600-15-7

Basic information

• Product Name: DL-2-HYDROXY-N-BUTYRIC ACID
• Synonyms: dl-2-hydroxy-n-butyricacid(alpha-)(containspolymolecular);(±)-2-hydroxybutyric acid;DL-2-Hydroxybutyric Acid (contains Polymolecular esterification product);rac-(2R*)-2-Hydroxybutyric acid;(contains PolyMolecular esterification product);DL-2-Hydroxybutyric Acid DL-alpha-Hydroxybutyric acid;NSC 6495
• CAS NO: 600-15-7
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.1
• EINECS: 209-985-3
• Mol File: 600-15-7.mol
• Article Data: 34

Chemical Properties

• Melting Point: 44 °C
• Boiling Point: 260 °C
• Flash Point: 112.2 °C
• Appearance: /
• Density: 1.1250
• Refractive Index: 1.4298 (589.3 nm 20℃)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: pK1:3.65 (30°C)
• Merck: 14,4816
• CAS DataBase Reference: DL-2-HYDROXY-N-BUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2-HYDROXY-N-BUTYRIC ACID(600-15-7)
• EPA Substance Registry System: DL-2-HYDROXY-N-BUTYRIC ACID(600-15-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-36/37/39-39
• Hazardous Substances Data: 600-15-7(Hazardous Substances Data)

Usage

Description

2-Hydroxybutyric acid (or alpha - hydroxy butyrate) is a hydroxy butyric acid with the hydroxyl group on the carbon adjacent to the carboxyl. It is a chiral compound having two enantiomers, D-2- hydroxybutyric acid and L-2-hydroxybutyric acid. 2-Hydroxy butyrate, the conjugate base of 2-hydroxy butyric acid, is produced in mammalian tissues (principally 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 byproduct when cystathionine is cleaved to cysteine that is incorporated into glutathione. Chronic shifts in the rate of glutathione synthesis may be reflected by urinary excretion of 2-hydroxybutyrate.

Uses

2-Hydroxybutanoic Acid is an analyte used in the diagnoses of colorectal cancer as well as Type II diabetes. It is also used in the purification of the major Vibrio autoinducer and the study of its role in virulence factor production for cholera.

Definition

ChEBI: A hydroxybutyric acid having a single hydroxyl group located at position 2; urinary secretion of 2-hydroxybutyric acid is increased with alcohol ingestion or vigorous physical exercise and is associated with lactic acidosis and ketoacidosis in humans and d abetes in animals.

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

Upstream product

• 86943-35-3 (+/-)-2-hydroxybutanal 
• 26735-70-6 2-hydroxy-2-ethylmalonic acid 
• 533-68-6 2-bromobutyric acid ethyl ester 
• 2443-40-5 trans-2,3-epoxybutanoic acid 
• 584-03-2 1,2-dihydroxybutane 
• 123-72-8 butyraldehyde 
• 7732-18-5 water 
• 5077-67-8 1-Hydroxy-2-butanone 
• 7647-01-0 hydrogenchloride 
• 29263-83-0 diethyl 2-chloro-2-ethylmalonate 
• 80-58-0 2-Bromobutyric acid 
• 7664-93-9 sulfuric acid 
• 67-64-1 acetone 
• 81608-88-0 3-chlorobutyraldehyde 

Downstream Products

• 123-38-6 propionaldehyde 
• 106942-24-9 2-hydroxy-N-phenylpentanamide 
• 3347-90-8 (2S)-2-hydroxybutanoic acid 
• 64-18-6 formic acid 
• 802294-64-0 propionic acid 
• 64-19-7 acetic acid 
• 107-92-6 butyric acid 
• 71-43-2 benzene 
• 600-18-0 2-Oxobutyric acid 
• 584-03-2 1,2-dihydroxybutane 
• 4374-57-6 3,6-diethyl-1,4-dioxane-2,5-dione 
• 1346701-98-1 2-hydroxy-1-(2-phenyl-6,7-dihydro-4H-oxazolo[5,4-c]pyridin-5-yl)-butan-1-one 
• 144-62-7 oxalic acid 
• 15719-64-9 methylammonium carbonate 

Relevant articles and documents

Synthesis of Dicarboxylic Acids from Aqueous Solutions of Diols with Hydrogen Evolution Catalyzed by an Iridium Complex

A catalytic system for the synthesis of dicarboxylic acids from aqueous solutions of diols accompanied by the evolution of hydrogen was developed. An iridium complex bearing a functional bipyridonate ligand with N,N-dimethylamino substituents exhibited a high catalytic performance for this type of dehydrogenative reaction. For example, adipic acid was synthesized from an aqueous solution of 1,6-hexanediol in 97 % yield accompanied by the evolution of four equivalents of hydrogen by the present catalytic system. It should be noted that the simultaneous production of industrially important dicarboxylic acids and hydrogen, which is useful as an energy carrier, was achieved. In addition, the selective dehydrogenative oxidation of vicinal diols to give α-hydroxycarboxylic acids was also accomplished.

Antioxidant Properties of Heterocyclic Intermediates of the Maillard Reaction and Structurally Related Compounds

It is well established that a wide range of reductones is formed in the course of the Maillard reaction and that these substances contribute to the oxidative stability of food. The aim of this study was to analyze 12 important heterocyclic intermediates with and without reductone structure as well as structurally related substances under equal conditions to compare their antioxidant properties in detail. For this purpose, five methods were selected including photometrical methods such as the trolox equivalent antioxidant capacity assay and an electron paramagnetic resonance spectroscopic method. Reductones with furan-3-one structure and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one were reducing in all assays, whereas isomaltol and maltol did not react in assays based on the reduction of metal ions because of their complexing abilities. The introduction of protecting groups to the free hydroxyl functions of selected reductones could nearly eliminate their reducing abilities. In addition, the oxidation products of the different reductive heterocycles were compared after treatment with iodine. Mainly short-chained organic acids such as lactic, glycolic, and glyceric acid are formed as result of the degradation, which indicates 1,3-dicarbonyl cleavage reactions of corresponding tricarbonyl compounds as intermediates of the oxidation.

PROCESSES FOR CONVERSION OF BIOLOGICALLY DERIVED MEVALONIC ACID

The invention relates to a process comprising reacting mevalonic acid, or a solution comprising mevalonic acid, to yield a first product or first product mixture, optionally in the presence of a solid catalyst and/or at elevated temperature and/or pressure. The invention further relates to a process comprising: (a) providing a microbial organism that expresses a biosynthetic mevalonic acid pathway; (b) growing the microbial organism in fermentation medium comprising suitable carbon substrates, whereby biobased mevalonic acid is produced; and (c) reacting said biobased mevalonic acid to yield a first product or first product mixture.