28757-27-9

Basic information

• Product Name: 5-[(β-D-Glucopyranosyl)oxy]-4',7-dihydroxyflavone
• Synonyms: 5-[(β-D-Glucopyranosyl)oxy]-4',7-dihydroxyflavone;Apigenin 5-glucoside;Apigenin 5-O-beta-D-glucopyraside;Apigenin 5-O-beta-D-glucopyranoside;Apigenin 5-O-glucoside;Apigenin 5-O-β-D-glucopyranoside
• CAS NO: 28757-27-9
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.38
• Mol File: 28757-27-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 226-227 °C
• Boiling Point: 814.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.642±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Methanol
• PKA: 6.44±0.40(Predicted)
• CAS DataBase Reference: 5-[(β-D-Glucopyranosyl)oxy]-4',7-dihydroxyflavone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[(β-D-Glucopyranosyl)oxy]-4',7-dihydroxyflavone(28757-27-9)
• EPA Substance Registry System: 5-[(β-D-Glucopyranosyl)oxy]-4',7-dihydroxyflavone(28757-27-9)

Safety Data

• Hazardous Substances Data: 28757-27-9(Hazardous Substances Data)

Usage

Uses

Apigenin 5-O-β-D-Glucopyranoside is an intermediate in synthesizing Apigenin 5-O-β-D-Glucuronide (A426510), a metabolite of Apigenin (A726500), Induces the reversion of transformed phenotypes of v-H-ras-transformed NIH 3T3 cells at low concentration (12.5 uM) by inhibiting MAP kinase activity. Also inhibits the proliferation of malignant tumor cells by G2/M arrest and induces morphological differentiation. Apigenin has also been reported to enhance the gap junction intracellular communication in liver cells.

Upstream product

• 133-89-1 UDP-glucose 
• 2196-14-7 7,4'-Dihydroxyflavon 

Downstream Products

• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 

Relevant articles and documents

Differentially evolved glucosyltransferases determine natural variation of rice flavone accumulation and UV-tolerance

Decoration of phytochemicals contributes to the majority of metabolic diversity in nature, whereas how this process alters the biological functions of their precursor molecules remains to be investigated. Flavones, an important yet overlooked subclass of flavonoids, are most commonly conjugated with sugar moieties by UDP-dependent glycosyltransferases (UGTs). Here, we report that the natural variation of rice flavones is mainly determined by OsUGT706D1 (flavone 7-O-glucosyltransferase) and OsUGT707A2 (flavone 5-O-glucosyltransferase). UV-B exposure and transgenic evaluation demonstrate that their allelic variation contributes to UV-B tolerance in nature. Biochemical characterization of over 40 flavonoid UGTs reveals their differential evolution in angiosperms. These combined data provide biochemical insight and genetic regulation into flavone biosynthesis and additionally suggest that adoption of the positive alleles of these genes into breeding programs will likely represent a potential strategy aimed at producing stress-tolerant plants.