1088-08-0

Basic information

• Product Name: 2'',4'',6''-TRIHYDROXYDIHYDROCHALCONE
• Synonyms: Propiophenone,2',4',6'-trihydroxy-3-phenyl- (7CI,8CI); 2',4',6'-Trihydroxydihydrochalcone;2',4',6'-Trihydroxyhydrochalcone;3-Phenyl-1-(2,4,6-trihydroxyphenyl)-1-propanone
• CAS NO: 1088-08-0
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.26926
• Product Categories: Chalcones
• Mol File: 1088-08-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2'',4'',6''-TRIHYDROXYDIHYDROCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2'',4'',6''-TRIHYDROXYDIHYDROCHALCONE(1088-08-0)
• EPA Substance Registry System: 2'',4'',6''-TRIHYDROXYDIHYDROCHALCONE(1088-08-0)

Safety Data

• Hazardous Substances Data: 1088-08-0(Hazardous Substances Data)

Usage

Uses

Used in Food and Beverage Industry:
2'',4'',6''-Trihydroxydihydrochalcone is used as a sugar substitute in foods and beverages for its strong sweetening properties and low calorie content. It provides a healthier alternative to traditional sugars, helping to reduce calorie intake and manage blood sugar levels.
Used in Natural Medicine:
2'',4'',6''-Trihydroxydihydrochalcone is used in natural medicine due to its potential therapeutic effects. Its antioxidant properties can help protect the body from oxidative stress and support overall health. Additionally, its anti-inflammatory properties may contribute to reducing inflammation and promoting healing.
Used in Food Science Research:
2'',4'',6''-Trihydroxydihydrochalcone is a widely researched chemical compound in the field of food science. Its unique properties and potential health benefits make it an attractive subject for further exploration and development of new applications in food products and supplements.

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 645-59-0 dihydrocinnamonitrile 
• 645-45-4 hydrocinnamic acid chloride 
• 102-93-2 3-phenylpropionamide 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 
• 501-52-0 3-Phenylpropionic acid 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 169132-91-6 (E)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)-3-phenylprop-2-en-1-one 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 100-52-7 benzaldehyde 
• 1122-91-4 4-bromo-benzaldehyde 
• 82451-30-7 2',4',6'-trihydroxychalcone 
• 128837-25-2 1-[2,4-bis(ethoxymethoxy)-6-hydroxyphenyl]ethan-1-one 

Downstream Products

• 906433-07-6 (+/-) linderatin 
• 94530-80-0 linderatin 
• 120217-41-6 neolinderachalcone 
• 135383-81-2 3′-formyl-2′,4′,6′-trihydroxydihydrochalcone 
• 1266170-07-3 1-[3-(β-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-3-phenylpropan-1-one 
• 34328-57-9 2,2,4-trimethyl-6-(1-oxo-3-phenylpropyl)cyclohexane-1,3,5-trione 
• 1235289-00-5 2',4',6'-trihydroxy-3',5'-di-C-β-D-glucopyranosyldihydrochalcone 
• 70155-33-8 1-(2,4,6-trihydroxy-3-methyl)phenyl-3-phenyl-1-propanone 
• 10499-26-0 grandiflorone 

Relevant articles and documents

Hydrogen-bonded rotamers of 2′,4′,6′-trihydroxy-3′-formyldihydrochalcone, an intermediate in the synthesis of a dihydrochalcone from Leptospermum recurvum

Synthesis of 2′,4′,6′-trihydroxy-3′-methyldihydrochalcone, isolated as a natural product for the first time (ex Leptospermum recurvum), proceeds through 2′,4′,6′-trihydroxy-3′-formyldihydrochalcone. Two stable rotamers of this formyl derivative have been

DIHYDROCHALCONES FROM LINDERA UMBELLATA

Two dihydrochalcones, 2',6'-dihydroxy-4'-methoxydihydrochalcone and 2',4',6'-trihydroxydihydrochalcone have been isolated form leaves of Lindera umbellata.Key words: Lindera umbellata; Lauraceae; 2',6'-dihydroxy-4'-methoxydihydrochalcone; 2',4',6'-trihydr

Design, synthesis and antiproliferative activity evaluation of fluorine-containing chalcone derivatives

A series of new chalcones containing fluoro atom at B ring have been designed, synthesized, and evaluated to be antiproliferative activity against a panel of human tumor cell lines. Some of the analogs (8, 9, 12, 45, 46 and 48) displayed powerful antiproliferative effects to certain human tumor cells, but all of them were devoid of any cytotoxicity towards the normal HEK 293. Acridine orange staining data supported that the cytotoxic and antiproliferative effects of the synthesized analogs on tumor cells are mediated through apoptosis. The compounds 12 and 46 manifested concentration-dependent antiproliferative activity in human hepatocellular carcinoma cell lines using an xCELLigence assay. The structures and antiproliferative activity relationship were further supported by in silico molecular docking study of the compounds against tubulin protein which suggests our compounds interference to cell division. Communicated by Ramaswamy H. Sarma.

