2-hydroxybutyric acid
butyric acid, 2-hydroxy- (8CI)
 
Notes:
2-Hydroxybutyric acid is an organic acid that is involved in propanoate metabolism. It is produced in mammalian tissues (principaly hepatic) that catabolize L-threonine or synthesize glutathione. Oxidative stress or detoxification demands can dramatically increase the rate of hepatic glutathione synthesis. Under such metabolic stress conditions, supplies of L-cysteine for glutathione synthesis become limiting, so homocysteine is diverted from the transmethylation pathway forming methionine into the transsulfuration pathway forming cystathionine. 2-Hydroxybutyrate is released as a by-product when cystathionine is cleaved to cysteine that is incorporated into glutathione. 2-Hydroxybutyric acid is often found in the urine of patients suffering from lactic acidosis and ketoacidosis. 2-Hydroxybutyric acid generally appears at high concentrations in situations related to deficient energy metabolism (e.g., birth asphyxia) and also in inherited metabolic diseases affecting the central nervous system during neonatal development, such as "cerebral" lactic acidosis, glutaric aciduria type II, dihydrolipoyl dehydrogenase (E3) deficiency, and propionic acidemia. More recently it has been noted that elevated levels of alpha-hydroxybutyrate in the plasma is a good marker for early stage type II diabetes (PMID: 19166731). It was concluded from studies done in the mid 1970's that an increased NADH2/NAD ratio was the most important factor for the production of 2-hydorxybutyric acid (PMID: 168632) [HMDB]
Synonyms   Articles   Notes   Search
CAS Number: 565-70-8Picture of molecule3D/inchi
Nikkaji Web: J130.629D
Beilstein Number: 878248
XlogP3-AA: 0.10 (est)
Molecular Weight: 104.10536000
Formula: C4 H8 O3
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
Synonyms   Articles   Notes   Search   Top
Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 44.00 °C. @ 760.00 mm Hg
Boiling Point: 260.00 °C. @ 760.00 mm Hg
Boiling Point: 238.00 to  239.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.008000 mmHg @ 25.00 °C. (est)
Flash Point: 234.00 °F. TCC ( 112.20 °C. ) (est)
logP (o/w): -0.341 (est)
Soluble in:
 water, 1e+006 mg/L @ 25 °C (est)
Synonyms   Articles   Notes   Search   Top
Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
Synonyms   Articles   Notes   Search   Top
Cosmetic Information:
None found
Synonyms   Articles   Notes   Search   Top
Suppliers:
 None found
Synonyms   Articles   Notes   Search   Top
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Synonyms   Articles   Notes   Search   Top
Safety in Use Information:
Category: natural substances and extractives
Recommendation for 2-hydroxybutyric acid usage levels up to:
 not for fragrance use.
 
Recommendation for 2-hydroxybutyric acid flavor usage levels up to:
 not for flavor use.
Synonyms   Articles   Notes   Search   Top
Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 11266
National Institute of Allergy and Infectious Diseases: Data
 2-hydroxybutanoic acid
Chemidplus: 0000565708
Synonyms   Articles   Notes   Search   Top
References:
 2-hydroxybutanoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 11266
Pubchem (sid): 134978444
Synonyms   Articles   Notes   Search   Top
Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
KEGG (GenomeNet): C05984
HMDB (The Human Metabolome Database): HMDB00008
FooDB: FDB021867
YMDB (Yeast Metabolome Database): YMDB00441
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
Synonyms   Articles   Notes   Search   Top
Potential Blenders and core components note
 
