4460-42-8

Usage

Uses

Used in Flavor and Fragrance Industry:
1-(5-ethyl-2,4-dihydroxy-phenyl)ethanone is used as a flavoring agent and fragrance ingredient for its sweet, floral scent, enhancing the sensory profiles of various consumer products.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 1-(5-ethyl-2,4-dihydroxy-phenyl)ethanone is used as a key intermediate in the synthesis of various pharmaceutical compounds, leveraging its reactive functional groups for the development of new drugs.
Used as a Reagent in Organic Synthesis:
1-(5-ethyl-2,4-dihydroxy-phenyl)ethanone serves as a reagent in organic synthesis, facilitating a range of chemical reactions due to its aromatic and hydroxyl groups, which are essential for the formation of new chemical entities.
Used in Antioxidant and Antifungal Applications:
Due to its antioxidant and antifungal properties, 1-(5-ethyl-2,4-dihydroxy-phenyl)ethanone is used in the development of pharmaceutical and cosmetic products, where it can help protect against oxidative stress and fungal infections, respectively.
Used in Cosmetics Industry:
In the cosmetics industry, 1-(5-ethyl-2,4-dihydroxy-phenyl)ethanone is used as an active ingredient for its antioxidant properties, potentially contributing to the formulation of skincare products that aim to protect and nourish the skin.

Upstream product

• 2896-60-8 4-ethyl-1,3-benzenediol 
• 127265-10-5 4-ethylresorcinol acetate 
• 75-36-5 acetyl chloride 
• 75-05-8 acetonitrile 
• 64-19-7 acetic acid 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 625-60-5 ethyl thioacetate 
• 373-61-5 boron trifluoride diacetate 
• 2161-86-6 2,4-diacetylphloroglucinol 
• 108-22-5 Isopropenyl acetate 
• 2466-76-4 N-Acetylimidazole 
• 4223-83-0 5-ethyl-6-methoxy-2,3-dimethyl-benzofuran 
• 108-46-3 recorcinol 

Downstream Products

• 26081-90-3 6-ethyl-7-hydroxy-2-phenyl-chroman-4-one 
• 33854-24-9 5'-ethyl-2',4'-dihydroxy-trans-chalcone 
• 101594-92-7 1-(4-(benzyloxy)-5-ethyl-2-hydroxyphenyl)ethan-1-one 
• 117690-97-8 5-(4-Acetyl-2-ethyl-5-hydroxyphenoxy)-pentanenitrile 
• 117690-59-2 7-(4-acetyl-2-ethyl-5-hydroxyphenoxy)heptanenitrile 
• 117690-81-0 7-(4-acetyl-2-ethyl-5-hydroxyphenoxy)-2,2-dimethylheptanenitrile 
• 140660-27-1 4-(4-Acetyl-2-ethyl-5-hydroxy-phenoxymethyl)-benzonitrile 
• 117690-78-5 3-[(4-Acetyl-2-ethyl-5-hydroxyphenoxy)-methyl]benzonitrile 
• 1026410-89-8 {3-[3-(4-Acetyl-2-ethyl-5-hydroxy-phenoxy)-propoxy]-phenyl}-acetic acid ethyl ester 
• 1027191-90-7 {4-[3-(4-Acetyl-2-ethyl-5-hydroxy-phenoxy)-propoxy]-phenyl}-acetic acid ethyl ester 
• 1025930-22-6 4-[5-(4-Acetyl-2-ethyl-5-hydroxy-phenoxy)-pentyloxy]-benzoic acid ethyl ester 
• 1027312-15-7 {2-[3-(4-Acetyl-2-ethyl-5-hydroxy-phenoxy)-propoxy]-phenyl}-acetic acid ethyl ester 
• 1027372-98-0 3-{4-[3-(4-Acetyl-2-ethyl-5-hydroxy-phenoxy)-propoxy]-phenyl}-propionic acid ethyl ester 
• 1026318-81-9 {4-[5-(4-Acetyl-2-ethyl-5-hydroxy-phenoxy)-pentyloxy]-phenyl}-acetic acid ethyl ester 

Relevant academic research and scientific papers

Thioesters as Acyl Donors in Biocatalytic Friedel-Crafts-type Acylation Catalyzed by Acyltransferase from Pseudomonas Protegens

Functionalization of aromatic compounds by acylation has considerable significance in synthetic organic chemistry. As an alternative to chemical Friedel-Crafts acylation, the C-acyltransferase from Pseudomonas protegens has been found to catalyze C?C bond formation with non-natural resorcinol substrates. Extending the scope of acyl donors, it is now shown that the enzyme is also able to catalyze C?S bond cleavage prior to C?C bond formation, thus aliphatic and aromatic thioesters can be used as acyl donors. It is worth to mention that this reaction can be performed in aqueous buffer. Identifying ethyl thioacetate as the most suitable acetyl donor, the products were obtained with up to >99 % conversion and up to 88 % isolated yield without using additional base additives; this represents a significant advancement to prior protocols.

Biocatalytic Friedel–Crafts Acylation and Fries Reaction

The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries rearrangement-like reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C?C bond formation methods.

