73263-62-4

Basic information

• Product Name: 1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-
• Synonyms: 1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-;5-O-caffeoylshikimic acid;(3R)-3β,4β-Dihydroxy-5α-[3-(3,4-dihydroxyphenyl)acryloyloxy]-1-cyclohexene-1-carboxylic acid;5-[(E)-caffeoyl]shikimic acid
• CAS NO: 73263-62-4
• Molecular Formula: C₁₆H₁₆O₈
• Molecular Weight: 336.29
• Mol File: 73263-62-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 635.1°C at 760 mmHg
• Flash Point: 236.5°C
• Appearance: /
• Density: 1.6g/cm³
• Vapor Pressure: 5.28E-17mmHg at 25°C
• Refractive Index: 1.689
• PKA: 4.27±0.70(Predicted)
• CAS DataBase Reference: 1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-(73263-62-4)
• EPA Substance Registry System: 1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-(73263-62-4)

Safety Data

• Hazardous Substances Data: 73263-62-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A carboxylic ester obtained by formal condensation of the carboxy group of (E)-caffeic acid with the 5-hydroxy group of shikimic acid.

InChI:InChI=1/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1

Upstream product

• 90927-40-5 3a,6,7,7a-tetrahydro-7-hydroxy-2,2-dimethyl-[3aR-(3aα,7α,7aα)]-1,3-benzodioxole-5-carboxylic acid 
• 40983-58-2 methyl shikimate 
• 138-59-0 shikimic acid 
• 98631-72-2 3,4-diacetoxycinnamoyl chloride 
• 88165-26-8 methyl 3,4-O-isopropylideneshikimate 

Downstream Products

• 83864-99-7 (E)-3-(2,2-diphenylbenzo[d][1,3]dioxolen-5-yl) acrylic acid 
• 331-39-5 caffeic acid 
• 138-59-0 shikimic 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.

Profiling and characterization by LC-MSn of the chlorogenic acids and hydroxycinnamoylshikimate esters in mate (Ilex paraguariensis)

The chlorogenic acids of mate (Ilex paraguariensis) have been investigated qualitatively by LC-MSn. Forty-two chlorogenic acids were detected and all characterized to regioisomeric level on the basis of their fragmentation pattern in tandem MS spectra, 24 of them for the first time from this source. Both chlorogenic acids based on trans-and cis-cinnamic acid substituents were identified. Assignment to the level of individual regioisomers was possible for eight caffeoylquinic acids (1-8), five dicaffeoylquinic acids (20-24), six feruloylquinic acids (9-14), two diferuloyl quinic acids (25 and 26), five p-coumaroylquinic acids (15-19), four caffeoyl-p-coumaroylquinic acids (34-37), seven caffeoyl-feruloylquinic acids (27-33), three caffeoyl-sinapoylquinic acids (38-40), one tricaffeoylquinic acid (41), and one dicaffeoyl-feruloylquinic acid (42). Furthermore, four caffeoylshikimates (43-46), three dicaffeoylshikimates (47-49), one tricaffeoylshikimate (51), and one feruloylshikimate (50) have been detected and shown to possess characteristic tandem MS spectra and were assigned by comparison to reference standards.