5746-55-4

Basic information

• Product Name: (1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid
• Synonyms: (1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid
• CAS NO: 5746-55-4
• Molecular Formula: C₁₆H₁₈O₈
• Molecular Weight: 338.31
• Mol File: 5746-55-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 613.2°Cat760mmHg
• Flash Point: 227°C
• Appearance: /
• Density: 1.55g/cm³
• Vapor Pressure: 6.8E-16mmHg at 25°C
• Refractive Index: 1.661
• PKA: 3.90±0.50(Predicted)
• CAS DataBase Reference: (1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid(5746-55-4)
• EPA Substance Registry System: (1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid(5746-55-4)

Safety Data

• Hazardous Substances Data: 5746-55-4(Hazardous Substances Data)

Usage

General Description

(1R,3S,4R,5S)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-cyclohexane-1-carboxylic acid is a complex chemical compound with a cyclohexane backbone. It contains three hydroxyl groups at the 1st, 3rd, and 4th positions, as well as an enoyl group attached to the 5th position of the cyclohexane ring. Additionally, it has a carboxylic acid functional group at the 1st position. The presence of the hydroxyl and enoyl groups makes it potentially useful as a natural antioxidant. It is important to handle and store this compound with caution, as it may pose health hazards if not managed properly.

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 
• 30802-00-7 p-coumaroyl-coenzyme A 
• 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 
• 209965-31-1 quinic acid bisacetonide 
• 108608-03-3 4-hydroxycinnamic acid chloride 
• 35949-53-2 (-)-4,5-cyclohexylidenequinic acid lactone 
• 108-94-1 cyclohexanone 
• 185900-09-8 C₁₉H₃₂O₆Si 

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.

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.

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.