87099-71-6

Basic information

• Product Name: Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)-
• Synonyms: 5-O-trans-p-coumaroylquinic acid;3-p-trans-coumaroylquinic acid;trans-3-O-p-coumaroylquinic acid;3-O-trans-Coumaroylquinic acid;5-O-(trans-p-coumaroyl)quinic acid
• CAS NO: 87099-71-6
• Molecular Formula: C16H18O8
• Molecular Weight: 338.314
• Mol File: 87099-71-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)-(87099-71-6)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)-(87099-71-6)

Safety Data

• Hazardous Substances Data: 87099-71-6(Hazardous Substances Data)

Usage

Description

Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)is a complex organic compound with a unique molecular structure. It is a cyclohexane derivative with three hydroxyl groups at positions 1, 3, and 4, and a 5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy] group. Cyclohexanecarboxylic acid,
1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-,
(1R,3R,4S,5R)exhibits chiral centers at positions 1, 3, 4, and 5, with the (1R,3R,4S,5R) configuration. Its chemical properties and potential applications make it an interesting compound for further research and development.

Uses

Used in Pharmaceutical Industry:
Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)can be used as a pharmaceutical compound for the development of new drugs. Its unique molecular structure and chiral centers may provide novel therapeutic properties and potential applications in treating various diseases.
Used in Food Industry:
As a butanol extract and a chemical constituent of Amygdalus persica L. flower, Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)can be used as a food additive or a natural flavoring agent. Its potential antioxidant properties may also contribute to the preservation and enhancement of food products.
Used in Cosmetic Industry:
Due to its antioxidant properties, Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)can be used in the cosmetic industry as an active ingredient in skincare products. It may help protect the skin from oxidative stress and promote overall skin health.
Used in Agricultural Industry:
Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-[[(2E)-3-(4-hydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (1R,3R,4S,5R)may also find applications in the agricultural industry as a natural pesticide or a growth promoter for crops. Its potential antioxidant properties could help protect plants from environmental stress and enhance their growth and productivity.

Upstream product

• 84184-55-4 methyl trans-3-(4-methoxymethoxyphenyl)propenoate 
• 213536-05-1 (2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate 
• 77-95-2 D-(-)-quinic acid 
• 61844-66-4 (E)-3-(4-(methoxymethoxy)phenyl)acrylic acid 
• 7400-08-0 p-Coumaric Acid 
• 3943-97-3 methyl 4-hydroxycinnamate 
• 108608-03-3 4-hydroxycinnamic acid chloride 
• 176798-26-8 (2S,3S,4aR,6S,8R,8aR)-6,8-Dihydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester 
• 185900-09-8 C₁₉H₃₂O₆Si 
• 108-94-1 cyclohexanone 
• 35949-53-2 (-)-4,5-cyclohexylidenequinic acid lactone 
• 209965-31-1 quinic acid bisacetonide 
• 27542-85-4 3-(4-acetoxyphenyl)acrylic acid 

Downstream Products

• 501-98-4 (Z)-p-coumaric acid 
• 7400-08-0 p-Coumaric Acid 

Relevant articles and documents

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (?)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-O-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure.

The biosynthesis of hydroxycinnamoyl quinate esters and their role in the storage of cocaine in Erythroxylum coca

Complexation of alkaloids is an important strategy plants utilize to facilitate storage in vacuoles and avoid autotoxicity. Previous studies have implicated hydroxycinnamoyl quinate esters in the complexation of purine alkaloids in Coffea arabica. The goal of this study was to determine if Erythroxylum coca uses similar complexation agents to store abundant tropane alkaloids, such as cocaine and cinnamoyl cocaine. Metabolite analysis of various E. coca organs established a close correlation between levels of coca alkaloids and those of two hydroxycinnamoyl esters of quinic acid, chlorogenic acid and 4-coumaroyl quinate. The BAHD acyltransferase catalyzing the final step in hydroxycinnamoyl quinate biosynthesis was isolated and characterized, and its gene expression found to correlate with tropane alkaloid accumulation. A physical interaction between chlorogenic acid and cocaine was observed and quantified in vitro using UV and NMR spectroscopic methods yielding similar values to those reported for a caffeine chlorogenate complex in C. arabica. These results suggest that storage of cocaine and other coca alkaloids in large quantities in E. coca involves hydroxycinnamoyl quinate esters as complexation partners.

Synthesis of designed acylquinic acid derivatives involved in blue color development of hydrangea and their co-pigmentation effect

The blue sepal color of hydrangea may be developed by an unstable stipramolecular metal-complex pigment composed of delphinidin 3-glucoside (1), 5-O-caffeoylquinic acid (2) and 5-O-p-coumaroylquinic acid (3) as co-pigments and Al3+ in aqueous s