14534-61-3

Basic information

• Product Name: (1S,3R,4R,5R)-3,4-Bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
• Synonyms: Isochlorogenic acid B, froM Lonicera japonica;3,4-Dicaffeoylquinic acid;Isochlorogenic acid B;(1S,3R,4R,5R)-3,4-Bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid;Isochlorogenic acid B，3,4-Dicaffeoylquinic acid;(1S)-1α,5α-Dihydroxy-3β,4α-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1β-cyclohexanecarboxylic acid;(1S)-4β,5α-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1β,3β-dihydroxycyclohexanecarboxylic acid;1β,3β-Dihydroxy-4β,5α-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1α-cyclohexanecarboxylic acid
• CAS NO: 14534-61-3
• Molecular Formula: C₂₅H₂₄O₁₂
• Molecular Weight: 516.45
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;The group of Chlorogenic acid
• Mol File: 14534-61-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 810.8 °C at 760 mmHg
• Flash Point: 274.9 °C
• Appearance: /
• Density: 1.64 g/cm³
• Vapor Pressure: 8.9E-28mmHg at 25°C
• Refractive Index: 1.719
• Storage Temp.: ?20°C
• Solubility: Methanol (Slightly)
• PKA: 3.70±0.50(Predicted)
• CAS DataBase Reference: (1S,3R,4R,5R)-3,4-Bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3R,4R,5R)-3,4-Bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid(14534-61-3)
• EPA Substance Registry System: (1S,3R,4R,5R)-3,4-Bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid(14534-61-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 14534-61-3(Hazardous Substances Data)

Usage

Uses

Isochlorgenic Acid is shown to provide antioxidant and DNA-protective activities.

InChI:InChI=1/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20?,23-,25-/m1/s1

Upstream product

• 327-97-9 neochlorogenic acid 
• 123716-83-6 1-O-(2,2,2-trichloroethoxycarbonyl)-1,5-γ-quinide 
• 98631-72-2 3,4-diacetoxycinnamoyl chloride 
• 13788-48-2 di-O-acetylcaffeic acid 
• 331-39-5 caffeic acid 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 485402-20-8 1-O-(2,2,2-trichloroethoxycarbonyl)-3,4-O-isopropyliden-1,5-γ-quinide 

Downstream Products

• 114637-83-1 (1S,3R,4R,5R)-3,4-bis{[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxycyclohexane-1-carboxylic methyl ester 
• 89886-28-2 4-cis,5-cis-dicaffeoylquinic acid 
• 3843-74-1 methyl 3,4-dihydroxycinnamate 

Relevant articles and documents

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.