| Identification | Back Directory | [Name]
Isochlorogenic acid A | [CAS]
2450-53-5 | [Synonyms]
3,5-CQA
CJ 4-16-4
Isochloric acid A
Isochlorogenic acid A
3,5-Dicaffeylquinic acid
3,5-Dicaffeoylquinic acid
ISOCHLOROGENIC ACID A(SH)
3',5'-Isochlorogenic acid A
Quinic acid 3,5-di-O-caffeate
Isochlorogenic acid A, froM Lonicera japonica
Isochlorogenic acid A，3,5-Dicaffeoylquinic acid
3,5-Di-O-caffeoylquinic acid，Isochlorogenic acid A
Isochlorogenic acid A, 98%, from Lonicera japonica
Isochlorogenic acid A, 98%, from Lonicera japonica Thunb.
1α,4α-Dihydroxy-3β,5α-bis[3-(3,4-dihydroxyphenyl)propenoyloxy]cyclohexanecarboxylic acid
1β,4β-Dihydroxy-3β,5α-bis[3-(3,4-dihydroxyphenyl)propenoyloxy]cyclohexanecarboxylic acid
1β,4β-Dihydroxy-3β,5α-bis[3-(3,4-dihydroxyphenyl)acryloyloxy]cyclohexane-1-carboxylic acid
3β,5α-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1β,4β-dihydroxycyclohexanecarboxylic acid
3α,5β-Bis[[1-oxo-3-(3,4-dihydroxyphenyl)-2-propenyl]oxy]-1α,4α-dihydroxycyclohexane-1-carboxylic acid
1β,4β-Dihydroxy-3β,5α-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1α-cyclohexanecarboxylic acid
(3R,5R)-3,5-Bis{[(2E)-3-(3,4-dihydroxyphenyl)-2-propenoyl]oxy}-1,4-dihydroxycyclohexanecarboxylic acid
Cyclohexanecarboxylic acid, 3,5-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,4-dihydroxy-, (1α,3R,4α,5R)- | [Molecular Formula]
C25H24O12 | [MDL Number]
MFCD00951290 | [MOL File]
2450-53-5.mol | [Molecular Weight]
516.46 |
| Chemical Properties | Back Directory | [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| |
| Hazard Information | Back Directory | [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.1,2 It has antioxidant, anti-inflammatory, and antiviral biological activities.2,3,4 3,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) 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).2,3 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).4 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).2 | [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]
Isochlorogenic acid A (5?and 10 mg/kg, p.o., once a day for 3 weeks) ameliorates cognitive impairment induced by TMT in ICR male mice[5].
| Animal Model: | TMT-induced ICR male mice[5] | | Dosage: | 5?and 10 mg/kg | | Administration: | p.o., once a day for 3 weeks | | Result: | Improved spatial memory and learning ability of mice in MWM test.
Reduced the TMT-induced increased AChE activity.
Reduced the MDA content compared to the TMT group. |
| [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 |
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