29708-87-0

Usage

Uses

Used in Pharmaceutical Research:
Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, methyl ester, (1S,3R,4R,5R)is used as a research compound for exploring its potential bioactive properties. Its unique structure and stereochemistry may offer insights into the development of new pharmaceutical agents, particularly those targeting specific biological pathways or receptors.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, methyl ester, (1S,3R,4R,5R)- serves as a starting point for the synthesis of novel drug candidates. Its cyclohexanecarboxylic acid and dihydroxyphenyl groups can be further modified to create derivatives with enhanced pharmacological properties, such as improved potency, selectivity, or bioavailability.
Used in Drug Development:
Cyclohexanecarboxylic acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, methyl ester, (1S,3R,4R,5R)is used as a lead compound in drug development. Its potential bioactivity and unique structural features make it a valuable asset in the search for new therapeutic agents. Further research and testing will be necessary to determine its suitability for specific medical applications and to optimize its pharmacological profile.
Used in Chemical Synthesis:
Cyclohexanecarboxylic acid,
3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-,
methyl ester, (1S,3R,4R,5R)can also be used as an intermediate in the synthesis of other complex organic molecules. Its cyclohexanecarboxylic acid and dihydroxyphenyl groups provide a versatile platform for the attachment of various functional groups, enabling the creation of a wide range of chemical entities with diverse applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 67-56-1 methanol 
• 202650-88-2 3-caffeoylquinic acid 
• 186581-53-3 diazomethane 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 327-97-9 neochlorogenic acid 
• 82592-68-5 (E)-3,4-di-O-acetylcaffeoyl 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 

Downstream Products

• 144881-13-0 (1S,3R,4R,5R)-1,3,4-Triacetoxy-5-[(E)-3-(3,4-diacetoxy-phenyl)-acryloyloxy]-cyclohexanecarboxylic acid methyl ester 
• 103744-79-2 di-O-methylchlorogenic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and biological evaluation of caffeic acid derivatives as potent inhibitors of α-MSH-stimulated melanogenesis

We have disclosed our effort to develop caffeic acid derivatives as potent and non-toxic inhibitors of α-MSH-stimulated melanogenesis to treat pigmentation disorders and skin medication including a cosmetic skin-whitening agent. The SAR studies revealed t

Novel Chlorogenic Acid Derivatives and Composition for Treating Inflammatory Disease Comprising the Same

The present invention relates to a novel chlorogenic acid derivative compound having anti-inflammatory activities and an anti-inflammatory composition comprising the same as an active ingredient. The chlorogenic acid derivative compound of the present invention inhibits overproduction of nitrogen oxide (NO) induced by treating LPS in macrophage. The chlorogenic acid derivative compound of the present invention suppresses activation of NF-κB which is a signal transmission-mediated transcription factor significant in an oxidative stress and inflammation-promoting path. The chlorogenic acid derivative compound of the present invention can be developed as medicine for various inflammatory diseases by inhibiting overproduction of nitrogen oxide and activation of NF-κB.

Synthesis of 1-O-methylchlorogenic acid: Reassignment of structure for MCGA3 isolated from bamboo (Phyllostachys edulis) leaves

The first synthesis of 1-O-methylchlorogenic acid is described. The short and efficient synthesis of this compound provides laboratory-scale quantities of the material to investigate its biological properties. The synthesis involves C-1 alkylation of the

In vitro evaluation of caffeoyl and cinnamoyl derivatives as potential prolyl oligopeptidase inhibitors

A screening of the natural product chlorogenic acid, isolated from the Brazilian medicinal plant Hypericum brasiliense, caffeic acid, cinnamic acid, and p-methoxycinnamic acid, and derivatives of caffeoylquinic, caffeoyl, and cinnamoyl against the enzymes prolyl oligopeptidase and dipeptidyl peptidase IV was carried out. Caffeoylquinic, caffeoyl, and cinnamoyl derivatives were prepared using simple derivatization procedures and through coupling reactions with the amino acid proline. The dipeptidyl peptidase IV assay showed inhibitory activity of the tested compounds at a high concentration (500 μM) in the range of 81.5-7.2%. In contrast, the derivatives methyl ester and 1,7-acetonide obtained from chlorogenic acid, and caffeic acid and its methyl ester derivative showed selectivity and activity as prolyl oligopeptidase inhibitors, with IC50 values of 3 to 14 mM.

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

Essential structure of co-pigment for blue sepal-color development of hydrangea

Blue sepal-color of Hydrangea macrophylla might be due to a supramolecular metal-complex pigment consisting of delphinidin 3-glucoside (1), co-pigments (5-O-caffeoylquinic acid (2), and/or 5-O-p-coumaroylquinic acid (3)) and Al 3+ in an aqueous

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.