54123-75-0

Usage

Uses

Used in Chemical Industry:
2-Hexanone, 3-hydroxy(6CI,9CI) is used as a solvent for various applications due to its ability to dissolve a wide range of substances.
Used in Perfume and Flavoring Industry:
2-Hexanone, 3-hydroxy(6CI,9CI) is used in the production of perfumes and flavorings, contributing to the creation of various scents and tastes.
Used in Pharmaceutical Industry:
2-Hexanone, 3-hydroxy(6CI,9CI) is used as a starting material in the synthesis of various pharmaceuticals, playing a crucial role in the development of new medications.
Used in Research and Development:
2-Hexanone, 3-hydroxy(6CI,9CI) is studied for its potential use in the treatment of neurological disorders and as an analgesic, indicating its potential in advancing medical treatments.
It is important to handle 2-Hexanone, 3-hydroxy(6CI,9CI) with caution as it can be harmful if inhaled, ingested, or in contact with skin.

InChI:InChI=1/C6H12O2/c1-3-4-6(8)5(2)7/h6,8H,3-4H2,1-2H3

Upstream product

• 64-18-6 formic acid 
• 15352-99-5 (+/-)-hex-1-yn-3-yl acetate 
• 107-08-4 1-iodo-propane 
• 127-06-0 acetone oxime 
• 591-78-6 n-hexan-2-one 
• 3848-24-6 2,3-hexanedione 
• 113-24-6 sodium pyruvate 
• 123-72-8 butyraldehyde 
• 92675-74-6 2-oxohexan-3-yl acetate 
• 116016-09-2 3-iodo-2-hexanone 
• 57-60-3 piruvate 
• 1579999-30-6 2-ethoxyhex-1-en-3-ol 
• 67-56-1 methanol 
• 415900-43-5 tert-butyl 2-acetoxy-2-acetylpentanoate 

Downstream Products

• 3848-24-6 2,3-hexanedione 
• 100255-75-2 2-[(2,4-Dinitro-phenyl)-hydrazono]-hexan-3-ol 

Relevant academic research and scientific papers

Synthesis of aggregation pheromone components of cerambycid species through α-hydroxylation of alkylketones

The synthesis of 3-hydroxy-2-hexanone and 2,3-hexanediol, two components of the aggregation pheromone of several cerambycid species, is disclosed in here. Starting from 2-hexanone, through an α-hydroxylation using (diacetoxyiodo)benzene, 3-hydroxy-2-hexanone is obtained in good yield. Further reduction of this compound, gives 2,3-hexanediol in excellent yield. A study of the α-hydroxylation reaction of several alkylketones using an hypervalent iodine reagent is also disclosed in here. The synthesis of optically active compounds (R)- and (S)-3-hydroxy-2-hexanone was achieved starting from 2-hexanone with nitrosobenzene and L- and D-proline respectively, in several reaction media.

Synthesis and Characterization of Urofuranoic Acids: In Vivo Metabolism of 2-(2-Carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic Acid (CMPF) and Effects on in Vitro Insulin Secretion

CMPF (2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid) is a metabolite that circulates at high concentrations in type 2 and gestational diabetes patients. Further, human clinical studies suggest it might have a causal role in these diseases. CMPF inhibits insulin secretion in mouse and human islets in vitro and in vivo in rodents. However, the metabolic fate of CMPF and the relationship of structure to effects on insulin secretion have not been significantly studied. The syntheses of CMPF and analogues are described. These include isotopically labeled molecules. Study of these materials in vivo has led to the first observation of a metabolite of CMPF. In addition, a wide range of CMPF analogues have been prepared and characterized in insulin secretion assays using both mouse and human islets. Several molecules that influence insulin secretion in vitro were identified. The molecules described should serve as interesting probes to further study the biology of CMPF.

Revealing substrate promiscuity of 1-deoxy-D-xylulose 5-phosphate synthase

A study of DXP synthase has revealed flexibility In the acceptor substrate binding pocket for nonpolar substrates and has uncovered new details of the catalytic mechanism to show that pyruvate can act as both donor and acceptor substrate.

Photo-irradiation of α-halo carbonyl compounds: A novel synthesis of α-hydroxy- and α,α′-dihydroxyketones

The reaction of α-halo ketones (α-iodocycloalkanones, α-bromocycloalkanones, α-iodo-β-alkoxy esters, and α-iodoacyclicketones) with irradiation under a high-pressure mercury lamp gave the corresponding α-hydroxyketones in good yields. For α-bromoketones, it was found that α-hydroxylation does not occur. However, α-bromoketones were converted into α-hydroxyketones in the presence of KI. In the case of α,α′-diiodo ketones, α,α′-dihydroxyketones, which up to now have scarcely been reported, were obtained. This reaction affords a new, clean and convenient synthetic method for α-hydroxy- and α,α′- dihydroxyketones.

