Isochlorogenic acid C Chemical Properties

Boiling point:

810.8±65.0 °C(Predicted)

Density 

1?+-.0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMF: 30 mg/ml; DMF:PBS (pH 7.2) (1:5): 0.16 mg/ml; DMSO: 5 mg/ml

form 

A solid

pka

3.70±0.50(Predicted)

color 

White to off-white

InChIKey

UFCLZKMFXSILNL-GCBRTHAASA-N

SMILES

[C@@]1(O)(C(O)=O)C[C@@H](O)[C@H](OC(=O)C=CC2=CC=C(O)C(O)=C2)[C@H](OC(=O)C=CC2=CC=C(O)C(O)=C2)C1

Safety Information

WGK Germany 

3

Isochlorogenic acid C Usage And Synthesis

Description

4,5-Dicaffeoylquinic acid (4,5-DCQA) is a polyphenol originally isolated from G. fagetorum and G. pseudomollugo that has diverse biological activities, including anti-HIV replication, antioxidative, anti-inflammatory, and anti-melanogenic properties. It inhibits HIV-1 integrase 3'' end processing, 3’ end joining, and disintegration with IC₅₀ values of 0.13, 0.24, and 0.3 μg/ml, respectively. It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an EC₅₀ value of 2 μg/ml. 4,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay (IC₅₀ = 19.8 μM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe (fMLF; ) and cytochalasin B (; IC₅₀ = 1.49 μM). It decreases prostaglandin E₂ (PGE₂; ) production in LPS-stimulated U937 cells when used at concentrations of 5 and 10 μg/ml but increases it when used at 200 μg/ml and increases production of TNF-α at concentrations ranging from 5 to 200 μg/ml. It inhibits the synthesis of MCP3 in U937 cells. 4,5-DCQA (25 μM) inhibits melanogenesis by 84% and decreases the levels of proteins involved in melanin biosynthesis, including tyrosinase, TRP-1, DCT, and MITF in B16F1 murine melanocytes.

Uses

4,5-Dicaffeoylquinic Acid is a selective inhibitor of human immunodeficiency virus type 1 integrase.

Definition

ChEBI: 4,5-di-O-caffeoylquinic acid is a quinic acid.

in vivo

References

[1] A. K. BOGAEVSKII  M. I B  L I Dranik. The hydroxycinnamic acids of Galium fagetorum and G. pseudomollugo[J]. Chemistry of Natural Compounds, 1970, 6 6: 761-762. DOI: 10.1007/bf00565353
[2] YU-LI CHEN. Ilex kaushue and Its Bioactive Component 3,5-Dicaffeoylquinic Acid Protected Mice from Lipopolysaccharide-Induced Acute Lung Injury[J]. Scientific Reports, 2016, 6 1. DOI: 10.1038/srep34243
[3] M. D. SANTOS. Effects of Caffeoylquinic Acid Derivatives and C-Flavonoid from Lychnophora ericoides on in vitro Inflammatory Mediator Production[J]. Natural Product Communications, 2010, 35 1. DOI: 10.1177/1934578x1000500512
[4] JI HOON HA  Soo N P. Mechanism underlying inhibitory effect of six dicaffeoylquinic acid isomers on melanogenesis and the computational molecular modeling studies[J]. Bioorganic & Medicinal Chemistry, 2018, 26 14: Pages 4201-4208. DOI: 10.1016/j.bmc.2018.07.014

Isochlorogenic acid C(57378-72-0)Related Product Information

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