Quinoid dihydrochalcone dicarbonyl glycoside compound with glucose on A ring, preparation method and neuroprotective activity thereof

The invention discloses a class of quinoid dihydrochalcone C-glycoside compounds with glucose on a ring A, a preparation method and anti-cerebral ischemia injury activity thereof, wherein the compoundhas a structure represented by a general formula (I). The preparation method of the compound comprises the following steps: (1) synthesizing a 2,4,6-trihydroxy dihydrochalcone compound; (2) synthesizing a 2,4,6-trihydroxy-3,5-diglucosyl dihydrochalcone C-glycoside compound; and (6) synthesizing a class of quinoid dihydrochalcone C-glycoside compound with glucose in the A ring. The compound disclosed by the invention is simple in preparation method and has a remarkable effect of resisting cerebral ischemia injury.

Arylpropionyl-triketone antibacterial agents

The invention provides a compound of formula (I): or a salt thereof, wherein R1-R5 have any of the values described in the specification, as well as compositions comprising a compound of formula (I). The compounds are useful as RNA p

Photodegradation of Myrigalone A, an Allelochemical from Myrica gale: Photoproducts and Effect of Terpenes

This study investigated the environmental fate of myrigalone A, a light absorbing natural herbicide found on leaves and fruits of Myrica gale. Myrigalone A was irradiated in water and as a dry solid deposit to simulate reactions on leaves, alone and in the presence of the terpenes generated by Myrica gale. The phototransformation was fast (t1/2 = 35 min in water). Analyses by liquid chromatography coupled to high resolution orbitrap electrospray mass spectrometry (MS) and gas chromatography-MS revealed the formation of 11 photoproducts in water and solid and 9 in gaseous phase. Some were detected in the leaf glands and oil covering the fruits of Myrica gale, which suggested that photodegradation occurred in the field. Moreover, myrigalone A photoinduced the oxidation of terpenes that in turn protected it against photolysis. This highlights the need for additional research on the effect of terpenes on the photodegradation of pesticides on vegetation.

Base-catalyzed oxidative dearomatization of multisubstituted phloroglucinols: An easy access to C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives

An efficient and simple method for the protecting group-free synthesis of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone has been firstly established. This method is compatible with various functional groups, such as benzyl and phenethyl groups, affording a range of C-glucosyl 3,5,6-trihydroxycyclohexa-2,4-dienone derivatives.

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.

Targeting type 2 diabetes with c-glucosyl dihydrochalcones as selective sodium glucose co-transporter 2 (sglt2) inhibitors: Synthesis and biological evaluation

Inhibiting glucose reabsorption by sodium glucose co-transporter proteins (SGLTs) in the kidneys is a relatively new strategy for treating type 2 diabetes. Selective inhibition of SGLT2 over SGLT1 is critical for minimizing adverse side effects associated with SGLT1 inhibition. A library of C-glucosyl dihydrochalcones and their dihydrochalcone and chalcone precursors was synthesized and tested as SGLT1/SGLT2 inhibitors using a cell-based fluorescence assay of glucose uptake. The most potent inhibitors of SGLT2 (IC50 = 9.23 nM) were considerably weaker inhibitors of SGLT1 (IC50 = 10.19 μM). They showed no effect on the sodium independent GLUT family of glucose transporters, and the most potent ones were not acutely toxic to cultured cells. The interaction of a C-glucosyl dihydrochalcone with a POPC membrane was modeled computationally, providing evidence that it is not a pan-assay interference compound. These results point toward the discovery of structures that are potent and highly selective inhibitors of SGLT2.

Structure-activity relationships and optimization of acyclic acylphloroglucinol analogues as novel antimicrobial agents

Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to global public health, because it exhibits resistance to existing antibiotics and therefore high rates of morbidity and mortality. In this study, twenty-one natural product-based acylphloroglucinol congeners were synthesized, which possessed different side chains. Antibacterial screening against MRSA strains revealed that acyl moiety tailoring is a prerequisite for the antibacterial activity. Moreover, the lipophilicity, rather than the magnitude of the hydrophobic acyl tail dominates variability in activity potency. Compound 11j was identified as a promising lead for the generation of new anti-MRSA drug development. It was discovered by optimization of the side chain length in light of the potency, the breadth of the antibacterial spectrum, the rate of bactericidal action, as well as the membrane selectivity. Compound 11j exerted profound in?vitro antibacterial activity against the MRSA strain (JCSC 2172), and its MIC was 3-4 orders of magnitude lower than that of vancomycin. A preliminary mode of action study of compound 11j at the biophysical and morphology levels disclosed that the mechanism underlying its anti-MRSA activity included membrane depolarization and, to a lesser extent, membrane disruption and cell lysis.