1509-06-4

Basic information

• Product Name: 2',4',6'-Trihydroxy-3'-methylbutyrophenone
• Synonyms: 2',4',6'-Trihydroxy-3'-methylbutyrophenone
• CAS NO: 1509-06-4
• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23
• Mol File: 1509-06-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 154-155 °C
• Boiling Point: 356.1±37.0 °C(Predicted)
• Appearance: /
• Density: 1.269±0.06 g/cm3(Predicted)
• PKA: 7.77±0.50(Predicted)
• CAS DataBase Reference: 2',4',6'-Trihydroxy-3'-methylbutyrophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2',4',6'-Trihydroxy-3'-methylbutyrophenone(1509-06-4)
• EPA Substance Registry System: 2',4',6'-Trihydroxy-3'-methylbutyrophenone(1509-06-4)

Safety Data

• Hazardous Substances Data: 1509-06-4(Hazardous Substances Data)

Usage

General Description

2',4',6'-Trihydroxy-3'-methylbutyrophenone, also known as acarotene, is a natural compound found in the leaves of the plant acaroid resin. It is a phenolic derivative with three hydroxyl groups and a methylbutyrophenone side chain. Acarotene has been identified as a potent antioxidant and has been shown to exhibit anti-inflammatory and neuroprotective properties in various studies. Its antioxidant activity makes it a promising candidate for use in pharmaceutical and cosmetic products, as it can help protect against oxidative damage and promote overall skin health. Additionally, acarotene has potential applications in the food industry, as it may serve as a natural preservative or additive due to its antioxidant properties.

Upstream product

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

Downstream Products

• 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 articles and documents

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.

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.

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.