2-Hydroxybutyric acid

Base Information

• Chemical Name: 2-Hydroxybutyric acid
• CAS No.: 600-15-7
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.106
• Hs Code.: 2918199090
• European Community (EC) Number: 209-985-3
• NSC Number: 6495
• UNII: O0ADR0I4H5
• DSSTox Substance ID: DTXSID8041903
• Nikkaji Number: J130.629D,J2.433.029J
• Wikipedia: 2-Hydroxybutyric_acid
• Wikidata: Q3288610
• Metabolomics Workbench ID: 1281
• ChEMBL ID: CHEMBL567588
• Mol file: 600-15-7.mol

Synonyms:2-hydroxybutanoic acid;2-hydroxybutyric acid;2-hydroxybutyric acid, (+-)-isomer;2-hydroxybutyric acid, (R)-isomer;2-hydroxybutyric acid, monosodium salt;2-hydroxybutyric acid, monosodium salt, (+-)-isomer;alpha-hydroxybutyrate

Chemical Property of 2-Hydroxybutyric acid

Chemical Property:

• Melting Point: 44 °C
• Refractive Index: 1.4298 (589.3 nm 20℃)
• Boiling Point: 238.3 °C at 760 mmHg
• PKA: pK1:3.65 (30°C)
• Flash Point: 112.2 °C
• PSA: 57.53000
• Density: 1.195 g/cm³
• LogP: -0.15810
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 104.047344113
• Heavy Atom Count: 7
• Complexity: 69.3

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-HydroxybutanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-41-37/38
• Safety Statements: 26-36/37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CCC(C(=O)O)O
• 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.

Technology Process of 2-Hydroxybutyric acid

There total 70 articles about 2-Hydroxybutyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-Oxobutyric acid (600-18-0) → 2-aminobutanoic acid (2835-81-6) + 2-Hydroxybutanoic acid (600-15-7,565-70-8)

Guidance literature:

With water; ammonium formate; [Rh(pentamethylcyclopentadiene)(2,2'-bipyridine)H₂O]SO₄; at 80 ℃; for 1h; pH=4.5; Product distribution / selectivity;

Reference yield:

butyric acid (107-92-6) → methanol (67-56-1) + formic acid (64-18-6) + glycolic Acid (79-14-1) + LACTIC ACID (849585-22-4,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + 4-hydroxybutanoic acid (591-81-1) + acetaldehyde (75-07-0,9002-91-9) + acetic acid (64-19-7,77671-22-8) + acetone (67-64-1) + 3-Hydroxybutyric acid (300-85-6,625-71-8,26063-00-3,29435-48-1) + 2-Hydroxybutanoic acid (600-15-7,565-70-8)

Guidance literature:

With potassium tetrachloroplatinate; iron(II) chloride tetrahydrate; sulfuric acid; oxygen; In water; at 150 ℃; for 6h; under 15001.5 Torr; Catalytic behavior;

DOI:10.1002/chem.201901803

Reference yield:

butyric acid (107-92-6) → methanol (67-56-1) + formic acid (64-18-6) + glycolic Acid (79-14-1) + LACTIC ACID (849585-22-4,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + 4-hydroxybutanoic acid (591-81-1) + succinic acid (110-15-6) + acetaldehyde (75-07-0,9002-91-9) + acetic acid (64-19-7,77671-22-8) + acetone (67-64-1) + 3-Hydroxybutyric acid (300-85-6,625-71-8,26063-00-3,29435-48-1) + 2-Hydroxybutanoic acid (600-15-7,565-70-8)

Guidance literature:

With potassium tetrachloroplatinate; iron(II) chloride tetrahydrate; sulfuric acid; oxygen; In water; at 150 ℃; for 6h; under 15001.5 Torr; Reagent/catalyst; Catalytic behavior;

DOI:10.1002/chem.201901803

upstream raw materials:

1,5-pentanedioic acid

2-chlorobutanoic acid

2-Bromobutyric acid

(+/-)-2-hydroxybutanal

Downstream raw materials:

2-hydroxy-butyric acid p-toluidide

2,2'-dinaphthylamine

(2S)-2-hydroxybutanoic acid

formic acid

Refernces

• 1、 Janssen, Michiel,De Vos, Dirk E.. "PtII-Catalyzed Hydroxylation of Terminal Aliphatic C(sp3)?H Bonds with Molecular Oxygen". supporting information. p. 10724 - 10734. Retrieved 2019/07/15.
• 2、 -. "PROCESSES FOR PREPARATION OF IDELALISIB AND INTERMEDIATES THEREOF". Page/Page column 34; 35. . Retrieved 2016/07/27.