86632-03-3

Usage

Uses

Used in Pharmaceutical Industry:
(1alpha,3R,4alpha,5R)-3,4,5-Tris[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1-hydroxycyclohexanecarboxylic acid is used as a potential therapeutic agent for various medical conditions due to its complex structure and the presence of multiple functional groups. The dihydroxyphenyl and propenoyl moieties, along with the carboxylic acid group, may contribute to its pharmacological properties, making it a candidate for drug development and research.
Used in Chemical Research:
In the field of chemical research, (1alpha,3R,4alpha,5R)-3,4,5-Tris[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1-hydroxycyclohexanecarboxylic acid serves as a subject for studying the synthesis of complex organic molecules and their potential applications. Its unique structure allows researchers to explore its reactivity, stability, and interactions with other molecules, which can lead to the discovery of new chemical reactions or the improvement of existing ones.
Used in Material Science:
(1alpha,3R,4alpha,5R)-3,4,5-Tris[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1-hydroxycyclohexanecarboxylic acid may also find applications in material science, particularly in the development of new polymers or composite materials. The presence of hydroxyl and carboxylic acid groups can enable the formation of hydrogen bonds and other interactions, which can influence the material's properties such as strength, flexibility, and stability.

InChI:InChI=1/C34H30O15/c35-21-7-1-18(13-24(21)38)4-10-29(41)47-27-16-34(46,33(44)45)17-28(48-30(42)11-5-19-2-8-22(36)25(39)14-19)32(27)49-31(43)12-6-20-3-9-23(37)26(40)15-20/h1-15,27-28,32,35-40,46H,16-17H2,(H,44,45)/b10-4+,11-5+,12-6+/t27-,28-,32?,34?/m1/s1

Upstream product

• 77-95-2 D-(-)-quinic acid 
• 98631-72-2 3,4-diacetoxycinnamoyl chloride 
• 191916-39-9 methyl (-)-quinate 
• 13788-48-2 di-O-acetylcaffeic acid 
• 331-39-5 caffeic acid 
• 485402-20-8 1-O-(2,2,2-trichloroethoxycarbonyl)-3,4-O-isopropyliden-1,5-γ-quinide 
• 18959-40-5 3,4-O-dimethoxycarbonyl caffeic acid 
• 16180-95-3 3,4-O-dimethoxycarbonyl caffeic acid chloride 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 

Relevant academic research and scientific papers

METHOD FOR MANUFACTURING 3,4,5-TRICAFFEOYLQUINIC ACID

Provided are a method for manufacturing 3,4,5-tricaffeoylquinic acid, which can produce 3,4,5-tricaffeoylquinic acid with high efficiency by a simple operation in a short process using inexpensive raw materials, and intermediate compounds. The method for manufacturing 3,4,5-tricaffeoylquinic acid of the invention includes at least Step (1) of allowing a compound represented by Formula (1) or a compound represented by Formula (2) to react with a compound represented by Formula (4); and Step (2) of deprotecting the product obtained in Step (1), and producing 3,4,5-tricaffeoylquinic acid:

METHOD FOR PRODUCING 3,4,5-TRICAFFEOYLQUINIC ACID

PROBLEM TO BE SOLVED: To provide a method for producing 3,4,5-tricaffeoylquinic acid capable of efficiently producing 3,4,5-tricaffeoylquinic acid in a short process by a simple operation. SOLUTION: Provided is a method for producing 3,4,5-tricaffeoylquin

Characterization and quantification of hydroxycinnamate derivatives in Stevia rebaudiana leaves by LC-MSn

Stevia rebaudiana leaves are used as a zero-calorie natural sweetener in a variety of food products in Asian countries, especially in Japan. In this study, the hydroxycinnamate derivatives of S. rebaudiana have been investigated qualitatively and quantita

Structure-activity relationship of caffeoylquinic acids on the accelerating activity on ATP production

Caffeoylquinic acid (CQA) is one of the phenylpropanoids which have various bioactivities such as antioxidant, antibacterial, anticancer, antihistamic, and other biological effects. We previously reported that 3,5-di-O-caffeoylquinic acid inhibited amyloid β1-42-induced cellular toxicity on human neuroblastoma SH-SY5Y cells and increased the mRNA expression level of glycolytic enzymes and the intracellular ATP level. To investigate structure-activity relationship on the accelerating activity on ATP production, we synthesized 1,4,5-tri-O-caffeoylquinic acid, 4,5-di-O-caffeoylquinic acid, 3,4,5-tri-O-caffeoylquinic acid, and other derivatives. Additionally, we evaluated intracellular ATP level in SH-SY5Y treated with each CQA derivative. As a result, 3,4,5-tri-O-caffeoylquinic acid showed the highest accelerating activity on ATP production among tested compounds. It was suggested that caffeoyl groups bound to quinic acid are important for activity and the more caffeoyl groups are bound to quinic acid, the higher accelerating activity on ATP production exhibits.