None Found
 
Synonyms   Articles   Notes   Search   Top
Potential Uses:
None Found
Synonyms   Articles   Notes   Search   Top
Occurrence (nature, food, other): note
 found in nature
Synonyms   Articles   Notes   Search   Top
Synonyms:
 butanoic acid, 2-hydroxy-
 butanoic acid, 2-hydroxy- (9CI)
 butyric acid, 2-hydroxy- (8CI)
2-hydroxy-DL-butyric acid
2-hydroxy-N-butyric acid
a-hydroxy-N-butyric acid
alpha-hydroxy-N-butyric acid
DL-2-hydroxy-N-butyric acid
2-hydroxybutanoic acid
a-hydroxybutanoic acid
DL-2-hydroxybutanoic acid
a-hydroxybutyric acid
alpha-hydroxybutyric acid
DL-2-hydroxybutyric acid
DL-a-hydroxybutyric acid
Synonyms   Articles   Notes   Search   Top
Articles:
PubMed: Metabolomics study of hepatocellular carcinoma: discovery and validation of serum potential biomarkers by using capillary electrophoresis-mass spectrometry.
PubMed: Exploring metabolic syndrome serum profiling based on gas chromatography mass spectrometry and random forest models.
PubMed: Draft Genome Sequence of the Gluconobacter oxydans Strain DSM 2003, an Important Biocatalyst for Industrial Use.
PubMed: GC-MS analysis of blood for the metabonomic investigation of the effects of physical exercise and allopurinol administration on rats.
PubMed: One-pot microbial production, mechanical properties, and enzymatic degradation of isotactic P[(R)-2-hydroxybutyrate] and its copolymer with (R)-lactate.
PubMed: "Prediction is very hard, especially about the future": new biomarkers for type 2 diabetes?
PubMed: A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease.
PubMed: Early metabolic markers of the development of dysglycemia and type 2 diabetes and their physiological significance.
PubMed: A novel serum metabolomics-based diagnostic approach for colorectal cancer.
PubMed: Response to weaning and dietary L-glutamine supplementation: metabolomic analysis in piglets by gas chromatography/mass spectrometry.
PubMed: Prospective study of changes in the metabolomic profiles of men during their first three months of androgen deprivation therapy for prostate cancer.
PubMed: Efficient conversion of 1,2-butanediol to (R)-2-hydroxybutyric acid using whole cells of Gluconobacter oxydans.
PubMed: Biosynthesis of polyhydroxyalkanoates containing 2-hydroxybutyrate from unrelated carbon source by metabolically engineered Escherichia coli.
PubMed: [Exometabolites of some anaerobic microorganisms of human microflora].
PubMed: Kinetic resolution of 2-hydroxybutanoate racemic mixtures by NAD-independent L-lactate dehydrogenase.
PubMed: (1)H NMR-based metabonomic investigation of the effect of two different exercise sessions on the metabolic fingerprint of human urine.
PubMed: alpha-hydroxybutyrate is an early biomarker of insulin resistance and glucose intolerance in a nondiabetic population.
PubMed: Enantioselective oxidation of 2-hydroxy carboxylic acids by glycolate oxidase and catalase coexpressed in methylotrophic Pichia pastoris.
PubMed: Comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry for metabonomics: Biomarker discovery for diabetes mellitus.
PubMed: Clinical applications of urinary organic acids. Part I: Detoxification markers.
PubMed: Proton HR-MAS NMR spectroscopic characterization of metabolites in various human organ tissues: pancreas, brain and liver from trauma cases.
PubMed: On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes: selective esterification of simple 2-hydroxycarboxylic acids.
PubMed: Metabolic characterisation of plasma in juveniles with glycogen storage disease type 1a (GSD1a) by high-resolution (1)H NMR spectroscopy.
PubMed: Direct sample injection for capillary electrophoretic determination of organic acids in cerebrospinal fluid.
PubMed: Analysis of polyploid cells in mouse embryonic cells cultured under diabetic conditions.
PubMed: Evidence for distinct L-methionine catabolic pathways in the yeast Geotrichum candidum and the bacterium Brevibacterium linens.
PubMed: Perturbing the hydrophobic pocket of mandelate racemase to probe phenyl motion during catalysis.
PubMed: Oxidative activation of the human carcinogen chromate by arsenite: a model for synergistic metal activation leading to oxidative DNA damage.
PubMed: Synthesis of all four stereoisomers of 3-amino-2-hydroxybutanoic acids.
PubMed: Catabolism of volatile sulfur compounds precursors by Brevibacterium linens and Geotrichum candidum, two microorganisms of the cheese ecosystem.
PubMed: Biosynthesis of (2R)-4-amino-2-hydroxybutyric acid, unique and biologically significant substituent in butirosins.
PubMed: Determination of valproic acid (2-propylpentanoic acid) in human plasma by capillary electrophoresis with indirect UV detection.
PubMed: Solid-phase synthesis of endothelin receptor antagonists.
PubMed: Addition of ester enolates to N-alkyl-2-fluoropyridinium salts: total synthesis of (+/-)-20-deoxycamptothecin and (+)-camptothecin.
