1509-06-4

Usage

Uses

Used in Pharmaceutical Applications:
2',4',6'-Trihydroxy-3'-methylbutyrophenone is used as a therapeutic agent for its antioxidant, anti-inflammatory, and neuroprotective properties. It is particularly beneficial in the treatment of conditions where oxidative stress plays a significant role, such as neurodegenerative diseases and inflammatory disorders.
Used in Cosmetic Applications:
In the cosmetic industry, 2',4',6'-Trihydroxy-3'-methylbutyrophenone is used as an active ingredient for its antioxidant activity, which helps protect the skin from oxidative damage and promotes overall skin health. Its inclusion in skincare products can contribute to a more youthful and radiant appearance.
Used in Food Industry:
2',4',6'-Trihydroxy-3'-methylbutyrophenone is used as a natural preservative or additive in the food industry due to its antioxidant properties. It can help extend the shelf life of food products and maintain their freshness and quality, making it a valuable component in food formulations.

Upstream product

• 88-03-9 2,4,6-trihydroxytoluene 
• 141-75-3 butyryl chloride 
• 7647-01-0 hydrogenchloride 
• 109-74-0 propyl cyanide 
• 60-29-7 diethyl ether 
• 108-73-6 3,5-dihydroxyphenol 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 6099-90-7 1,3,5-Trihydroxybenzene dihydrate 
• 106-31-0 butanoic acid anhydride 
• 14107-97-2 2,4,6-trimethoxytoluene 
• 830-79-5 2,4,6-trimethoxybenzaldehyde 
• 621-23-8 1,2,3-trimethoxybenzene 
• 5556-54-7 bis(2,4,6-trihydroxyphenyl)methane 
• 39828-33-6 2,4,6-Trihydroxy-3-methyl-benzoesaeure-methylester 

Downstream Products

• 3761-64-6 flavaspiridic acid AB 
• 3773-25-9 flavaspidic acid PB 
• 114-42-1 2-butyryl-6-(3-butyryl-2,4,6-trihydroxy-5-methyl-benzyl)-3,5-dihydroxy-4,4-dimethyl-cyclohexa-2,5-dienone 

Relevant academic research and scientific papers

Synthetic method of pilosin B and intermediate pseudomonophenols thereof

The invention discloses a method for synthesizing pilosin B and intermediate pseudomonophenols thereof. The synthesis method of the pseudo-sheep equol comprises the step E. Step F and Step g. The synthetic method of the pilosin B provided by the invention is prepared by the following steps H, step J, preparation of the pseudomonophenols synthesized by the above method, and preparation of the pseudomonophenols synthesized by the method in step I. In step E, the novel amino protecting reagent with good reaction with the phenolic hydroxyl group is used as a protecting reagent, the phenol hydroxyl group of each intermediate in the intermediate molecule fragment a synthesis process is selectively protected, the reagent types are reduced and the use of toxic reagents such as benzyl chloride and the like is avoided.

Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment

Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.

Synthesis and antibiotic activity of novel acylated phloroglucinol compounds against methicillin-resistant Staphylococcus aureus

The rise in antibiotic resistance among pathogenic microorganisms has created an imbalance in the drugs available for treatment, in part due to the slow development of new antibiotics. Cystic fibrosis (CF) patients are highly susceptible to antibiotic-resistant pathogens, including methicillin-resistant Staphylococcus aureus (MRSA). Phloroglucinols and related polyketide natural products have demonstrated antimicrobial activity against a number of Gram-positive bacteria including S. aureus. In this study, we investigated a series of acylated phloroglucinol derivatives to determine their potential as lead compounds for the design of novel therapeutics. To assess the activity of these compounds, we determined the minimum inhibitory and bactericidal concentration (MIC and MBC, respectively), the minimum biofilm inhibitory and biofilm eradication concentration (MBIC and MBEC, respectively), and evaluated hemolytic activity, as well as their interaction with clinically relevant antibiotics. Of the 12 compounds tested against MRSA and methicillin-susceptible strains, four showed MIC values ranging from 0.125 to 8 μg ml?1 and all of them were bactericidal. However, none of the compounds were able to eradicate biofilms at the concentrations tested. Three of the four did not display hemolytic activity under the conditions tested. Further studies on the interactions of these compounds with clinically relevant antibiotics showed that phlorodipropanophenone displayed synergistic activity when paired with doxycycline. Our results suggest that these acylated phloroglucinols have potential for being further investigated as antibacterial leads.

Novel diphenylmethyl compounds having mycobacterium tuberculosis inhibitory activity

The invention relates to novel diphenylmethyl derivatives having mycobacterium tuberculosis inhibitory activity and a preparation method thereof and particularly relates novel diphenylmethyl derivatives having activity for inhibiting replicative and non-replicating mycobacterium tuberculosis and a preparation method thereof. In particular, the invention relates to compounds shown in the formula (I) or all possible isomers, prodrugs, pharmaceutically acceptable salts, solvates or hydrates thereof, wherein the variables are as described in the specification. The invention also relates to the preparation method of the compounds and their pharmaceutical compositions and a use of the compounds in preparation of drugs for treating mycobacterium tuberculosis infection-caused diseases.

