3142-66-3

Usage

Uses

Used in Flavor and Fragrance Industry:
Hydroxypentanone, 3-hydroxy-2-pentanone is used as a key compound for creating various flavors and fragrances due to its distinct aromatic properties. It contributes to the characteristic taste and smell of products in this industry.
Used in Pharmaceutical Industry:
Hydroxypentanone, 3-hydroxy-2-pentanone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Food Industry:
Hydroxypentanone, 3-hydroxy-2-pentanone is used as an additive in the food industry to enhance the taste and aroma of various products. Its natural occurrence in certain foods, such as yogurt, asparagus, and cheese, makes it a suitable candidate for improving the sensory qualities of these items.
Used in Cosmetic Industry:
Hydroxypentanone, 3-hydroxy-2-pentanone is used as a component in the formulation of cosmetics, particularly in perfumes and fragrances. Its ability to create unique scents makes it a valuable asset in the development of personal care products.
Used in Chemical Synthesis:
Hydroxypentanone, 3-hydroxy-2-pentanone is used as a versatile building block in the synthesis of various organic compounds. Its reactivity and functional groups make it a useful starting material for creating a wide range of chemicals with diverse applications.

InChI:InChI=1/C5H10O2/c1-3-5(7)4(2)6/h5,7H,3H2,1-2H3

Upstream product

• 600-14-6 2,3-Pentanedione 
• 591-95-7 penta-1,2-diene 
• 5704-20-1 2-hydroxy-3-pentanone 
• 875225-67-5 4-methoxy-4-methyl-octane-3,5-diol 
• 600-18-0 2-Oxobutyric acid 
• 75-07-0 acetaldehyde 
• 123-38-6 propionaldehyde 
• 127-17-3 2-oxo-propionic acid 
• 546-67-8 lead(IV) tetraacetate 
• 71-43-2 benzene 
• 103205-82-9 2,3-dihydroxy-2-methyl-valeraldehyde 
• 4187-86-4 pent-1-yn-3-ol 
• 5551-19-9 3-ethyl-2-formyloxy-2-methyl-oxirane 
• 18218-93-4 2-methoxyacrolein 

Downstream Products

• 600-14-6 2,3-Pentanedione 
• 42027-23-6 2,3-pentanediol 
• 3896-13-7 pentane-2,3-dione-bis-phenylhydrazone 
• 64-19-7 acetic acid 
• 123-38-6 propionaldehyde 
• 1455438-47-7 3-(4-methoxyphenylamino)pentan-2-one 

Relevant academic research and scientific papers

Synthesis of α-hydroxy ketones and vicinal (R, R)-diols by Bacillus clausii DSM 8716T butanediol dehydrogenase

α-hydroxy ketones (HK) and 1,2-diols are important building blocks for fine chemical synthesis. Here, we describe the R-selective 2,3-butanediol dehydrogenase from B. clausii DSM 8716T (BcBDH) that belongs to the metal-dependent medium chain dehydrogenases/reductases family (MDR) and catalyzes the selective asymmetric reduction of prochiral 1,2-diketones to the corresponding HK and, in some cases, the reduction of the same to the corresponding 1,2-diols. Aliphatic diketones, like 2,3-pentanedione, 2,3-hexanedione, 5-methyl-2,3-hexanedione, 3,4-hexanedione and 2,3-heptanedione are well transformed. In addition, surprisingly alkyl phenyl dicarbonyls, like 2-hydroxy-1-phenylpropan-1-one and phenylglyoxal are accepted, whereas their derivatives with two phenyl groups are not substrates. Supplementation of Mn2+ (1 mM) increases BcBDH's activity in biotransformations. Furthermore, the biocatalytic reduction of 5-methyl-2,3-hexanedione to mainly 5-methyl-3-hydroxy-2-hexanone with only small amounts of 5-methyl-2-hydroxy-3-hexanone within an enzyme membrane reactor is demonstrated.

Selective Hydrogenation of Diketones on Supported Transition Metal Catalysts

Abstract: The hydrogenation of α-diketones yields α-hydroxyketones or vic-diols, both compounds of great interest in fine chemistry. The reaction tests were the liquid phase hydrogenation of 2,3-butanedione and 2,3-pentanedione at mild conditions. The objectives of this work were evaluating the effect over the activity and selectivity of: (a) different transition metallic phase based catalysts supported on activated carbon, (b) the symmetry of the reactants and (c) solvents. The physicochemical characterization of the catalysts was carried out by ICP, XRD, TEM, N2 adsorption and XPS. The keto-enol equilibrium of diketones was studied by 1H-NMR. All the catalysts were active in both reactions. In terms of activity, Pt and Rh were the best active phases. For both reactants the highest selectivity towards hydroxyketones were achieved with Pd, while Ru was the most selective towards the diol. Both the activity and selectivity followed similar patterns in the hydrogenation of both diketones. The greater activity of Pt was attributed to the high dispersion of the active metal phase in this catalyst and the high efficiency of Pt for C = O bond reduction. The high selectivity of the Pd catalysts towards the intermediate product was attributed to many effects: (i) a lower interaction of the hydroxyketone with the active site as compared to the diketone, (ii) the easy reducibility of the C = C double bond on Pd, provided by the keto-enol tautomerism of diketones.

