103215-48-1

Basic information

• Product Name: (-)-epicatechin 8-C-β-D-glucopyranoside
• CAS NO: 103215-48-1
• Molecular Weight: 452.415
• Mol File: 103215-48-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (-)-epicatechin 8-C-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-epicatechin 8-C-β-D-glucopyranoside(103215-48-1)
• EPA Substance Registry System: (-)-epicatechin 8-C-β-D-glucopyranoside(103215-48-1)

Safety Data

• Hazardous Substances Data: 103215-48-1(Hazardous Substances Data)

Upstream product

• 50-99-7 D-glucose 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 103215-61-8 8-C-β-D-glucopyranosyl(-)-epicatechin 4-β-benzylthioether 
• 2280-44-6 D-Glucose 

Downstream Products

• 103215-50-5 (2S,3R,4R,5S,6R)-2-[(2R,3R)-2-(3,4-Dimethoxy-phenyl)-3-hydroxy-5,7-dimethoxy-chroman-8-yl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 

Relevant articles and documents

Application of a molecular sensory science approach to alkalized cocoa (Theobroma cacao): Structure determination and sensory activity of nonenzymatically C-glycosylated flavan-3-ols

Application of comparative taste dilution analyses on nonalkalized and alkalized cocoa powder revealed the detection of a velvety, smoothly astringent tasting fraction, which was predominantly present in the alkalized sample. LC-MS/MS analysis, 1D- and 2D-NMR, and CD spectroscopy as well as model alkalization reactions led to the unequivocal identification of the velvety, smoothly astringent molecules as a series of catechin- and epicatechin-C- glycopyranosides. Besides the previously reported (-)-epicatechin-8-C-β-D- galactopyranoside, additional flavan-3-ol-C-glycosides, namely, (-)-epicatechin-8-C-β-D-glucopyranoside, (-)-catechin-8-C-β-D- glucopyranoside, (-)-catechin-6-C-β-D-glucopyranoside, (-)-epicatechin-6-C- β-D-glucopyranoside, (-)-catechin-8-C-β-D-galactopyranoside, (-)-catechin-6-C-β-D-galactopyranoside, (-)-catechin-6-C,8-C-β-D- diglucopyranoside, (-)-epicatechin-6-C,8-C-β-D-digalactopyranoside, (-)-catechin-6-C,8-C-β-D-digalactopyranoside, and epicatechin-6-C,8-C- β-D-diglucopyranoside, were identified for the first time in cocoa. Most surprisingly, these phenol glycoconjugates were demonstrated by model experiments to be formed via a novel nonenzymatic C-glycosylation of flavan-3-ols. Using the recently developed half-tongue test, human recognition thresholds for the astringent and mouth-drying oral sensation were determined to be between 1.1 and 99.5 μmol/L (water) depending on the sugar and the intramolecular binding position as well as the aglycone.

Tannins and related compounds. XXXVIII. Isolation and characterization of flavan-3-ol glucosides and procyanidin oligomers from cassia bark (Cinnamomum cassia Blume)

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