69097-99-0

Basic information

• Product Name: (2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone
• Synonyms: (2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone;5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone;rac-Hesperetin;5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
• CAS NO: 69097-99-0
• Molecular Formula: C16H14O6
• Molecular Weight: 302.27876
• Mol File: 69097-99-0.mol
• Article Data: 42

Chemical Properties

• Melting Point: 227-232°C
• Boiling Point: 586.2±50.0 °C(Predicted)
• Appearance: /
• Density: 1.458±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: ethanol: soluble50mg/mL, clear to almost clear, colorless to sli
• PKA: 7.49±0.40(Predicted)
• CAS DataBase Reference: (2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone(69097-99-0)
• EPA Substance Registry System: (2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone(69097-99-0)

Safety Data

• WGK Germany: 2
• Hazardous Substances Data: 69097-99-0(Hazardous Substances Data)

Usage

Description

(2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone is a naturally occurring flavonoid compound that possesses a unique structure and a range of biological activities. It is characterized by the presence of multiple hydroxyl and methoxy groups, which contribute to its potential therapeutic properties.

Uses

Used in Pharmaceutical Industry:
(2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone is used as a pharmaceutical agent for its potential cytotoxic effects on cancer cells. Studies have shown that hesperetin, a related flavonoid, has been used as a standard in research involving the cytotoxic effect of hesperetin on doxorubicin-resistant MCF-7 cells using enzyme-linked immunosorbent assay (ELISA) technique. This suggests that (2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone may also exhibit similar cytotoxic properties and could be a promising candidate for the development of anticancer drugs.
Additionally, the compound's unique structure and functional groups may allow it to interact with various biological targets, making it a potential candidate for the treatment of other diseases and conditions. Further research is needed to fully explore its therapeutic potential and optimize its use in the pharmaceutical industry.

Biochem/physiol Actions

Dietary flavanone with chemopreventive effect.

Upstream product

• 520-26-3 hesperidin 
• 161713-86-6 4^G-α-D-glucopyranosyl hesperidin 
• 520-33-2 hesperetin 
• 520-33-2 (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 
• 64726-90-5 (2S)-7-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one 
• 6157-13-7 1-[2-hydroxy-4,6-bis-(tetra-O-acetyl-β-D-glucopyranosyloxy)-phenyl]-ethanone 
• 621-59-0 isovanillin 
• 107-21-1 ethylene glycol 
• 6198-24-9 2',4'-bis-β-D-glucopyranosyloxy-3,6'-dihydroxy-4-methoxy-trans-chalcone 
• 108-73-6 3,5-dihydroxyphenol 
• 49806-44-2 3-ethoxycarbonyloxy-4-methoxy-cinnamoyl chloride 
• 75679-30-0 Hesperetin chalcone 
• 485-80-3 S-adenosyl-L-methionine 
• 552-58-9 eriodictyol 

Downstream Products

• 70987-96-1 5-hydroxy-3′4′7-trimethoxy flavanone 
• 6274-73-3 (S)-5,7-diacetoxy-2-(3-acetoxy-4-methoxy-phenyl)-chroman-4-one 
• 6033-54-1 (-)-hesperetin oxime 
• 75917-11-2 5-hydroxy-6,3',4'-trimethoxyflavanone 
• 211255-69-5 5,7,3'-trihydroxydihydroquercetin 3-acetate 4'-(methyl ether) 
• 3162-05-8 3',5,7-triacetoxy-4'-methoxyflavone 
• 6274-73-3 3',5,7-triacetoxy-4'-methoxyflavanone 
• 6033-54-1 (+/-)-hesperetin oxime 
• 128373-93-3 Acetic acid 5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-4-oxo-chroman-7-yl ester 
• 128373-92-2 Acetic acid 5-(5,7-dihydroxy-4-oxo-chroman-2-yl)-2-methoxy-phenyl ester 
• 80514-56-3 3',5'-dihydroxy-4'-methoxy-7(3-azido-3-carboxypropoxy)flavanone 
• 2500-68-7 5,7,3'-trihydroxy-4'-methoxyl flavanone 7-O-glucoside 
• 675139-61-4 Hesperetin 7-O-sulfate 
• 945038-48-2 Hesperetin 3'-O-sulfate 

