from Thermomyces lanuginosus on energy and protein metabolism and milk yield of dairy cattle.	2002	12498145
Relationship between concentration of citrate and ketone bodies in cow's milk.	2002	12237966
Evaluation of an automated method of percent reactive antibody determination.	1992-11	1293081
The oxidation of citramalic acid and beta-hydroxyglutaric acid to acetoacetic acid and the possible significance of citramalic acid in plant metabolism.	1954-05	13160012

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:56 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:56 GMT 2025`
Record UNII	4ZI204Y1MC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETOACETIC ACID [MI]

Preferred Name

English

ACETOACETIC ACID

Systematic Name

English

.ALPHA.-KETOBUTYRATE

Systematic Name

English

3-OXOBUTYRIC ACID

Systematic Name

English

3-KETOBUTYRATE

Systematic Name

English

BUTANOIC ACID, 3-OXO-

Common Name

English

Code System Code Type Description

SMS_ID

100000165775