35458-21-0

Usage

Uses

Used in Pharmaceutical Industry:
1-Propanone, 2-methyl-1-(2,4,6-trihydroxyphenyl)is used as an intermediate in the synthesis of Colupulone (C214755) for its antiradical and antioxidant activity. This makes it a potential candidate for the development of pharmaceutical products that target oxidative stress-related conditions and promote overall health.
Used in Cosmetic Industry:
Due to its antioxidant properties, 1-Propanone, 2-methyl-1-(2,4,6-trihydroxyphenyl)can be used in cosmetic formulations to protect the skin from free radicals and environmental damage, promoting a healthier and more youthful appearance.
Used in Food Industry:
As an antioxidant, 1-Propanone, 2-methyl-1-(2,4,6-trihydroxyphenyl)can be utilized in the food industry to extend the shelf life of products and maintain their quality by preventing oxidation and spoilage.
Used in Research and Development:
1-Propanone, 2-methyl-1-(2,4,6-trihydroxyphenyl)can be employed in research and development for the discovery of new antioxidants and antiradical agents, as well as for studying the mechanisms of oxidative stress and its impact on various diseases and conditions.

Upstream product

• 78-82-0 Isobutyronitrile 
• 108-73-6 3,5-dihydroxyphenol 
• 79-30-1 isobutyryl chloride 
• 79-31-2 isobutyric Acid 
• 513-36-0 isobutyryl chloride 
• 17004-75-0 1-[(2-methylpropanoyl)-5-hydroxyphloroglucinyl]-β-D-glucopyranoside 
• 74-88-4 methyl iodide 

Downstream Products

• 139409-38-4 4,4-Dibutyl-3,5-dihydroxy-2,6-diisobutyryl-cyclohexa-2,5-dienone 
• 35932-36-6 2-methyl-1-(2,4,6-trihydroxy-3-(3-methylbut-2-en-1-yl)phenyl)propan-1-one 
• 139409-37-3 4,4-Diethyl-3,5-dihydroxy-2,6-diisobutyryl-cyclohexa-2,5-dienone 
• 3467-13-8 5-hydroxy-4-(isobutyryl)-2,2,6,6-tetramethylcyclohex-4-ene-1,3-dione 
• 5880-42-2 {3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-propyl)-ketone 
• 54247-21-1 5-hydroxy-2,2,6,6-tetramethyl-4-(2-methyl-1-(2,4,6-trihydroxy-3-(1-(2-hydroxy-3,3,5,5-tetramethyl-4,6-dioxocyclohex-1-enyl)-2-methylpropyl)-5-isobutyrylphenyl)propyl)cyclohex-4-ene-1,3-dione 
• 1083197-75-4 5-hydroxy-2,2,6,6-tetramethyl-4-(3-methyl-1-(2,4,6-trihydroxy-3-isobutyrylphenyl)butyl)cyclohex-4-ene-1,3-dione 
• 198878-74-9 2,2-bis(3-methyl-2-butenyl)-3,5-dihydroxy-6-(2-methyl-1-oxopropyl)cyclohexa-3,5-dienone 
• 21621-94-3 Colupulone 
• 71539-57-6 3-<3',3'-dimethylallyl-(1')>-1-isobutyryl-phloroglucinol-6-O-methyl ether 
• 16981-20-7 5,7-dihydroxy-6-isobutyryl-8-(3-methylbut-2-enyl)-4-phenyl-2H-chromen-2-one 
• 16981-21-8 5,7-dihydroxy-6-(3-methylbut-2-enyl)-8-(2-methylpropanoyl)-4-phenylbenzopyran-2(2H)-one 
• 22628-86-0 2-Butyryl-4-isopentyl-phloroglucin 
• 71539-56-5 3'-(3-methyl-2-butenyl)-2',4',6'-triacetoxyisobutyrophenone 

Relevant academic research and scientific papers

Antibacterial Prenylated Acylphloroglucinols from Psorothamnus fremontii

Psorothatins A-C (1-3), three antibacterial prenylated acylphloroglucinol derivatives, were isolated from the native American plant Psorothamnus fremontii. They feature an unusual α,β-epoxyketone functionality and a β-hydroxy-α,β-unsaturated ketone struct

