5355-63-5

Usage

Uses

Used in Flavor and Fragrance Industry:
3-HYDROXY-4-PHENYLBUTAN-2-ONE is used as a flavoring agent for its pleasant and creamy sweet fragrance, enhancing the taste and aroma of various food and beverage products.
Used in Perfumery:
3-HYDROXY-4-PHENYLBUTAN-2-ONE is used as a fixative in the perfumery industry, where its warm and mild fragrance helps to stabilize and prolong the scent of perfumes and colognes.
Used in Pharmaceutical Industry:
3-HYDROXY-4-PHENYLBUTAN-2-ONE can be used as an intermediate in the synthesis of various pharmaceutical compounds, potentially contributing to the development of new drugs with diverse therapeutic applications.
Used in Cosmetics:
3-HYDROXY-4-PHENYLBUTAN-2-ONE may be utilized in the cosmetics industry for its fragrance, where it can be incorporated into various products such as lotions, creams, and shampoos to provide a pleasant and appealing scent.
Used in Research and Development:
3-HYDROXY-4-PHENYLBUTAN-2-ONE can be employed as a research compound for studying its chemical properties, potential applications, and interactions with other molecules, which may lead to the discovery of new uses and benefits in various industries.

Preparation

Reported prepared by a Japanese Patent (details not available)

InChI:InChI=1/C10H12O2/c1-8(11)10(12)7-9-5-3-2-4-6-9/h2-6,10,12H,7H2,1H3

Upstream product

• 122-78-1 phenylacetaldehyde 
• 917-64-6 methyl magnesium iodide 
• 93554-96-2 α-<(trimethylsilyl)oxy>benzenepropanenitrile 
• 6249-79-2 1-(3-phenyloxiran-2-yl)ethanone 
• 119554-23-3 4-Phenyl-3-trimethylsilanyloxy-butan-2-one 
• 60-29-7 diethyl ether 
• 6249-79-2 trans-2-acetyl-3-phenyloxirane 
• 64-17-5 ethanol 
• 65248-91-1 3-oxo-1-phenylbutan-2-yl acetate 
• 620-76-8 phenylpyruvate^- 
• 75-07-0 acetaldehyde 
• 1896-62-4 (E)-benzalacetone 
• 135663-97-7 1-phenylbut-3-yn-2-ol 
• 2550-26-7 4-Phenyl-2-butanone 

Downstream Products

• 65248-91-1 3-oxo-1-phenylbutan-2-yl acetate 
• 5381-89-5 1-phenylbutane-2,3-diol 

Relevant academic research and scientific papers

Cu-catalyzed synthesis of tetrasubstituted 2,3-allenols through decarboxylative silylation of alkyne-substituted cyclic carbonates

An efficient and mild Cu-catalyzed protocol has been developed for the decarboxylative silylation of alkyne-functionalized cyclic carbonate substrates affording 2,3-allenols featuring four different substituents. This practical methodology gives access to a wide scope of tetrasubstituted functionalized allenes in excellent yields.

Α - hydroxy ketone compound low priced high-efficient synthetic method

The invention discloses a cheap and efficient synthesis method of an alpha-hydroxyketone compound. The synthesis method is characterized in that a carbonyl compound undergoes an oxidation hydroxylation reaction at 10-120DEG C under normal pressure with iodine simple substance, N-bromosuccimide, copper bromide, bromine simple substance, hydrogen bromide, N-iodosuccimide or hydrogen iodide as a catalyst, sulfoxide as an oxidant, water or sulfoxide as a hydroxy source and sulfoxide, ethyl acetate, N,N-dimethyl formamide, acetonitrile, toluene, 1,4-dioxane, 1,2-dichloroethane, tetrahydrofuran or H2O as a solvent, and converts into the alpha-hydroxyketone compound in a high selectivity manner. Compared with traditional synthesis methods, the method disclosed in the invention has the advantages of simple operation, high yield, simple conditions, easy purification, small waste discharge amount, simple reaction apparatus, and easy industrial production. The method has wide applicability and can be used for synthesizing various alpha-hydroxyketone compounds.

I2- or NBS-catalyzed highly efficient α-hydroxylation of ketones with dimethyl sulfoxide

An efficient method for the direct preparation of high synthetic valuable α-hydroxycarbonyls is described. The simple and readily available I2 or NBS was used as catalyst. DMSO acts as the oxidant, oxygen source, and solvent. A diverse range of tertiary Csp3-H bonds as well as more challenging secondary Csp3-H bonds could be hydroxylated in this transformation. The reaction is mild, less toxic and easy to perform.

[(NHC)AuCl]-catalyzed Meyer-Schuster rearrangement: scope and limitations

An efficient catalytic system allowing for the synthesis of a variety of α,β-unsaturated ketones has been developed. [(NHC)AuCl] (NHC{double bond, long}N-heterocyclic carbene) in the presence of a silver(I) salt was found to catalyze the Meyer-Schuster rearrangement, leading to α,β-unsaturated ketones from easily accessible propargylic alcohols in high yields. Catalysis was performed in a 2:1 mixture of methanol and water at 60 °C and afforded good yields even for tertiary alcohols and sterically demanding substrates. Thorough evaluation of the present catalytic system uncovered that it was unsuitable for terminal alkynes and primary alcohols. In these cases low yields of the target molecules were obtained due to the formation of unexpected by-products.

Branched-chain keto acid decarboxylase from Lactococcus lactis (KdcA), a valuable thiamine diphosphate-dependent enzyme for asymmetric C - C bond formation

The thiamine diphosphate-dependent, branched-chain 2-keto acid decarboxylase from Lactococcus lactis sup. cremoris Bl157 (KdcA) is a new valuable enzyme for the synthesis of chiral 2-hydroxy ketones. The gene was cloned and the enzyme was expressed as an

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.

HISTONE DEACETYLASE INHIBITORS BASED ON ALPHACHALCOGENMETHYLCARBONYL COMPOUNDS

Histone deacetylase is a metallo-enzyme with zinc at the active site. Compounds having a zinc-binding moiety, for example, an alpha-chalcogenmethylcarbonyl group, such as an alpha-ketothio group, can inhibit histone deacetylase. Histone deacetylase inhibition can repress gene expression, including expression of genes related to tumor suppression. Accordingly, inhibition of histone deacetylase can provide an alternate route for treating cancer, hematological disorders, e.g., hemoglobinopathies, autosomal dominant disorders, e.g. spinal muscular atrophy and Huntington’s disease, genetic related metabolic disorders, e.g., cystic fibrosis and adrenoleukodystrophy, or for stimulating hematopoietic cells ex vivo.

Recyclable Polyurea-Microencapsulated Pd(0) Nanoparticles: An Efficient Catalyst for Hydrogenolysis of Epoxides

(Matrix presented) Pd nanoparticles (～2 nm in size) microencapsulated in polyurea is an efficient and recyclable catalyst for reductive ring-opening hydrogenolysis of epoxides, using either HCOOH/Et3N or H2 as a hydrogen donor.

Studies on irreversible inhibition of serine proteases by α- sulfonyloxyketone derivatives

α-Sulfonyloxyketone derivatives were found to be active-site directed irreversible inhibitors of serine proteases.

Hydrogenolysis of α,β-Epoxyketone and Ester to Aldol in Pd(0)/HCOOH/Et3N and H2/Pd/C Reduction Media

Hydrogenation of α,β-epoxycarbonyl compounds by using several catalysts and hydride sources was studied to obtain the corresponding β-hydroxy substrates.