25514-46-9

Upstream product

• 327-97-9 chlorogenic acid 
• 35949-53-2 (-)-4,5-cyclohexylidenequinic acid lactone 
• 1078-61-1 dihydrocaffeic acid 
• 77-95-2 D-(-)-quinic acid 
• 202650-88-2 3-caffeoylquinic acid 
• 185900-09-8 C₁₉H₃₂O₆Si 
• 185900-11-2 3-(3,4-Dihydroxy-phenyl)-1-imidazol-1-yl-propan-1-one 
• 185900-12-3 C₂₈H₄₂O₁₀Si 

Downstream Products

• 1078-61-1 dihydrocaffeic acid 
• 77-95-2 1,3,4,5-tetrahydroxy-cyclohexanecarboxylic acid 
• 77-95-2 D-(-)-quinic acid 

Relevant academic research and scientific papers

Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis

We have disclosed our effort to develop caffeic acid derivatives as potent and non-toxic inhibitors of α-MSH-stimulated melanogenesis to treat pigmentation disorders and skin medication including a cosmetic skin-whitening agent. The SAR studies revealed t

Novel Chlorogenic Acid Derivatives and Composition for Treating Inflammatory Disease Comprising the Same

The present invention relates to a novel chlorogenic acid derivative compound having anti-inflammatory activities and an anti-inflammatory composition comprising the same as an active ingredient. The chlorogenic acid derivative compound of the present invention inhibits overproduction of nitrogen oxide (NO) induced by treating LPS in macrophage. The chlorogenic acid derivative compound of the present invention suppresses activation of NF-κB which is a signal transmission-mediated transcription factor significant in an oxidative stress and inflammation-promoting path. The chlorogenic acid derivative compound of the present invention can be developed as medicine for various inflammatory diseases by inhibiting overproduction of nitrogen oxide and activation of NF-κB.

Structure-activity relationship of caffeoylquinic acids on the accelerating activity on ATP production

Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β1-42-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure-activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.

Chlorogenic acid and synthetic chlorogenic acid derivatives: Novel inhibitors of hepatic glucose-6-phosphate translocase

The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (Gl-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose 6- phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. Gl-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.