Engineering transketolase to accept both unnatural donor and acceptor substrates and produce α-hydroxyketones

A narrow substrate range is a major limitation in exploiting enzymes more widely as catalysts in synthetic organic chemistry. For enzymes using two substrates, the simultaneous optimisation of both substrate specificities is also required for the rapid expansion of accepted substrates. Transketolase (TK) catalyses the reversible transfer of a C2-ketol unit from a donor substrate to an aldehyde acceptor and suffers the limitation of narrow substrate scope for industrial applications. Herein, TK from Escherichia?coli was engineered to accept both pyruvate, as a novel donor substrate, and unnatural acceptor aldehydes, including propanal, pentanal, hexanal and 3-formylbenzoic acid (FBA). Twenty single-mutant variants were first designed and characterised experimentally. Beneficial mutations were then recombined to construct a small library. Screening of this library identified the best variant with a 9.2-fold improvement in the yield towards pyruvate and propionaldehyde, relative to wild-type (WT). Pentanal and hexanal were used as acceptors to determine stereoselectivities of the reactions, which were found to be higher than 98% enantiomeric excess (ee) for the S configuration. Three variants were identified to be active for the reaction between pyruvate and 3-FBA. The best variant was able to convert 47% of substrate into product within 24?h, whereas no conversion was observed for WT. Docking experiments suggested a cooperation between the mutations responsible for donor and acceptor recognition, which would promote the activity towards both the acceptor and donor. The variants obtained have the potential to be used for developing catalytic pathways to a diverse range of high-value products.

Preparation Method for 2,3-pentanedione

A preparation method for 2,3-pentanedione, including the steps of adding one or both of 3-hydroxy-2-pentanone and 2-hydroxy-3-pentanone into water and conducting mixing, and introducing ozone at the temperature of 3-20° C. for a reaction to obtain 2,3-pentanedione. The synthesis process of the present invention uses ozone for oxidizing a mixture containing 3-hydroxy-2-pentanone and 2-hydroxy-3-pentanone, acetic acid is used as a cocatalyst, reaction conditions are mild, the operation process is simple, the product yield is high, and the cost is low.

Preparation method of 2,3-pentanedione

The invention discloses a preparation method of 2,3-pentanedione. The preparation method comprises the following steps: one or two of 3-hydroxy-2-pentanone and 2-hydroxy-3-pentanone is/are added to water and uniformly mixed with water, ozone is introduced at the temperature of 3-20 DEG C for a reaction, and 2,3-pentanedione is obtained. According to the synthesis process, ozone is adopted to oxidize the mixture containing 3-hydroxy-2-pentanone and 2-hydroxy-3-pentanone, acetic acid is adopted as a cocatalyst, reaction conditions are mild, and operation process is simple; product yield is high;cost is low; the method has the advantages of being safe and environmentally friendly, and no wastewater is produced.

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.

PROCESS INCLUDING HYDROGENOLYSIS OF BIOMASS FOLLOWED BY DEHYDROGENATION AND ALDOL CONDENSATION FOR PRODUCING ALKANES

A method comprises providing a bio-based feedstock; contacting the bio-based feedstock with a solvent in a hydrolysis reaction to form an intermediate stream comprising carbohydrates; contacting the intermediate stream with an aqueous phase reforming catalyst to form a plurality of oxygenated intermediates, wherein a first portion of the oxygenated intermediates are recycled to form the solvent; and contacting at least a second portion of the oxygenated intermediates with a condensation catalyst comprising a base functionality to form a fuel blend.

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.

Adducts of thianthrene- and phenoxathiin cation radical tetrafluoroborates to 1-alkynes. Structures and formation of 1-(5-thianthreniumyl)- and 1-(10-phenoxathiiniumyl)alkynes on alumina leading to α-ketoylides and α-ketols

Thianthrene cation radical tetrafluoroborate (Th.+BF 4-) added to the terminal alkynes 1-pentyne, 1-hexyne, 1-heptyne, 1-octyne, 1-nonyne, and 1-decyne to form trans-1,2-bis(5- thianthreniumyl)-alkene tetrafluoroborates (1-6). Similarly, addition of phenoxathiin cation radical tetrafluoroborate (PO.+BF 4-) to the same alkynes gave 1,2-bis(10-phenoxathiiniumyl) alkene tetrafluoroborates (7-12). The trans configuration of two of the adducts (1 and 4) was shown with X-ray crystallography. When solutions of 1-6 in chloroform were stirred with activated alumina, cis elimination of a proton and thianthrene (Th) occurred with the formation of 1-(5-thianthreniumyl)alkyne tetrafluoroborates (1a-6a). Similar treatment of 8-12 caused elimination of a proton and phenoxathiin (PO) with formation of 1-(10-phenoxathiiniumyl)alkene tetrafluoroborates (8a-12a). Stirring of 1a-6a with alumina for short periods of time caused their conversion into 5-[(α-keto)alkyl]thianthrenium ylides (1b-6b) and α-ketols, RC(O)CH2OH (1c-6c).

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.