2-HYDROXYBUTYRIC ACID

Details

Stereochemistry	RACEMIC
Molecular Formula	C4H8O3
Molecular Weight	104.1045
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(O)C(O)=O

InChI

InChIKey=AFENDNXGAFYKQO-UHFFFAOYSA-N

InChI=1S/C4H8O3/c1-2-3(5)4(6)7/h3,5H,2H2,1H3,(H,6,7)

HIDE SMILES / InChI

Molecular Formula	C4H8O3
Molecular Weight	104.1045
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

PubMed

Title	Date	PubMed
600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances.	1993 Aug	8257730
Potassium concentration differences in the vitreous humour from the two eyes revisited by microanalysis with capillary electrophoresis.	2001 Jul 27	11521901
Inhibition of in vitro CO2 production and lipid synthesis by 2-hydroxybutyric acid in rat brain.	2001 May	11323749
The Na(+)/H(+) exchange inhibitor eniporide as an adjunct to early reperfusion therapy for acute myocardial infarction. Results of the evaluation of the safety and cardioprotective effects of eniporide in acute myocardial infarction (ESCAMI) trial.	2001 Nov 15	11704395
Inhibition and regulation of rat liver L-threonine dehydrogenase by different fatty acids and their derivatives.	2001 Nov 7	11731084
Addition of ester enolates to N-alkyl-2-fluoropyridinium salts: total synthesis of (+/-)-20-deoxycamptothecin and (+)-camptothecin.	2002 Oct 18	12375981
Effect of training duration and exercise on blood-borne substrates, plasma lactate and enzyme concentrations in Andalusian, Anglo-Arabian and Arabian breeds.	2002 Sep	12405695
Effects of N-n-butyl haloperidol iodide on rat myocardial ischemia and reperfusion injury and L-type calcium current.	2003 Aug	12904274
Studies of the brain specificity of S100B and neuron-specific enolase (NSE) in blood serum of acute care patients.	2003 Aug 15	12909297
Evaluation of clinical utility of serum enzymes and troponin-T in the early stages of acute myocardial infarction.	2003 Jul	23105398
Indicators of erythrocyte damage after microwave warming of packed red blood cells.	2003 May	12709371
Electron acquisition system constructed from an NAD-independent D-lactate dehydrogenase and cytochrome c2 in Rhodopseudomonas palustris No. 7.	2004 Mar	15056881
Alpha-hydroxybutyrate dehydrogenase activity in intrahepatic cholestasis of pregnancy.	2005 Jun	15919390
Perturbing the hydrophobic pocket of mandelate racemase to probe phenyl motion during catalysis.	2005 Jun 28	15966725
Urinary endogenous concentrations of GHB and its isomers in healthy humans and diabetics.	2005 May 10	15749359
[Change of myocardial enzymes in patients with acute tetramine poisoning].	2006 Jun	16824338
On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes: selective esterification of simple 2-hydroxycarboxylic acids.	2007	17443833
A unicenter, randomized, double-blind, parallel-group, placebo-controlled study of Melatonin as an Adjunct in patients with acute myocaRdial Infarction undergoing primary Angioplasty The Melatonin Adjunct in the acute myocaRdial Infarction treated with Angioplasty (MARIA) trial: study design and rationale.	2007 Jul	17123867
Biomass in the manufacture of industrial products--the use of proteins and amino acids.	2007 Jun	17387469
Bacillus decisifrondis sp. nov., isolated from soil underlying decaying leaf foliage.	2007 May	17473244
Cytotoxic and Antihaptotactic beauvericin analogues from precursor-directed biosynthesis with the insect pathogen Beauveria bassiana ATCC 7159.	2007 Sep	17803266
Effects of the selective serotonin reuptake inhibitor fluoxetine on counterregulatory responses to hypoglycemia in individuals with type 1 diabetes.	2008 Dec	18835927
[Clinical value of monitoring serum cardiac biomarkers in pulmonary thromboembolism-induced myocardial injury].	2008 Oct	18971188
Clinical applications of urinary organic acids. Part I: Detoxification markers.	2008 Sep	18950247
Effects of intensive therapy and antecedent hypoglycemia on counterregulatory responses to hypoglycemia in type 2 diabetes.	2009 Mar	19073776
Biochemical toxicity of nano-anatase TiO2 particles in mice.	2009 Summer	19066734
Hemolysis is associated with low reticulocyte production index and predicts blood transfusion in severe malarial anemia.	2010 Apr 6	20386613
Consumption of pasteurized human lysozyme transgenic goats' milk alters serum metabolite profile in young pigs.	2010 Aug	19847666
Plasma metabolomic profiles reflective of glucose homeostasis in non-diabetic and type 2 diabetic obese African-American women.	2010 Dec 10	21170321
Quinone-dependent D-lactate dehydrogenase Dld (Cg1027) is essential for growth of Corynebacterium glutamicum on D-lactate.	2010 Dec 15	21159175
Cladielloides A and B: new eunicellin-type diterpenoids from an Indonesian octocoral Cladiella sp.	2010 Dec 6	21339957
Quantitative analysis of gamma-hydroxybutyrate at endogenous concentrations in hair using liquid chromatography tandem mass spectrometry.	2010 Mar 1	20141559
alpha-hydroxybutyrate is an early biomarker of insulin resistance and glucose intolerance in a nondiabetic population.	2010 May 28	20526369
Enantioselective oxidation of 2-hydroxy carboxylic acids by glycolate oxidase and catalase coexpressed in methylotrophic Pichia pastoris.	2010 May-Jun	20014430
Drug off-target effects predicted using structural analysis in the context of a metabolic network model.	2010 Sep 23	20957118
Predictive toxicology using systemic biology and liver microfluidic "on chip" approaches: application to acetaminophen injury.	2012 Mar 15	22230336

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:54:20 GMT 2023` Edited by `admin` on `Sat Dec 16 09:54:20 GMT 2023`
Record UNII	O0ADR0I4H5
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

2-HYDROXYBUTYRIC ACID

Systematic Name

English

(RS)-2-HYDROXYBUTYRIC ACID

Systematic Name

English

NSC-6495

Code

English

BUTANOIC ACID, 2-HYDROXY-, (±)-

Common Name

English

2-HYDROXY-BUTANOIC ACID

Systematic Name

English

DL-2-HYDROXYBUTANOIC ACID

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

621751