Derivatives of Natural Product Agrimophol as Disruptors of Intrabacterial pH Homeostasis in Mycobacterium tuberculosis

This article reports the rational medicinal chemistry of a natural product, agrimophol (1), as a new disruptor of intrabacterial pH (pHIB) homeostasis in Mycobacterium tuberculosis (Mtb). Through the systematic investigation of the structure-activity relationship of 1, scaffold-hopping of the diphenylmethane scaffold, pharmacophore displacement strategies, and studies of the structure-metabolism relationship, a new derivative 5a was achieved. Compound 5a showed 100-fold increased potency in the ability to reduce pHIB to pH 6.0 and similarly improved mycobactericidal activity compared with 1 against both Mycobacterium bovis-BCG and Mtb. Compound 5a possessed improved metabolic stability in human liver microsomes and hepatocytes, lower cytotoxicity, higher selectivity index, and similar pKa value to natural 1. This study introduces a novel scaffold to an old drug, resulting in improved mycobactericidal activity through decreasing pHIB, and may contribute to the critical search for new agents to overcome drug resistance and persistence in the treatment of tuberculosis.

Total synthetic method of natural product pseudoaspidinol

The invention relates to a total synthetic method of a natural product pseudoaspidinol, belonging to the technical field of organic chemistry. The method comprises the steps of carrying out Vilsmeier-Haaucf reaction on economic and easily-available phloroglucinol dehydrate so as to obtain aldehyde-base phloroglucinol, carrying out Clemmensen reduction so as to obtain methyl phloroglucinol, carrying out Friedel-Crafts acylation so as to obtain lysine butyrylation methyl phloroglucinol, carrying out selective protection through ester groups, and carrying out methylation and deprotection, so as to obtain pseudoaspidinol. The total synthetic method has the beneficial effects that the total synthesis yield of pseudoaspidinol is increased at the total yield of 51%, the raw materials are economicand easily available, the operation is simple, the yield is relatively high, and a large number of raw materials are provided for the biological activity research of pseudoaspidinol.

A natural product yellow filicic acid BB of full-synthesis method

The invention relates to a natural product yellow filicic acid BB of full-synthesis method, which belongs to the technical field of organic chemistry. The invention from the economic and easy to synthesize the phloroglucinol proceed double-acylated phloroglucinol, then after iodine methane-to-carbon double methylation, removing monomolecular acyl got the midbody 3; to phloroglucinol as raw materials, acetate acylation to obtain the aldehyde phloroglucinol, reduction of the aldehyde is methyl, then acylated to obtain intermediate 6; the two fragments obtained through the Eschenmoser's salt combined yellow filicic acid BB. In the method 42% overall yield of yellow filicic acid improves the BB fully synthetic yield, raw material economy are easy, simple operation, high yield, and suitable for production, may be its biological activity study provide a large number of raw materials.

Antifungal agents: Design, synthesis, antifungal activity and molecular docking of phloroglucinol derivatives

Pseudoaspidinol is a phloroglucinol derivative with Antifungal activity and is a major active component of Dryopteris fragrans. In our previous work, we studied the total synthesis of pseudoaspidinol belonging to a phloroglucinol derivative and investigated its antifungal activity as well as its intermediates. However, the results showed these compounds have low antifungal activity. In this study, in order to increase antifungal activities of phloroglucinol derivatives, we introduced antifungal pharmacophore allylamine into the methylphloroglucinol. Meanwhile, we remained C1–C4 acyl group in C-6 position of methylphloroglucinol using pseudoaspidinol as the lead compound to obtain novel phloroglucinol derivatives, synthesized 17 compounds, and evaluated antifungal activities on Trichophyton rubrum and Trichophyton mentagrophytes in vitro. Molecular docking verified their ability to combine the protein binding site. The results indicated that most of the compounds had strong antifungal activity, in which compound 17 were found to be the most active on Trichophyton rubrum with Minimum Inhibitory Concentration (MIC) of 3.05 μg/mL and of Trichophyton mentagrophytes with MIC of 5.13 μg/mL. Docking results showed that compounds had a nice combination with the protein binding site. These researches could lay the foundation for developing antifungal agents of clinical value.

Dryopteris fragrans phloroglucinol compound flavaspidic acid BB and antibacterial application thereof

The invention relates to the technical field of medicine and discloses an antibacterial application of a Dryopteris fragrans phloroglucinol compound flavaspidic acid BB. The invention provides the flavaspidic acid BB obtained by the chemical synthesis method. The flavaspidic acid BB has good antibacterial effects, effectively fills in the application deficiency of the antibacterial natural compound and provides an effective antibacterial solution for drug-resistant bacteria. The experimental results show that the compound has a strong antibacterial effect and good curative effects especially on drug-resistant bacteria.