67337-82-0

Basic information

• Product Name: (±)-hesperetin 7'-O-α-D-glucopyranoside
• CAS NO: 67337-82-0
• Molecular Weight: 464.426
• Mol File: 67337-82-0.mol

Chemical Properties

• CAS DataBase Reference: (±)-hesperetin 7'-O-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-hesperetin 7'-O-α-D-glucopyranoside(67337-82-0)
• EPA Substance Registry System: (±)-hesperetin 7'-O-α-D-glucopyranoside(67337-82-0)

Safety Data

• Hazardous Substances Data: 67337-82-0(Hazardous Substances Data)

Upstream product

• 520-26-3 hesperidin 
• 520-33-2 (S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone 

Downstream Products

• 67322-18-3 (S)-5-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-chroman-4-one 

Relevant articles and documents

GLUCOSYLATION OF EXOGENOUS FLAVANONES BY GRAPEFRUIT (CITRUS PARADISI) CELL CULTURES

Key Word Index - Citrus paradisi; Rutaceae; grapefruit; biotransformation; glucosylation; plant cell cultures; flavanones; flavanone glycosides; prunin; hesperitin 7-O-glucoside; 1H NMR.Grapefruit (Citrus paradisi) cells in suspension cultures did not accumulate flavanone glycosides but were able to specifically O-glucosylate exogenous naringenin and hesperitin at position 7.The products were extracted from the cultures using a new technique: absorption on an Amberlite XAD-2 resin and further purification by BioGel-P4 column chromatography.The flavanone glycosides obtained were analyzed by high-resolution 1H NMR and the spectra compared to authentic flavanone aglycones, mono- and diglycosides.

Optimization of regioselective α-glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase

The regioselective α-glucosylation of hesperetin was achieved by a transglycosylation reaction catalyzed by cyclodextrin glucanotransferase (CGTase) from Thermoanaerobacter sp. using soluble starch as glucosyl donor. By combining mass spectrometry (ESI-TOF) and 2D-NMR analysis, the main monoglucosylated derivative was fully characterized (hesperetin 7-O-α-D-glucopyranoside). In order to increase the yield of monoglucoside, several reaction parameters were optimized: Nature and percentage of cosolvent, composition of the aqueous phase, glucosyl donor, temperature, and the concentrations of hesperetin and soluble starch. Under the optimal conditions, which included the presence of 30% of bis(2-methoxyethyl) ether as cosolvent, the maximum concentration of monoglucoside was approximately 2 mM, obtained after 24 h of reaction. To our knowledge, this is the first report of direct glucosylation of hesperetin employing free enzymes instead of whole cells.