140-86-3

Basic information

• Product Name: 1,4-Dihydroxy-2-butanone
• Synonyms: 1,4-Dihydroxy-2-butanone;3-Deoxytetrulose
• CAS NO: 140-86-3
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.10452
• Mol File: 140-86-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 242.692°C at 760 mmHg
• Flash Point: 114.843°C
• Appearance: /
• Density: 1.201g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.459
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1,4-Dihydroxy-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Dihydroxy-2-butanone(140-86-3)
• EPA Substance Registry System: 1,4-Dihydroxy-2-butanone(140-86-3)

Safety Data

• Hazardous Substances Data: 140-86-3(Hazardous Substances Data)

Usage

General Description

1,4-Dihydroxy-2-butanone, also known as DHB, is a chemical compound with the molecular formula C4H8O3. It is a type of ketone and is commonly found in nature as a byproduct of various metabolic processes. DHB is also an important intermediate in the biosynthesis of the amino acid threonine. It has been used as a standard for measuring the activity of the enzyme transketolase, which is involved in the pentose phosphate pathway. Additionally, DHB has been studied for its potential antioxidant and antibacterial properties. Overall, 1,4-Dihydroxy-2-butanone plays several important roles in biological processes and has potential applications in various fields.

InChI:InChI=1/C4H8O3/c5-2-1-4(7)3-6/h5-6H,1-3H2

Upstream product

• 110-65-6 1,4-dihydroxybut-2-yne 
• 7664-93-9 sulfuric acid 
• 50-00-0 formaldehyd 
• 116-09-6 hydroxy-2-propanone 
• 101-27-9 barban 
• 52642-66-7 hydroxymethylvinyl ketone 
• 3068-00-6 D,L-1,2,4-butanetriol 

Downstream Products

• 43002-61-5 2-(2-phenyl-1⁽³⁾H-imidazol-4-yl)-ethanol 
• 872-82-2 2-(1H-imidazol-4-yl)ethanol 
• 584-03-2 1,2-dihydroxybutane 
• 1026412-65-6 2-[2-(3,3-diphenylpropyl)-1H-imidazol-4-yl]ethanol 
• 178920-25-7 2-[2-(3-Bromo-phenyl)-1H-imidazol-4-yl]-ethanol 
• 149071-53-4 2-{2-[6-(3-Piperidin-1-ylmethyl-phenoxy)-hexyl]-1H-imidazol-4-yl}-ethanol 
• 149071-68-1 2-{2-[3-(3-Piperidin-1-ylmethyl-phenoxy)-propyl]-1H-imidazol-4-yl}-ethanol 
• 149071-72-7 2-{2-[3-(3-Pyrrolidin-1-ylmethyl-phenoxy)-propyl]-1H-imidazol-4-yl}-ethanol 
• 149071-70-5 2-{2-[3-(3-Dimethylaminomethyl-phenoxy)-propyl]-1H-imidazol-4-yl}-ethanol 
• 102151-59-7 2-<4-(benzyloxy)phenyl>-4-(2-hydroxyethyl)imidazole 
• 38982-28-4 1-acetoxybut-3-en-2-one 
• 33245-14-6 1,4-diacetoxy-2-butanone 
• 3068-00-6 D,L-1,2,4-butanetriol 

Relevant articles and documents

Oxidation of Vicinal Diols to α-Hydroxy Ketones with H2O2 and a Simple Manganese Catalyst

α-Hydroxy ketones are valuable synthons in organic chemistry. Here we show that oxidation of vic-diols to α-hydroxy ketones with H2O2 can be achieved with an in situ prepared catalyst based on manganese salts and pyridine-2-carboxylic acid. Furthermore the same catalyst is effective in alkene epoxidation, and it is shown that alkene oxidation with the MnII catalyst and H2O2 followed by Lewis acid ring opening of the epoxide and subsequent oxidation of the alkene to α-hydroxy ketones can be achieved under mild (ambient) conditions.

Chemoselective oxidation of polyols with chiral palladium catalysts

Chiral palladium-based catalysts derived from pyridinyl oxazoline (pyOx) ligands catalyze the oxidation of alcohols, including 1,2-diols, triols, and tetraols, with high regio- and chemoselectivity. Screening of various chiral oxazoline-derived ligands for the oxidation of a model diol, 1,2-propanediol (1,2-PD), revealed that the nature of the ligand had a significant influence on the activity and chemoselectivity for oxidation of vicinal diols. The PyOx ligands containing an α-methyl substituent were the most active for the oxidation of 1,2-PD using benzoquinone as the terminal oxidant. Oxidation of vicinal diols and polyols occurs selectively at the secondary alcohol to afford α-hydroxy ketones in isolated yields of 62-87%. Chemoselective oxidation of meso-erythritol with the chiral [(S)-(α-Me(tert-Bu)PyOx)Pd(OAc)] 2[OTf]2 afforded (S)-erthyrulose in 62% yield and 24% ee.

Microbial Transformation of sec-Hydroxyl Group of Polyols into Carbonyl Derivatives by Specific Oxidation Using Methanol Yeast

sec-Hydroxyl group of polyol was oxidized to the corresponding carbonyl derivative using methanol yeast, Candida boidinii KK912.Thus 1,2,4-butanetriol was oxidized for 2 days to give 1,4-dihydroxy-2-butanone in 78.1percent yield.The microbial oxidation for analogous polyols was also discussed.