62055-04-3

Basic information

• Product Name: 5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one
• Synonyms: 5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one
• CAS NO: 62055-04-3
• Molecular Weight: 584.534
• Mol File: 62055-04-3.mol

Chemical Properties

• CAS DataBase Reference: 5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one(62055-04-3)
• EPA Substance Registry System: 5-hydroxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-4H-1-benzopyran-4-one(62055-04-3)

Safety Data

• Hazardous Substances Data: 62055-04-3(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 31025-53-3 7-(β-D-glucopyranosyloxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 122472-95-1 5-acetoxy-2-phenyl-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-chromen-4-one 
• 31025-53-3 7-(β-D-glucopyranosyloxy)-5-hydroxy-2-phenyl-4H-1-benzopyran-4-one 

Relevant articles and documents

Acylated flavone glucosides: Synthesis, conformational investigation, and complexation properties

Acylated flavonoid glycosides are ubiquitous in plants; however, the possible influence of the acyl groups on the typical properties of flavonoids is rather poorly documented. In this work, a series of chrysin (= 5,7 dihydroxyflavone) glucosides acylated with aromatic and aliphatic acid residues has been synthesized in a simple three-step procedure. Aromatic acyl groups are shown to impose folded conformations on the chrysin glucosides owing to their ability to stack on the polyphenolic nucleus. The acyl groups may also cause significant changes in the ability of the flavonoid glucosides to bind hard metal ions and proteins, as demonstrated in this work in the case of Al3+ and bovine serum albumin.

Strategy for the vibrational circular dichroism study of a glycosylflavonoid evaluated as its peracetate. The case of bioactive 7-O-β-D-glucopyranosylchrysin

As it is difficult to study polyhydroxylated natural products by vibrational circular dichroism (VCD) due to their very limited solubility in infrared transparent solvents, 7-O-β-D-glucopyranosylchrysin (1), isolated from Mimosa rosei, was acetylated to provide 7-O-(2??,3??,4??,6??-tetraacetyl-β-D-glucopyranosyl)-5-acetylchrysin (2). Density functional theory (DFT) VCD spectra of 2 were calculated using the B3LYP, B3PW91, and PBEPBE functionals and the DGDZVP basis set to ascertain a good level of theory for calculating this kind of compounds. Statistical comparison of the experimental and calculated VCD spectra revealed that the frequently employed B3LYP and B3PW91 functionals provided good confidence levels with similar statistical results, allowing band assignments for the pyranoside portion of 2. This is the first report on a satisfactory statistical validation of a VCD measurement for such a glycopyranoside. In addition, in vitro cytotoxicity studies of 1 and 2 against the human colon cell line HT-29 and the human melanoma cell line UACC-62 by the MTT method were assayed. Moreover, the immunomodulatory response of 1 and 2 was evaluated by measuring TNF-α, IL-1β, and IL-10 levels by the ELISA technique. The results revealed low cytotoxicity of both compounds against cancer cells. However, flavonoid 1 upregulated the IL-1β production in lipopolysaccharide (LPS)-induced THP-1 macrophage, thus suggesting the potential of this molecule as an immunostimulant for cancer treatment.