2957-21-3

Basic information

• Product Name: SAKURANETIN
• Synonyms: SAKURANETIN;5,4'-DIHYDROXY-7-O-METHOXYFLAVANONE;4',5-DIHYDROXY-7-METHOXYFLAVANONE;SAKURANETIN(SH);5,4''-DIHYDROXY-7-METHOXYFLAVANONE MONOHYDRATE WITH HPLC;SAKURANETIN hplc;5,4''-DIHYDROXY-7-METHOXYFLAVANONE;5,4''-DIHYDROXY-7-METHOXYFLAVANONE WITH HPLC
• CAS NO: 2957-21-3
• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28
• EINECS: 220-980-5
• Product Categories: Flavanones
• Mol File: 2957-21-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 153-154°C
• Boiling Point: 555.9 °C at 760 mmHg
• Flash Point: 212.4 °C
• Appearance: /
• Density: 1.37 g/cm³
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 7.42±0.40(Predicted)
• CAS DataBase Reference: SAKURANETIN(CAS DataBase Reference)
• NIST Chemistry Reference: SAKURANETIN(2957-21-3)
• EPA Substance Registry System: SAKURANETIN(2957-21-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 2957-21-3(Hazardous Substances Data)

Usage

Uses

Sakuranetin is a flavanone phytoalexin reported to play an important role in disease resistance in rice plants. Antifungal and antimicrobial activity.

Upstream product

• 529-39-5 5,4′-dihydroxy-7-methoxyflavanone 5-O-β-D-glucopyranoside 
• 77-78-1 dimethyl sulfate 
• 480-41-1 naringenin 
• 74-88-4 methyl iodide 
• 1195628-34-2 sakuranin 
• 31187-54-9 neosakuranin 
• 864969-45-9 (2S)-5-hydroxy-2-(1'-hydroxy-4'-oxocyclohexyl)-7-methoxychroman-4-one 
• 10236-47-2 naringin 
• 186581-53-3 diazomethane 

Downstream Products

• 3064-16-2 Acetic acid (S)-2-(4-acetoxy-phenyl)-7-methoxy-4-oxo-chroman-5-yl ester 
• 552-58-9 eriodictyol 
• 480-41-1 naringenin 
• 93012-86-3 7-methoxy-3',4',5-trihydroxyflavanone 
• 21785-09-1 7-methoxyflavanone 

Relevant articles and documents

Flavonoids and Naphthoquinones from Juglans nigra Bark

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Effect of naringenin and its derivatives on the probing behavior of myzus persicae (Sulz.)

Substances that alter insect behavior have attracted a lot of attention as potential crop protection agents. Naringenin (5,7,40-trihydroxyflavanone) is a naturally occurring bioactive flavanone. We evaluated the influence of naringenin on aphid activities during individual phases of probing and feeding and the effect of structural modifications of naringenin on its activity towards aphids. We monitored the probing behavior of Myzus persicae (Sulz.) (Hemiptera: Aphididae) using the Electrical Penetration Graph (EPG) technique. The chemical modifications were the substitution of hydrogen atoms with methyl, ethyl or pentyl groups and the replacement of the carbonyl group in naringenin and its derivatives with an oxime moiety. Depending on the substituents, the activity of naringenin-derived compounds varied in potency and mode of action. Naringenin was an attractant of moderate activity, which enhanced sap ingestion. The naringenin derivative with two methyl groups-7,40-di-O-methylnaringenin-was a deterrent, which hindered aphid probing in non-phloem tissues. Naringenin oxime derivatives with methyl substituents-7,40-di-O-methylnaringenin oxime, 7-O-methylnaringenin oxime, and 5,7,40-tri-O-methylnaringenin oxime-and the derivative with a pentyl substituent-7-O-pentylnaringenin oxime-were strong attractants which stimulated aphid probing in non-phloem tissues and the ingestion of phloem sap.

Cyclohexanoid protoflavanones from the stem-bark and roots of Ongokea gore

Phytochemical investigation of root and stem-bark of the West African medicinal plant Ongokea gore resulted in the isolation of four novel flavonoids with an unusual cyclohexyl substituent instead of the common aromatic ring B. The structures of the isolated compounds were elucidated by spectroscopic methods, mainly 1D and 2D NMR, and subsequently, the structures were corroborated by chemical conversion to (-)-(S)-sakuranetin. The absolute configurations, and preferred conformations were determined by NOE experiments and CD measurements.