6665-72-1

Usage

Also known as

Helichrysetin
Naturally occurring flavonoid compound found in various plants, including Helichrysum species

Properties

Potential antioxidant
Anti-inflammatory
Anticancer
Neuroprotective
Therapeutic agent for skin conditions
Chemopreventive agent against certain types of cancer
Potential in the management of metabolic syndrome and diabetes

Specific Health Benefits

Neuroprotective effects
Potential application in the treatment of neurodegenerative diseases
Therapeutic application for skin conditions
Chemopreventive agent against cancer
Potential in the management of metabolic syndrome and diabetes

InChI:InChI=1/C16H12O4/c1-19-11-7-5-10(6-8-11)15-9-13(18)16-12(17)3-2-4-14(16)20-15/h2-9,17H,1H3

Upstream product

• 6665-67-4 5,4'-dihydroxyflavone 
• 77-78-1 dimethyl sulfate 
• 105285-09-4 4,6'-dimethoxy-2'-hydroxychalcone 
• 58124-15-5 2',6'-bis(4-methoxybenzoyloxy)acetophenone 
• 699-83-2 2,6-dihydroxylacetophenone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 6697-63-8 5,4'-Dimethoxyflavone 
• 78646-28-3 2′-hydroxy-6′-methoxymethoxyacetophenone 
• 768-60-5 4-methoxyphenylacetylen 
• 794-94-5 p-Methoxybenzoic anhydride 
• 742079-31-8 2-(4-benzyloxy-phenyl)-5-methoxy-chromen-4-one 
• 106848-87-7 4'-hydroxy-5-methoxyflavone 
• 105285-09-4 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 

Downstream Products

• 872826-17-0 5,8-dihydroxy-2-(4-methoxy-phenyl)-chromen-4-one 

Relevant academic research and scientific papers

Unified Approach to (Thio)chromenones via One-Pot Friedel-Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones

A facile synthetic method to chromenones and thiochromenones has been developed using a one-pot Friedel-Crafts acylation of alkynes with suitably substituted benzoyl chlorides. This unified approach to (thio)chromenones is readily applicable to aryl- and alkylalkynes where the stereochemically well-defined β-chlorovinyl ketone intermediates undergo distinctively different cyclization pathways. The ready availability of both starting materials, alkynes and benzoyl chlorides, coupled with the experimental simplicity makes the current synthetic method to (thio)chromenones fast, efficient, and practical.

Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice.

Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr 3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3′,4′- dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production.

3-Aroyl-5-hydroxyflavones: Synthesis and transformation into aroylpyrazoles

Treatment of 3-aroyl-5-benzyloxyflavones 4a-e with hydrazine afforded 3,5-diaryl-4-(2-benzyloxy-6-hydroxybenzoyl)pyrazoles 5a-e, together with 4-aroyl-5-aryl-3-(2-benzyloxy-6- hydroxyphenyl)pyrazoles 6a-e as minor products. The structures of all new compounds have been established by extensive NMR studies and the reaction mechanisms are discussed. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

A one-step synthesis of 5-hydroxyflavones

5-hydroxy flavones were prepared in one step starting from 2,6- dihydroxyacetophenone. The latter was treated with an aroyl chloride in the presence of an excess of potassium carbonate to afford 5-hydroxyflavones.

3-Aroyl-5-hydroxyflavones: Synthesis and mechanistic studies by mass spectrometry

The synthesis and mass spectra of three 3-aroyl-5-hydroxflavones are reported. The interpretation of the mechanistic pathways for the fragmentation of the metastable molecular ions of these compounds was achieved through the analysis of their mass-analysed ion kinetic energy (MIKE) spectra and of the B2/E spectra of a few fragment ions. Labelling of the hydroxyl proton with deuterium and the analysis of the MIKE spectra of a model compound with chlorine atoms in the 2',6'- and 2',6'-positions led to a mechanism for the losses of OH. and HCO. which involves hydrogen migration from the 2'- or 6'-position to the 6-carbonyl oxygen atom. A mechanism for the loss of a neutral molecule of anisole from the molecular ion of the 3-aroyl-5-hydroxyflavone with a methoxyl group in the 4'- and 4'-positions is also suggested. For the flavones with hydrogen or chlorine substituents at these positions, loss of a phenyl (or chlorophenyl) radical occurs instead.

Synthesis and Characterization of Ruthenium(II) Complexes of 5-Hydroxyflavones

Bis(dimethyl sulfoxide)bis(flavonato)ruthenium(II) complexes, RuL2(DMSO)2, were synthesized by the reaction of dichlorotetrakis(dimethyl sulfoxide)ruthenium(II) with the sodium salts of 5-hydroxyflavone, 5-hydroxy-4'-methoxyflavone, and 5-hydroxy-3',4',5'