A new route to protected acyloins and their enzymatic resolution with lipases

A series of 16 different 3-acyloxy methyl ketones, the acyloin acetates and butyrates (±)-5, was synthesised by a straight-forward new method through alkylation of tert-butyl 2-acyloxyacetoacetates 3, followed by chemoselective dealkoxy-carbonylation of the tert-butyloxycarbonyl group in the presence of other ester groups. Subsequent hydrolysis of (±)-5 can be achieved with base to give racemic acyloins 6, or with lipase catalysis to afford the corresponding non-racemic acyloins (S)-6. The remaining (R)-acyloin esters 5 can be racemised and resubjected to the procedure, or hydrolysed chemically. The kinetic resolution with two of the six tested enzymes, CAL-B and BCL (PS) lipase, proceeded selectively [enantiomeric ratio (E) values between 50 and > 200] and most of the acyloins (S)-6 were obtained in very high enantiomeric excesses (up to > 99% ee). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Chemoenzymatic synthesis of aroma active 5,6-dihydro- and tetrahydropyrazines from aliphatic acyloins produced by baker's yeast

Twenty-five acyloins were generated by biotransformation of aliphatic aldehydes and 2-ketocarboxylic acids using whole cells of baker's yeast as catalyst. Six of these acyloins were synthesized and tentatively characterized for the first time. Subsequent chemical reaction with 1,2-propanediamine under mild conditions resulted in the formation of thirteen 5,6-dihydropyrazines and six tetrahydropyrazines. Their odor qualities were evaluated, and their odor thresholds were estimated. Among these pyrazine derivatives, 2-ethyl-3,5-dimethyl-5,6-dihydropyrazine (roasted, nutty, 0.002 ng/L air), 2,3-diethyl-5-methyl-5,6-dihydropyrazine (roasted, 0.004 ng/L air), and 2-ethyl-3,5-dimethyltetrahy-dropyrazine (bread crustlike, 1.9 ng/L air) were the most intensive-smelling aroma active compounds.

Mercuric triflate-TMU catalyzed hydration of terminal alkyne to give methyl ketone under mild conditions

Herein developed mercuric triflate-TMU catalyzed hydration of terminal alkyne is a mild procedure to give methyl ketone in excellent yield with high chemoselectivity. By using 0.05 eq of Hg(OTf)2·(TMU)2 and 3 eq of water, hydration takes place at a reasonable rate in acetonitrile.

Oxidation of ketone by palladium(II), α-hydroxyketone synthesis catalyzed by a bimetallic palladium(II) complex

A bimetallic palladium(II) complex containing a triketone ligand and a bridging dinitrogen ligand oxidizes ketones in aqueous THF to α-hydroxyketone by a direct air oxidation. While the normal synthesis of α-hydroxyketones involves a series of reactions, this synthesis performs the transformation in one step in a catalytic air oxidation. This synthesis does not involve an olefin and is almost unprecedented in transition metal catalysis. Its main virtue is its simplicity and actually it is an enolization reaction. Methanesulfonic acid is used to accelerate the enolization of ketones. The reaction is carried out in the presence of CuCl2 and/or dioxygen only. In particular, it is found that the hydroxyketone formation does not require the presence of CuCl2. Matrix assisted laser desorption ionization (MALDI) and time-of-flight mass spectrometry (TOFMS) are used to record the mass spectra of α-hydroxyketones products. α-Cyano-4-hydroxycinnamic acid (CHCA) matrix promoted the molecular ion detection when 180 pmol of α-hydroxyketones is introduced into the TOFMS.

Mixtures and compositions suitable for controlling Hylotrupes bajulus and Pyrrhidium sanguineum

A mixture containing one stereoisomer of 3-hydroxyhexan-2-one and two stereoisomers of hexane-2,3-diol, especially (3R)-3-hydroxy-hexan-2-one, (2R,3R)-hexane-2,3-diol and/or (2R,3R)-hexane-2,3-diol and compositions containing them and the use of the mixture and of the compositions for controllingHylotrupes bajulusandPyrrhidium sanguineumby means of the monitoring, capture or mating disruption method are described.

Reduction of 1,2-diketones with titanium tetraiodide: A simple approach to α-hydroxy ketones

1,2-Diketones are readily reduced with titanium tetraiodide to give α-hydroxy ketones in good to excellent yields. Regioselectivity on the reduction of unsymmetrical substrates is also discussed. (C) 2000 Elsevier Science Ltd.