Biomimetic total syntheses of baefrutones A-D, baeckenon B, and frutescones A, D-F

Biomimetic total syntheses of baefrutones A-D (1-4), baeckenon B (5), and frutescones A, D-F (6-9), isolated from the leaves of Baeckea frutescens, were achieved in 9, 8, and 5 steps, respectively, in moderate to good yields (72-83%). The synthetic routes feature the Michael addition, oxidative [4 + 2] cycloaddition, and water-promoted Diels-Alder click reactions as the key steps. This study helped gain thorough mechanistic insights into the biosynthetic origins and provided a facile approach for the construction of a library of natural tasmanone-based meroterpenoid analogues. Moreover, compounds 1-9 show potent inhibitory effects against S. paratyphi and/or C. albicans with MIC values of 3.125-25 μg mL-1, and they could be promising lead molecules for the design of new antibiotic agents.

Anti-inflammatory acylphloroglucinol derivatives from hops (Humulus lupulus)

The polyphenol-enriched fraction of an ethanolic hops extract (Humulus lupulus) was separated to provide four acylphloroglucinol-glucopyranosides (1-4). 1-(2-Methylpropanoyl)phloroglucinol-glucopyranoside 1 has been isolated from hops before, whereas 1-(2-methylbutyryl)phloroglucinol-glucopyranoside 2, known as multifidol glucoside, and 1-(3-methylbutyryl)phloroglucinol- glucopyranoside 3 were found in hops for the first time. 5-(2-Methylpropanoyl) phloroglucinol-glucopyranoside 4 was identified as a new natural product. The compounds were tested for inhibition of COX-1 activity. The aglycon 5, obtained by acid hydrolysis of 1, was equally effective as phloroglucinol, with an IC50 of 3.8 μM. The inhibitory potential of the glucosides was 1 > 2 > 3 and decreased with increasing length of the acyl side chain. Compound 4 was about 2.5-fold less active than 1 (IC50: 23.7 and 58.7 μM, respectively).

Biosynthesis of the hyperforin skeleton in Hypericum calycinum cell cultures

Hyperforin is an important antidepressant constituent of Hypericum perforatum (St. John's wort). Cell cultures of the related species H. calycinum were found to contain the homologue adhyperforin and to a low extent hyperforin, when grown in BDS medium in

A greatly improved procedure for the synthesis of an antibiotic-drug candidate 2,4-diacetylphloroglucinol over silica sulphuric acid catalyst: multivariate optimisation and environmental assessment protocol comparison by metrics

Efforts toward the development of a straightforward greener Gram-scale synthesis of the antibiotic compound 2,4-diacetylphloroglucinol (DAPG) have been developed. This beneficial procedure was accomplished through the Friedel-Crafts acylation of phloroglucinol over inexpensive heterogeneous silica sulphuric acid (SSA) catalystviaultrasound-assisted (US) synthesis under solvent-free condition. The influences of various parameters such as temperature, catalyst loading, and reaction time on the reaction performance were analysed using a multivariate statistical modelling response surface methodology (RSM). A high yield ofDAPG(95%) was achieved at 60 °C after 15-20 min reaction with the presence of 10% (w/w)SSAas the catalyst. Column chromatography-free and a Gram scale-up reaction also exhibited the practical applicability of this newly developed protocol. TheSSAcatalyst was recovered and recycled up to 10 consecutive runs with no appreciable loss of activity. A plausible mechanism for the Friedel-Crafts acylation of phloroglucinol is proposed. Moreover, an environmental assessment has been carried out over this present method and compared with several established literature using the EATOS software and the Andraos algorithm to assess the consumption of the substrates, solvents, catalysts, and the production of coupled products or by-products. In addition, their energy consumptions were also determined. The data collected showed that the present method is the most promising one, characterised by the highest environmental impact profile against all the other reported methods. The physicochemical properties of the synthesisedDAPGwere assessed and exhibited reasonable oral bioavailability drug property as determined by Lipinski's rules.

