57378-72-0

Basic information

• Product Name: (1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid
• Synonyms: (1R)-1,3β-Dihydroxy-4α,5α-bis[3-(3,4-dihydroxyphenyl)acryloyloxy]-1β-cyclohexanecarboxylic acid;(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid;1β,5α-Dihydroxy-3β,4β-bis[3-(3,4-dihydroxyphenyl)propenoyloxy]cyclohexanecarboxylic acid;3,4-O-Dicaffeoylquinic acid;4,5-Dicaffeoylquinic acid;Isochlorogenic acid C;Isochlorogenic acid C(4,5')
• CAS NO: 57378-72-0
• Molecular Formula: C₂₅H₂₄O₁₂
• Molecular Weight: 516.45
• Mol File: 57378-72-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 810.8 °C at 760 mmHg
• Flash Point: 274.9 °C
• Appearance: /
• Density: 1.64 g/cm³
• Vapor Pressure: 8.9E-28mmHg at 25°C
• Refractive Index: 1.719
• Storage Temp.: ?20°C
• PKA: 3.70±0.50(Predicted)
• CAS DataBase Reference: (1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid(57378-72-0)
• EPA Substance Registry System: (1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid(57378-72-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 57378-72-0(Hazardous Substances Data)

Usage

Description

(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid is a complex organic compound with a unique molecular structure. It is characterized by its multiple hydroxyl and carbonyl functional groups, which contribute to its potential biological activities and applications.

Uses

Used in Pharmaceutical Industry:
(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid is used as a pharmaceutical compound for its diverse biological activities. The presence of multiple hydroxyl groups allows for interactions with various biopolymers and macromolecules, making it a promising candidate for the development of new drugs and therapies.
Used in Antioxidant Applications:
(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid can be used as an antioxidant due to its ability to scavenge free radicals, such as DPPH radicals, and inhibit superoxide production in human neutrophils. Its antioxidant properties can be beneficial in preventing oxidative stress and related diseases.
Used in Anti-Inflammatory Applications:
(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid can be employed as an anti-inflammatory agent, as it has been shown to decrease prostaglandin E2 production in LPS-stimulated U937 cells and inhibit the synthesis of MCP3 in U937 cells.
Used in Anti-HIV Applications:
(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid has demonstrated anti-HIV activity by inhibiting HIV-1 integrase 3'' end processing, 3’ end joining, and disintegration. It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells, making it a potential candidate for the development of anti-HIV drugs.
Used in Anti-Melanogenic Applications:
(1R,3R,4S,5R)-1,5-Dihydroxy-3,4-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1-cyclohexanecarboxylic acid can be used to inhibit melanogenesis, as it has been shown to decrease the levels of proteins involved in melanin biosynthesis, such as tyrosinase, TRP-1, DCT, and MITF in B16F1 murine melanocytes. This property can be utilized in the development of skin-whitening agents and treatments for hyperpigmentation disorders.

InChI:InChI=1/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

Upstream product

• 327-97-9 neochlorogenic acid 
• 123716-83-6 1-O-(2,2,2-trichloroethoxycarbonyl)-1,5-γ-quinide 
• 98631-72-2 3,4-diacetoxycinnamoyl chloride 
• 13788-48-2 di-O-acetylcaffeic acid 
• 331-39-5 caffeic acid 
• 32384-42-2 (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 
• 485402-20-8 1-O-(2,2,2-trichloroethoxycarbonyl)-3,4-O-isopropyliden-1,5-γ-quinide 

Downstream Products

• 3843-74-1 methyl 3,4-dihydroxycinnamate 
• 89886-28-2 4-cis,5-cis-dicaffeoylquinic acid 
• 114637-83-1 (1S,3R,4R,5R)-3,4-bis{[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,5-dihydroxycyclohexane-1-carboxylic methyl ester 

Relevant articles and documents

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.