105330-52-7

Upstream product

• 16198-01-9 (+)-pentaacetylcatechin 
• 942428-83-3 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 6858-46-4 uridine 5'-diphosphoglucose disodium salt 
• 154-23-4 catechin 
• 133-89-1 UDP-glucose 

Downstream Products

• 105330-61-8 (2S,3R,4S,5S,6R)-2-[4-((2R,3S)-3-Hydroxy-5,7-dimethoxy-chroman-2-yl)-2-methoxy-phenoxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

New flavanol O-glycosides in grape and wine

The presence of monomeric and dimeric flavan-3-ol monohexosides was investigated in grapes and wines. Polyphenol extracts were prepared from grape seeds and skins (Syrah, Merlot, and Cabernet-Sauvignon) sampled at three different developmental stages. Different wines (Tannat, Alicante, Syrah, Merlot, and Grenache) were also studied. The different samples obtained were analyzed by UPLC-ESI-IT-MS. Specific molecular ions corresponding to flavan-3-ol hexosides were detected by using targeted molecular ions with specific m/z values: 451 for (epi)catechin hexosides, and 739 for procyanidin dimer hexosides. 4′-O-β-glucosyl-(+)-catechin and 7-O-β-glucosyl-(+)-catechin were obtained by using a glucosyl transferase from apple, UGT71A15, and their structures determined by NMR. These glucosylated monomers and the dimers were identified in all analyzed grape seed and several skin extracts at the different stages and in wines made from different varieties.

Catechin Glucosides: Occurrence, synthesis, and stability

Catechins are flavonoids with suggested health benefits, but are unstable during storage, processing and, after ingestion, during gut transit. We hypothesized that catechin glucosidos, which occur in various plants, could be more stable than unsubstituted catechin, and additionally be deglucosylated in the gut and so act to deliver catechin in a form able to be absorbed. (+)-Catechin O-glucosides from various sources have been used in the course of this investigation. (+)-Catechin 3'-O-β-D-glucopyranoside (C3'G), (+)-catechin 5-O-β-D-glucopyranoside (C5G), and (+)-catechin 3-O-β-D-glucopyranoside (C3G) were chemically synthesized. (+)-Catechin 4'-O-β-D-glucopyranoside (C4'G) and (+)-catechin 7-O-β-D-glucopyranoside (C7G) were prepared enzymically using preparations from lentil and barley. In general, but with some exceptions, the (+)-catechin glucosidos were more stable between pH 4 and 8 than (+)-catechin, with C3'G exhibiting greatest stability. The intestinal metabolism of (+)-catechin and all (+)-catechin glucosides in the gut was determined by perfusion of rat intestine in vivo. C3'G and C5G were extensively deglycosylated in the gut, and C3'G showed greatest apparent "absorption" as calculated by the difference between effluent and influent. The results show the potential of catechin glucosides, especially C3'G, as more stable prescursors of catechin.