Phenyl 1, 2 - isoxazole or phenyl 1, 2 - pyrazole compound and use thereof (by machine translation)

The invention discloses the following formula of phenyl 1, 2 - different oxazole or 1, 2 - pyrazole compounds with use. Through the biological activity tests show that, the compound inhibiting heat shock protein 90 activity. Therefore, the invention phenyl 1, 2 - different oxazole or 1, 2 - pyrazole compounds can be used as a heat shock protein 90 inhibitor for the treatment of cancer. (by machine translation)

Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists

Compound 1 (IC50 = 35.2 ± 7.2 μM), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 ± 0.1 μM. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity.

4,5-Diarylisoxazole Hsp90 chaperone inhibitors: Potential therapeutic agents for the treatment of cancer

Inhibitors of the Hsp90 molecular chaperone are showing considerable promise as potential chemotherapeutic agents for cancer. Here, we describe the structure-based design, synthesis, structure - activity relationships and pharmacokinetics of potent small-molecule inhibitors of Hsp90 based on the 4,5-diarylisoxazole scaffold. Analogues from this series have high affinity for Hsp90, as measured in a fluorescence polarization (FP) competitive binding assay, and are active in cancer cell lines where they inhibit proliferation and exhibit a characteristic profile of depletion of oncogenic proteins and concomitant elevation of Hsp72. Compound 40f (VER-52296/NVP-AUY922) is potent in the Hsp90 FP binding assay (IC50 = 21 nM) and inhibits proliferation of various human cancer cell lines in vitro, with GI50 averaging 9 nM. Compound 40f is retained in tumors in vivo when administered i.p., as evaluated by cassette dosing in tumor-bearing mice. In a human colon cancer xenograft model, 40f inhibits tumor growth by ～50%.

Discovery of hydroxamic acid analogs as dual inhibitors of phosphodiesterase-1 and -5

HTS and the following synthesis of a series of the compounds led us to the discovery of hydroxamic acid analogs as potent dual inhibitors of phosphodiesterase (PDE)-1 and 5. These compounds have highly related structure and deviation of the structure usua

Synthesis and study of antibacterial activity of some Schiff bases derived from sulfonamide, 4-amino antipyrene and raceacetophenone

Schiff bases derived from sulfonamide, 4-amino antipyrene and raceacetophenone were screened for antibacterial activity against various clinical isolates (obtained from Urine, Blood, Tracheal secretion and Pus). Extracts of these compounds were evaluated on 5 pathogenic strains [E. coli, Pseudomonas aeruginosa, Proteus vulgaris, Klebsiella pneumoniae and Staphylococcus aureus]. The antibacterial activity was evaluated using the Agar Ditch method. The Schiff bases produced were (1) 4-[2-aza-2- (2-chlorophenyl) vinyl] benzene sulfonamide [AD1] (2) 4-[2-aza-2- (2-hydroxyphenyl) vinyl] benzene sulfonamide [AD2] (3) [1-aza-4-phenylbuta-1, 3-dienyl] benzene sulfonamide [AD3] (4) 4-[1-aza-2- (2chlorophenyl) vinyl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one [AS1] (5) 4-[1-aza-2-(2-hydroxyphenyl) vinyl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one [AS2] (6) 4-[1-aza-4-phenylbuta-1, 3-dienyl] 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one [AS3] (7) 4-[2-aza-1-methyl-2- (2-nitro phenyl) vinyl]-6-ethylbenzene-1, 3-diol [ADS1] (8) 4-[2-aza-2(5-ehtyl-2, 4-dihydroxyphenyl) prop-1-enyl] benzene sulfonamide [ADS2]. The anti bacterial activity of these Schiff bases, were evaluated in one polar and one non polar (i.e., DMF and 1,4 dioxan) solvents. It is found that among AD and AS compounds AD compounds are better than AS and AD3 is the best while 1,4 dioxan solvent proved to be more effective than DMF. It appears that the sulfonamide moiety present with cinnamaldehyde side chain could be used as a lead molecule in drug designing (i.e. in inhibiting the above pathogenic bacteria).

Leukotriene B4 Receptor Antagonists: The LY255283 Series of Hydroxyacetophenones

A series of hydroxyacetophenones was prepared for evaluation as leukotriene B4 (LTB4) receptor antagonists, culminating in 1-oxy>phenyl>ethanone (compound 35, LY255283).Using an assay for inhibition of specific LTB4 binding to human PMN, we found that substitution of a nonpolar substituent in the 5-position was required for activity.Best activity was realized with hydrogen in the 3-position, hydroxyl in the 2-position, short chain alkyl ketone in the 1-position, and a six- or eight-carbon chain linking the oxygen in the 4-position with an unsaturated terminal function.Compound 35, having an IC50 of 87 nM in the binding assay, was chosen for further preclinical evaluation.

ANTI-INFLAMMATORY AGENTS

This invention provides benzene derivatives, pharmaceutical formulations of those derivatives, and a method of using the derivatives for the treatment of inflammation in mammals.