PubMed: Improved narrowband dipolar recoupling for homonuclear distance measurements in rotating solids.
PubMed: Directed biosynthesis of new enniatins.
PubMed: Inhibition and regulation of rat liver L-threonine dehydrogenase by different fatty acids and their derivatives.
PubMed: Inhibition of in vitro CO2 production and lipid synthesis by 2-hydroxybutyric acid in rat brain.
PubMed: Configurational analysis of chiral acids as O-trifluoroacetylated (-)-menthyl esters by achiral dual-capillary column gas chromatography.
PubMed: Enantiomeric separation and discrimination of 2-hydroxy acids as O-trifluoroacetylated (S)-(+)-3-methyl-2-butyl esters by achiral dual-capillary column gas chromatography.
PubMed: Which organic acids does hemofiltrate contain in the presence of acute renal failure?
PubMed: [Comparative analysis of changes in respiration and systemic hemodynamics during activation of GABA receptors in cats and rats].
PubMed: [Methionine malabsorption syndrome].
PubMed: Conversion of DL-threonine, D-threonine and 2-oxobutyrate into propionate and 2-hydroxybutyrate by Fusobacterium species.
PubMed: Blood-brain barrier permeability of glucose and ketone bodies during short-term starvation in humans.
PubMed: Inhibition of citrate oxidation in vitro by 2-hydroxybutyrate and 4-hydroxybutyrate in cerebral cortex of young rats.
PubMed: 2-Hydroxybutyrate and 4-hydroxybutyrate inhibit CO2 formation from labeled substrates by rat cerebral cortex.
PubMed: Involvement of liver in the decompensation of hemorrhagic shock.
PubMed: Production of activated species of oxygen during the chromate(VI)-ascorbate reaction: implication in carcinogenesis.
PubMed: Facile synthesis of chiral 2-hydroxy acids catalyzed by a stable duck epsilon-crystallin with endogenous L-lactate dehydrogenase activity.
PubMed: Effects of birth asphyxia on urinary organic acid excretion.
PubMed: From the Food and Drug Administration.
PubMed: Orally potent human renin inhibitors derived from angiotensinogen transition state: design, synthesis, and mode of interaction.
PubMed: Importance of blood glucose concentration in regulating lipolysis during fasting in humans.
PubMed: D-lactate dehydrogenase. Substrate specificity and use as a catalyst in the synthesis of homochiral 2-hydroxy acids.
PubMed: Epinephrine's effect on metabolic rate is independent of changes in plasma insulin or glucagon.
PubMed: Effects of interrupted insulin treatment on fetal outcome of pregnant diabetic rats.
PubMed: Ketoacid production in acute respiratory and metabolic acidosis and alkalosis in rats.
PubMed: Underfeeding and the physiological responses to infused epinephrine in lean women.
PubMed: The urine osmolal gap: a clue to estimate urine ammonium in "hybrid" types of metabolic acidosis.
PubMed: Resting energy expenditure and food-induced thermogenesis in diabetic children receiving continuous subcutaneous insulin infusion.
PubMed: Effects of alpha-ketobutyrate and alpha-hydroxybutyrate on the enzymatic determination of acetoacetate and beta-hydroxybutyrate.
PubMed: Identification of alpha-hydroxybutyrate in rabbit serum after ethanol ingestion.
PubMed: Biotinidase deficiency: metabolites in CSF.
PubMed: Frequency-pulsed electron capture gas-liquid chromatographic analysis of metabolites produced by Clostridium difficile in broth enriched with amino acids.
PubMed: Studies of urinary organic acid profiles of a patient with dihydrolipoyl dehydrogenase deficiency.
PubMed: Impaired counterregulation of hypoglycemia in insulin-dependent diabetes mellitus.
PubMed: Ischemic change of organic acids in kidney.
PubMed: 1-N-acylation of gentamicin C1a by a cyclic, chiral gamma-amino-alpha-hydroxy acid related to the (S)-4-amino-2-hydroxybutyric acid.
PubMed: Possible DA agonist properties of naloxone.
PubMed: Fetal fuels. V. Ketone bodies inhibit pyrimidine biosynthesis in fetal rat brain.
PubMed: Energy source for secretion in gastric glands.
PubMed: [Non-steroidal anti-inflammatory agents. VIII. 3-(4-biphenyly)-2-hydroxybutyric acid].
PubMed: Synthesis of 5''-amino-3,5''-dideoxybutirosin A.
PubMed: The absolute configuration of urinary 2-hydroxybutyric acid in patients with ketosis and lactic acidosis.
PubMed: Identification of 2-hydroxybutyric acid in human amniotic fluid.
PubMed: The performance of the 'CentrifiChem' parallel fast analyser using packaged reagents.
PubMed: Clinical conditions associated with urinary excretion of 2-hydroxybutyric acid.
PubMed: The formation of 2-hydroxybutyric acid in experimental animals.
PubMed: The occurrence of 2-hydroxybutyric acid in urine from patients with lactic acidosis.
PubMed: Determination of 2-acetolactic acid and 2-aceto-2-hydroxybutyric acid in a fermented solution by gas chromatography.
Synonyms   Articles   Notes   Search   Top
Please share your Comments.
Email Address:
 
 
 
 
Top of Page Home
Copyright © 1980-2020 Perflavory ™ Disclaimer Privacy Policy