Isochlorogenic acid A Chemical Properties

Melting point:

>175°C (dec.)

Boiling point:

826.2±65.0 °C(Predicted)

Density 

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

storage temp. 

-20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Off-white to yellow/brown crystalline solid.

pka

3.54±0.50(Predicted)

color 

Off-White to Pale Yellow

Stability:

Hygroscopic

InChIKey

KRZBCHWVBQOTNZ-PSEXTPKNSA-N

SMILES

O([C@@H]1C[C@](O)(C(=O)O)C[C@@H](OC(=O)C=CC2C=CC(O)=C(O)C=2)[C@H]1O)C(=O)C=CC1C=CC(O)=C(O)C=1 |&1:1,3,9,23,r|

Safety Information

Safety Statements 

24/25

WGK Germany 

3

RTECS 

GU8403966

HS Code 

29189900

Isochlorogenic acid A Usage And Synthesis

Description

3,5-Dicaffeoylquinic acid (3,5-DCQA) is a natural phenolic compound that has been found in L. japonica, I. kaushue, and other plants. It has antioxidant, anti-inflammatory, and antiviral biological activities. 3,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay (IC₅₀ = 71.8 μM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe (fMLF) and cytochalasin B (IC₅₀ = 1.92 μM). It inhibits HIV-1 integrase 3''-end processing, strand transfer, and disintegration in a cell-free assay (IC₅₀s = 0.33, 0.34, and 0.66 μg/ml, respectively) and inhibits HIV-1-induced cytotoxicity in MT-2 cells (ED₅₀ = 1 μg/ml). In vivo, 3,5-DCQA (25 mg/kg) protects mice from acute lung injury induced by LPS and decreases neutrophil count in bronchoalveolar lavage fluid (BALF).

Chemical Properties

Off-white crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from honeysuckle, honeysuckle, eucommia, and chrysanthemum.

Uses

Isochlorogenic Acid A is a phenolic compound shown to provide protection against oxidative stress cells. DNA protective agent.

Definition

ChEBI: 3,5-di-O-caffeoyl quinic acid is a carboxylic ester that is the diester obtained by the condensation of the hydroxy groups at positions 3 and 5 of (-)-quinic acid with the carboxy group of trans-caffeic acid. Isolated from Brazilian propolis and Suaeda glauca, it exhibits hepatoprotective and cytotoxic activities. It has a role as a metabolite, a hepatoprotective agent and an antineoplastic agent. It is a cyclitol carboxylic acid and a carboxylic ester. It is functionally related to a (-)-quinic acid and a trans-caffeic acid.

in vivo

References

[1] LI-YAN PENG. Constituents from Lonicera japonica[J]. Fitoterapia, 2000, 71 6: Pages 713-715. DOI: 10.1016/s0367-326x(00)00212-4
[2] KRISS DAYANA PANTOJA PULIDO  José H I M  Ana Julia Colmenares Dulcey. New caffeic acid derivative from Tithonia diversifolia (Hemsl.) A. Gray butanolic extract and its antioxidant activity[J]. Food and Chemical Toxicology, 2017, 109: Pages 1079-1085. DOI: 10.1016/j.fct.2017.03.059
[3] W E ROBINSON. Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1996, 93 13: 6326-6331. DOI: 10.1073/pnas.93.13.6326

Isochlorogenic acid A(2450-53-5)Related Product Information

• EPA
• Cryptochlorogenic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• Stearic acid
• Diethyl succinosuccinate
• Dibutyryl adenosine cyclophosphate calcium
• Isochlorogenic acid C,Isochlorogenic acid C，4,5-Dicaffeoylquinic acid
• Isochlorogenic Acid B
• Taxifolin
• Isochlorogenic acid C
• (E,E)-3,5-Di-O-caffeoylquinic acid
• Citric acid
• Ascoric Acid
• Fluorescein isothiocyanate isomer I
• [1S-(1alpha,3beta,4beta,5alpha)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxoallyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
• CYCLOHEPTYL ISOTHIOCYANATE
• Ethoxycarbonyl Isothiocyanate