202650-88-2

Basic information

• Product Name: (-)-5-Caffeoyl quinic acid
• Synonyms: (1S)-1β,3β,4β-Trihydroxy-5α-[(E)-3-(3,4-dihydroxyphenyl)acryloyloxy]cyclohexane-1-carboxylic acid;(1S)-5α-[[(E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1β,3β,4β-trihydroxycyclohexanecarboxylic acid;(E)-3-(3,4-Dihydroxyphenyl)acrylic acid [(1R)-2α,3α,5-trihydroxy-5β-carboxycyclohexane-1β-yl] ester;1,4α,5α-Trihydroxy-3β-(3,4-dihydroxy-trans-cinnamoyloxy)cyclohexane-1β-carboxylic acid;1,4α,5α-Trihydroxy-3β-[(E)-3-(3,4-dihydroxyphenyl)propenoyloxy]cyclohexane-1β-carboxylic acid
• CAS NO: 202650-88-2
• Molecular Formula: C₁₆H₁₈O₉
• Molecular Weight: 354.30872
• Mol File: 202650-88-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 665.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.65±0.1 g/cm3(Predicted)
• PKA: 3.90±0.50(Predicted)
• CAS DataBase Reference: (-)-5-Caffeoyl quinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-5-Caffeoyl quinic acid(202650-88-2)
• EPA Substance Registry System: (-)-5-Caffeoyl quinic acid(202650-88-2)

Safety Data

• Hazardous Substances Data: 202650-88-2(Hazardous Substances Data)

Usage

General Description

(-)-5-Caffeoyl quinic acid, also known as 5-CQA, is a natural chemical compound found in various plants, including coffee beans and other fruits and vegetables. It is a type of hydroxycinnamic acid and belongs to the group of chlorogenic acids. 5-CQA is known for its antioxidant properties and has been studied for its potential health benefits, such as its anti-inflammatory and neuroprotective effects. It has also been linked to benefits for cardiovascular health and weight management. Additionally, 5-CQA may have potential applications in the food and pharmaceutical industries due to its various bioactive properties. Overall, 5-CQA is a promising compound that has garnered attention for its potential health and industrial applications.

Upstream product

• 327-97-9 neochlorogenic acid 
• 7400-08-0 p-Coumaric Acid 
• 77-95-2 D-(-)-quinic acid 
• 5783-35-7 (3aR)-5t-ethoxycarbonyloxy-7c-hydroxy-2,2-dimethyl-(3ar,7ac)-hexahydro-benzo[1,3]dioxole-5c-carboxylic acid methyl ester 
• 209965-31-1 quinic acid bisacetonide 
• 82592-68-5 (E)-3,4-di-O-acetylcaffeoyl chloride 
• 88623-81-8 3,4-diacetoxycinnamic acid 
• 364628-95-5 Trimethylsilyltetra-O-trimethylsilylchinat 
• 331-39-5 caffeic acid 
• 5800-10-2 (1S)-1-ethoxycarbonyloxy-3c-(3,4-dihydroxy-trans-cinnamoyloxy)-4t,5t-dihydroxy-cyclohexane-r-carboxylic acid methyl ester 

Downstream Products

• 55837-04-2 3-caffeoylchinasaeure permethyl 
• 29708-87-0 5-caffeoylquinic acid methyl ester 
• 1067649-99-3 1,7-pelargonaldehyde 3,4-pelargonaldehyde-chlorogenic acid diacetal 
• 1067649-98-2 1,7-pelargonaldehyde 3,4-pelargonaldehyde-chlorogenic acid diacetal 
• 1067650-01-4 1,7-pelargonaldehyde 3,4-pelargonaldehyde-chlorogenic acid diacetal 
• 1067650-00-3 1,7-pelargonaldehyde 3,4-pelargonaldehyde-chlorogenic acid diacetal 
• 1067649-92-6 1,7-(4-heptanone) 3,4-(4-heptanone)-chlorogenic acid diketal 
• 1067649-97-1 1,7-(9-heptadecanone) 3,4-(9-heptadecanone)-chlorogenic acid diketal 
• 1067649-93-7 1,7-(5-nonanone) 3,4-(5-nonanone)-chlorogenic acid diketal 
• 1067649-94-8 1,7-(6-undecanone) 3,4-(6-undecanone)-chlorogenic acid diketal 
• 1067649-95-9 1,7-(dihexyl ketone) 3,4-(dihexyl ketone)-chlorogenic acid diketal 
• 1067649-91-5 1,7-(3-pentanone) 3,4-(3-pentanone)-chlorogenic acid diketal 
• 877822-89-4 quinone of 5-caffeoylquinic acid 
• 331-39-5 caffeic acid 

Relevant articles and documents

Cloning and functional characterization of a p-coumaroyl quinate/shikimate 3′-hydroxylase from potato (Solanum tuberosum)

Chlorogenic acid (CGA) plays an important role in protecting plants against pathogens and promoting human health. Although CGA accumulates to high levels in potato tubers, the key enzyme p-coumaroyl quinate/shikimate 3′-hydroxylase (C3′H) for CGA biosynthesis has not been isolated and functionally characterized in potato. In this work, we cloned StC3′H from potato and showed that it catalyzed the formation of caffeoylshikimate and CGA (caffeoylquinate) from p-coumaroyl shikimate and p-coumaroyl quinate, respectively, but was inactive towards p-coumaric acid in in vitro enzyme assays. When the expression of StC3′H proteins was blocked through antisense (AS) inhibition under the control of a tuber-specific patatin promoter, moderate changes in tuber yield as well as phenolic metabolites in the core tuber tissue were observed for several AS lines. On the other hand, the AS and control potato lines exhibited similar responses to a bacterial pathogen Pectobacterium carotovorum. These results suggest that StC3′H is implicated in phenolic metabolism in potato. They also suggest that CGA accumulation in the core tissue of potato tubers is an intricately controlled process and that additional C3′H activity may also be involved in CGA biosynthesis in potato.

First efficient synthesis of chlorogenic acid

The first efficient synthesis of chlorogenic acid (1) was achieved in four steps (three purifications) from quinic acid (2). The overall yield was 65%, The key intermediate was quinic acid bisacetonide (6), selectively prepared by a modified kinetic aceta