480-43-3

Basic information

• Product Name: ISOSAKURANETIN
• Synonyms: 5,7-DIHYDROXY-4'-METHOXYFLAVANONE;ISOSAKURANETIN;(S)-2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone;ISOSAKURANETIN(P);5,7-DIHYDROXY-4''-METHOXYFLAVANONE hplc;ISOSAKURANETIN WITH HPLC;(2S)-5,7-Dihydroxy-4'-methoxyflavanone;(S)-2,3-Dihydro-2-(4-methoxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
• CAS NO: 480-43-3
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28
• EINECS: 207-551-8
• Product Categories: Flavanones;Flavonoids
• Mol File: 480-43-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 193-194°C
• Boiling Point: 539.2oC at 760 mmHg
• Flash Point: 205.6oC
• Appearance: /
• Density: 1.37g/cm3
• Vapor Pressure: 3.06E-12mmHg at 25°C
• Refractive Index: 1.637
• PKA: 7.50±0.40(Predicted)
• CAS DataBase Reference: ISOSAKURANETIN(CAS DataBase Reference)
• NIST Chemistry Reference: ISOSAKURANETIN(480-43-3)
• EPA Substance Registry System: ISOSAKURANETIN(480-43-3)

Safety Data

• Statements: 22
• Safety Statements: 22-45
• Hazardous Substances Data: 480-43-3(Hazardous Substances Data)

Usage

Uses

(S)-Isosakuranetin, is a flavanone flavonoid which can be found in the fruit of Citrus bergamia.

Definition

ChEBI: A dihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5 and 7 and a methoxy group at position 4' (the 2S stereoisomer).

InChI:InChI=1/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

Upstream product

• 491-69-0 (2S)-poncirenin 
• 108-73-6 3,5-dihydroxyphenol 
• 42996-84-9 p-methoxycinnamoyl chloride 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 77-78-1 dimethyl sulfate 
• 123-11-5 4-methoxy-benzaldehyde 
• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 327096-49-1 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 
• 10236-47-2 naringin 
• 186581-53-3 diazomethane 
• 137225-57-1 (E)-3-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one 

Downstream Products

• 1181215-24-6 8-geranylisosakuranetin 
• 76172-68-4 3-(4-methoxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one 
• 29424-96-2 naringenin-4',7-dimethyl ether 
• 117894-08-3 5,7-diacetoxy-2-(4-methoxy-phenyl)-chroman-4-one 
• 108-73-6 3,5-dihydroxyphenol 
• 100-09-4 4-methoxybenzoic acid 
• 480-44-4 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one 

Relevant articles and documents

Design, synthesis, and cholinesterase inhibition assay of liquiritigenin derivatives as anti-Alzheimer's activity

The marine environment is a rich resource for discovering functional materials, and seaweed is recognized for its potential use in biology and medicine. Liquiritigenin has been isolated and identified from Sargassum pallidum. To find new anti-Alzheimer's activity, we designed and synthesized thirty-two 7-prenyloxy-2,3-dihydroflavanone derivatives (3a-3p) and 5-hydroxy-7-prenyloxy-2,3-dihydro-flavanone derivatives (4a-4p) as cholinesterases inhibitors based on liquiritigenin as the lead compound. Inhibition screening against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) indicated that all synthesized compounds possessed potent AChE inhibitory activity and moderated to weak BuChE inhibitory activity in vitro. Kinetic studies demonstrated that compound 4o inhibited AChE via a dual binding site ability. In addition, all compounds displayed the radical scavenging effects. Finally, the molecular docking simulation of 4o in AChE active site displayed good agreement with the obtained the pharmacological results.

Iterative polyketide synthesis via a consecutive carbonyl-protecting strategy

To address the difficulty in protecting a β-polycarbonyl compound, a method for the sequential protection of elongating carbonyl groups was demonstrated. The iterative chain elongation of a carboxylic acid with malonic acid half thioester followed by the protection of the resulting β-ketothioester was performed via the stepwise formation of an isoxazole ring using an O-protected oxime functionality. Yangonin and isosakuranetin were synthesized according to this procedure.

Synthesis and biological evaluation of novel flavanone derivatives as potential antipsychotic agents

In this study, a series of novel flavanone derivatives were designed and synthesized, and the antipsychotic activities of the target compounds were evaluated in vitro and in vivo. The results showed that synthesized compounds 7a–7g decreased the activity of dopamine D2 receptors in HEK293 cells co-transfected with D2 receptor/G protein α16a, with IC50 values of 0.051–0.35?μm. Compounds 7a–7g inhibited the over-production of nitric oxide stimulated by lipopolysaccharide/interferon-γ in BV-2 microglial cells. In mice, intragastric administration of 7d, 7e, and 7g reversed the increase in locomotor activity induced by MK-801 (an antagonist of NMDA receptors) and decreased the hyperactivity of climbing behavior induced by apomorphine (a dopamine receptor agonist). These results suggest that some of the novel flavanone derivatives have potential antipsychotic effects and may be useful in the treatment of schizophrenia.