Discovery and Biomimetic Synthesis of a Phloroglucinol-Terpene Adduct Collection from Baeckea frutescens and Its Biogenetic Origin Insight

A phloroglucinol-terpene adduct (PTA) collection consisting of twenty-four molecules featuring three skeletons was discovered from Baeckea frutescens. Inspired by its biosynthetic hypothesis, we synthesized this PTA collection by reductive activation of s

Biomimetic Syntheses of Callistrilones A-E via an Oxidative [3 + 2] Cycloaddition

Concise total syntheses of callistrilones A-E have been achieved from 7 and commercially available α-phellandrene (8). The synthetic strategy, which was primarily inspired by the biogenetic hypothesis, was enabled by an oxidative [3 + 2] cycloaddition fol

Hits-to-lead optimization of the natural compound 2,4,6-trihydroxy-3-geranyl-acetophenone (thga) as a potent lox inhibitor: Synthesis, structure-activity relationship (sar) study, and computational assignment

A new series of 2,4,6-trihydroxy-3-geranyl-acetophenone (tHGA) analogues were synthesized and evaluated for their lipoxygenase (LOX) inhibitory activity. Prenylated analogues 4a-g (half maximal inhibitory concentration (IC50) values ranging from 35 μM to 95 μM) did not exhibit better inhibitory activity than tHGA (3a) (IC50 value: 23.6 μM) due to the reduction in hydrophobic interaction when the alkyl chain length was reduced. One geranylated analogue, 3d, with an IC50 value of 15.3 μM, exhibited better LOX inhibitory activity when compared to tHGA (3a), which was in agreement with our previous findings. Kinetics study showed that the most active analogue (3e) and tHGA (3a) acted as competitive inhibitors. The combination of in silico approaches of molecular docking and molecular dynamic simulation revealed that the lipophilic nature of these analogues further enhanced the LOX inhibitory activity. Based on absorption, distribution, metabolism, excretion, and toxicity (ADMET) and toxicity prediction by komputer assisted technology (TOPKAT) analyses, all geranylated analogues (3a-g) showed no hepatotoxicity effect and were biodegradable, which indicated that they could be potentially safe drugs for treating inflammation.

Structural optimization and antibacterial evaluation of rhodomyrtosone B analogues against MRSA strains

Methicillin-resistant Staphylococcus aureus (MRSA) infections are well-known as a significant global health challenge. In this study, twenty-two congeners of the natural antibiotic rhodomyrtosone B (RDSB) were synthesized with the aim of specifically enhancing the structural diversity through modifying the pendant acyl moiety. The structure-activity relationship study against various MRSA strains revealed that a suitable hydrophobic acyl tail in the phloroglucinol scaffold is a prerequisite for antibacterial activity. Notably, RDSB analogue 11k was identified as a promising lead compound with significant in vitro and in vivo antibacterial activities against a panel of hospital mortality-relevant MRSA strains. Moreover, compound 11k possessed other potent advantages, including breadth of the antibacterial spectrum, rapidity of bactericidal action, and excellent membrane selectivity. The mode of action study of compound 11k at the biophysical and morphology levels disclosed that 11k exerted its MRSA bactericidal action by membrane superpolarization resulting in cell lysis and membrane disruption. Collectively, the presented results indicate that the novel modified RDSB analogue 11k warrants further exploration as a promising candidate for the treatment of MRSA infections.

Synthesis and anti-inflammatory activities of phloroglucinol-based derivatives

The natural product phloroglucinol-based derivatives representing monoacyl-, diacyl-, dimeric acyl-, alkylated monoacyl-, and the nitrogen-containing alkylated monoacylphloro- glucinols were synthesized and evaluated for inhibitory activities against the inflammatory mediators such as inducible nitric oxide synthase (iNOS) and nuclear factor kappaB (NF-κB). The diacylphloroglucinol compound 2 and the alkylated acylphloroglucinol compound 4 inhibited iNOS with IC50 values of 19.0 and 19.5 μM, respectively, and NF-κB with IC50 values of 34.0 and 37.5 μM, respectively. These compounds may serve as leads for the synthesis of more potent anti-inflammatory compounds for future drug discovery.