Relevant articles and documents

Discovery of Novel Bacterial Chalcone Isomerases by a Sequence-Structure-Function-Evolution Strategy for Enzymatic Synthesis of (S)-Flavanones

Chalcone isomerase (CHI) is a key enzyme in the biosynthesis of flavonoids in plants. The first bacterial CHI (CHIera) was identified from Eubacterium ramulus, but its distribution, evolutionary source, substrate scope, and stereoselectivity are still unclear. Here, we describe the identification of 66 novel bacterial CHIs from Genbank using a novel Sequence-Structure-Function-Evolution (SSFE) strategy. These novel bacterial CHIs show diversity in substrate specificity towards various hydroxylated and methoxylated chalcones. The mutagenesis of CHIera according to the substrate binding models of these novel bacterial CHIs resulted in several variants with greatly improved activity towards these chalcones. Furthermore, the preparative scale conversion catalyzed by bacterial CHIs has been performed for five chalcones and revealed (S)-selectivity with up to 96 % ee, which provides an alternative biocatalytic route for the synthesis of (S)-flavanones in high yields.

Enhanced antioxidant, anti-inflammatory and α-glucosidase inhibitory activities of citrus hesperidin by acid-catalyzed hydrolysis

Hesperidin hydrolysates (HHS) was produced by the hydrolysis of hesperidin (HDN) in previous studies. The potential components in HHS were identified by LC-MS, and minor components (MCS) in HHS were isolated. Antioxidant activities by radical-scavenging capacities, reducing capacity and β-carotene-linoleate assay, anti-inflammatory effects by inhibiting NO production of RAW 264.7 cells, and α-glucosidase inhibitory effects of HDN, HHS, MCS and henperetin (HTN) were investigated in present study. HHS showed higher radical scavenging activities, higher reducing capacity, and higher inhibitory activity in the β-carotene-linoleate assay than HDN. HHS inhibited the production of NO and pro-inflammatory cytokines of RAW 264.7 cells more strongly than HDN. HHS also intensively inhibited α-glucosidase activity whereas HDN showed little activity. In addition, the effects of MCS on above activities showed it play a synergistic part with HTN. This work suggested that hydrolyzation of HDN enhance the activities, and provided valuable information on effective utilization of HDN.

Synthesis of 5-Hydroxy-3′,4′,7-trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2-Mediated Anticancer Drug Resistance

3′,4′,7-Trimethoxyflavone (TMF) has been reported to show a potent reversal effect on drug resistance mediated by breast cancer resistance protein (BCRP)/ATP-binding cassette subfamily G member 2 (ABCG2). In this study, we designed and synthesized five derivatives with either a hydroxy group or a fluorine atom at C-5 and several kinds of capping moiety at the C-7 hydroxy group, on the same 3′,4′-dimethoxy-substituted flavone skeleton. We subsequently evaluated the efficacies of these compounds against BCRP-expressing human leukaemia K562/BCRP cells. Reversal of drug resistance was expressed as the concentration of compound causing a twofold reduction in drug sensitivity (RI50). Of the synthesized compounds, the reversal effect of 5-hydroxy-3′,4′,7-trimethoxyflavone (HTMF, RI50 7.2 nm) towards 7-ethyl-10-hydroxycamptothecin (SN-38) was stronger than that of TMF (RI50 18 nm). Fluoro-substituted 5-fluoro-3′,4′,7-trimethoxyflavone (FTMF, RI50 25 nm) and monoglycosylated 7-(β-glucosyloxy)-5-hydroxy-3′,4′-dimethoxyflavone (GOHDMF, 91 nm) also exhibited reversal effects, whereas the di- and triglycoside derivatives did not. TMF, HTMF and FTMF at 0.01–10 μm upregulated the K562/BCRP cellular accumulation of Hoechst 33342 nuclear staining dye. In addition, western blotting revealed that treatment of K562/BCRP cells with 0.1 μm TMF, HTMF or FTMT suppressed the expression of BCRP. HTMF showed the strongest inhibition of BCRP-mediated efflux and suppression of BCRP expression of the three effective synthesized flavones.