25514-46-9

Basic information

• Product Name: (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• Synonyms: (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid
• CAS NO: 25514-46-9
• Molecular Weight: 356.329
• Mol File: 25514-46-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid(25514-46-9)
• EPA Substance Registry System: (1S,3S,4R,5R)-3-((3-(3,4-dihydroxyphenyl)propanoyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic acid(25514-46-9)

Safety Data

• Hazardous Substances Data: 25514-46-9(Hazardous Substances Data)

Upstream product

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

Downstream Products

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

Relevant articles and documents

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

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.