109717-92-2

Basic information

• Product Name: (Z)-1-(4-Hydroxy-3,5-dimethoxy-phenyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-(2,4,6-trihydroxy-phenyl)-propenone
• Synonyms: (Z)-1-(4-Hydroxy-3,5-dimethoxy-phenyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-(2,4,6-trihydroxy-phenyl)-propenone
• CAS NO: 109717-92-2
• Molecular Weight: 510.452
• Mol File: 109717-92-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-1-(4-Hydroxy-3,5-dimethoxy-phenyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-(2,4,6-trihydroxy-phenyl)-propenone(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-(4-Hydroxy-3,5-dimethoxy-phenyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-(2,4,6-trihydroxy-phenyl)-propenone(109717-92-2)
• EPA Substance Registry System: (Z)-1-(4-Hydroxy-3,5-dimethoxy-phenyl)-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-(2,4,6-trihydroxy-phenyl)-propenone(109717-92-2)

Safety Data

• Hazardous Substances Data: 109717-92-2(Hazardous Substances Data)

Upstream product

• 18470-06-9 malvidin 3-O-glucoside 

Relevant articles and documents

A comprehensive investigation of guaiacyl-pyranoanthocyanin synthesis by one-/two-dimensional NMR and UPLC-DAD-ESI-MSn

In red and rosé wines, the grape anthocyanins are progressively converted to more stable pigments, including phenylpyranoanthocyanins. One-/two-dimensional NMR and UPLC-DAD-ESI-MSn measurements were used to monitor the synthesis of guaiacylpyranomalvidin 3-O-glucoside from malvidin 3-O-glucoside and vinylguaiacol in model solutions and identify the products formed during the reaction. The highest conversion rates (30%, determined by 1H qNMR) were obtained with a small excess of vinylguaiacol in methanol/water (70/30) at pH 3 and 35 °C. Two reaction pathways competed with the formation of guaiacylpyranomalvidin 3-O-glucoside. The first one only concerns malvidin 3-O-glucoside and consists in C-ring cleavage with formation of malvone and smaller molecular weight breakdown products. This pathway is favored at higher pH and incubation temperature. At lower pH values or in the presence of large vinylguaiacol excess, faster consumption of malvidin 3-O-glucoside resulted from the formation of more complex pyranoanthocyanins substituted by vinylguaiacol oligomers.