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

Approval Year

PubMed

Title	Date	PubMed
Clinical conditions associated with urinary excretion of 2-hydroxybutyric acid.	1975 May	168632
600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances.	1993 Aug	8257730
Crystallization and some properties of D-lactate dehydrogenase from Staphylococcus sp. LDH-1.	2002	16233312
[Changes of myocardial enzymes in patients with acute carbon monoxide poisoning].	2003 Feb	14761575
Evaluation of clinical utility of serum enzymes and troponin-T in the early stages of acute myocardial infarction.	2003 Jul	23105398
The effects of inhaled nitric oxide on cardiac pathology and energy metabolism in a canine model of smoke inhalation injury.	2004 Feb	14693088
Electron acquisition system constructed from an NAD-independent D-lactate dehydrogenase and cytochrome c2 in Rhodopseudomonas palustris No. 7.	2004 Mar	15056881
[Changes in myocardial enzyme spectrum and electrocardiogram after Salmonella food poisoning].	2004 Nov	15567791
[Specific features of the laboratory diagnosis of myocardial infarction in patients with anemia].	2005 Dec	16498949
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
[Protective effects of urinastatin on organ function in patients with severe burn].	2006 Jan	16464386
[Change of myocardial enzymes in patients with acute tetramine poisoning].	2006 Jun	16824338
Differential myolysis of myocardium and skeletal muscle in hamsters with dilated cardiomyopathy: beneficial protective effect of diltiazem.	2006 Nov	17062977
Analysis of polyploid cells in mouse embryonic cells cultured under diabetic conditions.	2006 Sep	16922922
On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes: selective esterification of simple 2-hydroxycarboxylic acids.	2007	17443833
Effects of dexrazoxane and amifostine on evolution of Doxorubicin cardiomyopathy in vivo.	2007 Dec	18040065
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
Metabolic characterisation of plasma in juveniles with glycogen storage disease type 1a (GSD1a) by high-resolution (1)H NMR spectroscopy.	2007 Jun	17149801
Bacillus decisifrondis sp. nov., isolated from soil underlying decaying leaf foliage.	2007 May	17473244
Qualitative analysis of products formed during the acid catalyzed liquefaction of bagasse in ethylene glycol.	2007 May	17157499
Cytotoxic and Antihaptotactic beauvericin analogues from precursor-directed biosynthesis with the insect pathogen Beauveria bassiana ATCC 7159.	2007 Sep	17803266
Potential hepatoprotective effects of fullerenol C60(OH)24 in doxorubicin-induced hepatotoxicity in rats with mammary carcinomas.	2008 Aug-Sep	18501960
[Effect of intensive insulin treatment on cardiac myocytes of severely scalded rats].	2008 Dec	19111118
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 a selective serotonin reuptake inhibitor, fluoxetine, on counterregulatory responses to hypoglycemia in healthy individuals.	2008 Sep	18567822
Acute doxorubicin nephrotoxicity in rats with malignant neoplasm can be successfully treated with fullerenol C60(OH)24 via suppression of oxidative stress.	2008 Sep-Oct	19066422
Hematology and serum chemistry parameters in juvenile cynomolgus monkeys (Macaca fascicularis) of Mauritius origin: comparison between purpose-bred and captured animals.	2009 Aug	19236562
Comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry for metabonomics: Biomarker discovery for diabetes mellitus.	2009 Feb 9	19166731
Effects of intensive therapy and antecedent hypoglycemia on counterregulatory responses to hypoglycemia in type 2 diabetes.	2009 Mar	19073776
Metabonomic phenotype and identification of "heart blood stasis obstruction pattern" and "qi and yin deficiency pattern" of myocardial ischemia rat models.	2009 Nov	19937207
Two D-2-hydroxy-acid dehydrogenases in Arabidopsis thaliana with catalytic capacities to participate in the last reactions of the methylglyoxal and beta-oxidation pathways.	2009 Sep 11	19586914
Biochemical toxicity of nano-anatase TiO2 particles in mice.	2009 Summer	19066734
The VP1-unique region of parvovirus B19 induces myocardial injury in mice.	2010	19883162
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
(1)H NMR-based metabonomic investigation of the effect of two different exercise sessions on the metabolic fingerprint of human urine.	2010 Dec 3	20932058
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
Multi-parameter detection of diabetes mellitus on multichannel poly(dimethylsiloxane) analytical chips coupled with nanoband microelectrode arrays.	2010 Sep	20725918
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

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