1093679-73-2

Basic information

• Product Name: Caffeic Acid 3-β-D-Glucuronide
• Synonyms: Caffeic Acid 3-β-D-Glucuronide;5-[(1E)-2-Carboxyethenyl]-2-hydroxyphenyl β-D-Glucopyranosiduronic Acid;Caffeic acid 3-O-b-D-glucuronide
• CAS NO: 1093679-73-2
• Molecular Formula: C₁₅H₁₆O₁₀
• Molecular Weight: 356.28154
• Product Categories: Aromatics;Glucuronides;Metabolites & Impurities;Aromatics, Glucuronides, Metabolites & Impurities
• Mol File: 1093679-73-2.mol

Chemical Properties

• Melting Point: >150°C (dec.)
• Appearance: /
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: Caffeic Acid 3-β-D-Glucuronide(CAS DataBase Reference)
• NIST Chemistry Reference: Caffeic Acid 3-β-D-Glucuronide(1093679-73-2)
• EPA Substance Registry System: Caffeic Acid 3-β-D-Glucuronide(1093679-73-2)

Safety Data

• Hazardous Substances Data: 1093679-73-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale Brown Solid

Upstream product

• 3843-74-1 methyl 3,4-dihydroxycinnamate 
• 92420-89-8 methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate 

Relevant articles and documents

First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption

A systematic investigation of the human metabolism of hydroxycinnamic acid conjugates was carried out. A set of 24 potential human metabolites of coffee polyphenols has been chemically prepared, and used as analytical standards for unequivocal identifications. These included glucuronide conjugates and sulfate esters of caffeic, ferulic, isoferulic, m-coumaric and p-coumaric acids as well as their dihydro derivatives. A particular focus has been made on caffeic and 3,4-dihydroxyphenylpropionic acid derivatives, especially the sulfate conjugates, for which regioselective preparation was particularly challenging, and have so far never been identified as human metabolites. Ten out of the 24 synthesized conjugates have been identified in human plasma and/or urine after coffee consumption. A number of these conjugates were synthesized, characterized and detected as hydroxycinnamic acid metabolites for the first time. This was the case of dihydroisoferulic acid 3′-O-glucuronide, caffeic acid 3′-sulfate, as well as the sulfate and glucuronide derivatives of 3,4-dihydroxyphenylpropionic acid.

Synthesis of hydroxycinnamic acid glucuronides and investigation of their affinity for human serum albumin

Hydroxycinnamic acids (HCAs) are among the most abundant dietary polyphenols. Recent bioavailability studies have shown that HCAs enter the blood circulation mainly as glucuronides, which are thus most likely to express their potential health effects. In