5746-55-4

Usage

Uses

Used in Pharmaceutical Industry:
(1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid is used as a natural antioxidant for its potential to protect against oxidative stress and related health issues. Its presence of hydroxyl and enoyl groups may contribute to its antioxidant properties, making it a candidate for development in pharmaceutical formulations aimed at combating diseases associated with oxidative damage.
Used in Food Industry:
In the food industry, (1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid is used as a preservative to extend the shelf life of food products by preventing oxidation, which can lead to spoilage and degradation of quality.
Used in Cosmetic Industry:
(1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid is used as an ingredient in cosmetic products for its antioxidant properties, which can help protect the skin from environmental stressors and promote overall skin health.
It is important to handle and store (1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid with caution due to its potential health hazards if not managed properly, highlighting the need for safe practices in its application across various industries.

InChI:InChI=1/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16-/m0/s1

Upstream product

• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 204254-79-5 ethyl (3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-benzo[1,3]dioxole-5-carboxylate 
• 7400-08-0 para-coumaric acid 
• 27542-85-4 3-(4-acetoxyphenyl)acrylic acid 
• 77-95-2 D-(-)-quinic acid 
• 191916-39-9 methyl (-)-quinate 
• 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 
• 108608-03-3 4-hydroxycinnamic acid chloride 
• 30802-00-7 p-coumaroyl-coenzyme A 

Downstream Products

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

Relevant academic research and scientific papers

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.

CHLOROGENIC ACID DERIVATIVES AND THEIR USE AS ANTI-FUNGAL AGENTS

The invention provides chlorogenic acid derivatives of Formula (I) that are capable of inhibiting the growth of fungal cells and are useful as anti-fungal agents. The invention further provides the methods of inhibiting the growth of fungal cells and methods of treating a fungal infection in an animal by administering to the animal an effective amount of a compound of Formula I, either alone or in combination with another anti-fungal agent.

Synthesis of chlorogenic acid derivatives with promising antifungal activity

Derivatives of chlorogenic acid or its analogues were synthesized by coupling protected chlorogenic acid or its analogues with p-octyloxyaniline and selected amino acids. Most of the compounds exhibited significant potency against Cryptococcus neoformans and Candida species with low toxicity to brine shrimps. The 4,5-dihydroxyl groups in the quinic acid moiety were necessary for the activity and introduction of a free amino group increased the inhibitory activity against Aspergillus fumigatus.

Chlorogenic acid and synthetic chlorogenic acid derivatives: Novel inhibitors of hepatic glucose-6-phosphate translocase

The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (Gl-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose 6- phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. Gl-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.