| Size | Price | Stock | Qty |
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| 5mg |
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| Targets |
1,3-Dicaffeoylquinic acid targets multiple molecular pathways. It activates both phosphoinositide 3-kinase (PI3K) and extracellular regulated protein kinase 1/2 (Erk1/2) by stimulating their upstream tyrosine kinase A (Trk A). It also targets reactive oxygen species (ROS), Akt, and PI3K. The compound's neuroprotective effects are mediated through activation of these signaling pathways, while its anti-HIV activity involves inhibition of HIV-1 integrase.
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| ln Vitro |
In neurons, it has been demonstrated that 1,3-Dicaffeoylquinic Acid increases neuronal cell viability against Aβ(42) toxicity in a concentration-dependent manner. While stimulating its upstream tyrosine kinase A (Trk A), 1,3-dicaffeoylquinic acid activates extracellular regulated protein kinase 1/2 (Erk1/2) and phosphoinositide 3-kinase (PI3K)/Akt. The augmentation of inactivating phosphorylation of glycogen synthase kinase 3β (GSK3β) and the control of the expression of apoptosis-related protein Bcl-2/Bax are linked to the anti-apoptotic potential of 1,3-dicaffeoylquinic acid [2]. In OGD/reperfusion injury, 1,3-dicaffeoylquinic acid (10 μM, 20 μM, 50 μM, and 100 μM) can prevent GSH consumption and greatly increase cell viability prior to OGD/reperfusion. In OGD/reperfusion-treated astrocytes, 1,3-dicaffeoylquinic acid causes Nrf2 nuclear translocation and raises GCL activity; however, this effect is lost in Nrf2 siRNA-transfected cells [3].
In vitro, 1,3-Dicaffeoylquinic acid exhibits significant antioxidant activity and free radical scavenging effects. It increases neuronal cell viability against Aβ(42) toxicity in a concentration-dependent manner. The compound shows potent inhibition of HIV-1 integrase, with activity comparable to 1,5-DCQA. It also activates PI3K and Erk1/2 signaling pathways through Trk A stimulation. These activities suggest broad therapeutic potential in neurodegenerative diseases and viral infections. |
| ln Vivo |
In Wistar rats, 1-O-ABL and 1,3-dicaffeoylquinic acid (32.0 mg/kg, orally) are absorbed very quickly. 1-O-ABL and 1,3-dicaffeoylquinic acid have maximal plasma concentrations of 19.1 ± 6.9 ng/mL and 44.5 ± 7.1 ng/mL, respectively [1].
In vivo, 1,3-Dicaffeoylquinic acid (Cynarin) has demonstrated neuroprotective effects. The compound exhibits choleretic properties and promotes bile flow. Its anti-hyperlipidemic activity has been observed in animal models. The compound shows potential as an immunosuppressive agent. These in vivo activities support its traditional use in herbal medicine and suggest potential therapeutic applications in metabolic and inflammatory disorders. |
| Enzyme Assay |
General protocols for cell-free enzyme assays involve incubating purified HIV-1 integrase with a DNA substrate and varying concentrations of 1,3-Dicaffeoylquinic acid in reaction buffer containing 20 mM HEPES pH 7.5, 10 mM MnCl2, and 10 mM DTT at 37°C for 30-60 minutes. The reaction is stopped by adding EDTA, and products are analyzed by gel electrophoresis or fluorescence-based methods. IC50 values are determined from dose-response curves. Positive controls (known integrase inhibitors) and negative controls (vehicle only) are included.
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| Cell Assay |
General protocols for cell-based neuroprotection assays use primary neurons or neuronal cell lines (e.g., SH-SY5Y) cultured in neurobasal medium. Cells are seeded in 96-well plates and pretreated with various concentrations of 1,3-Dicaffeoylquinic acid for 2-4 hours, then exposed to Aβ(42) oligomers for 24-48 hours. Cell viability is measured using MTT, LDH release, or calcein-AM staining. Apoptosis is assessed by caspase-3/7 activity or TUNEL staining. The protective effect is calculated as the percentage increase in cell viability compared to Aβ-treated controls.
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| Animal Protocol |
General protocols for in vivo neuroprotection studies use transgenic mouse models of Alzheimer's disease (e.g., APP/PS1 mice) or acute Aβ injection models. 1,3-Dicaffeoylquinic acid is administered orally or intraperitoneally at doses ranging from 10-100 mg/kg daily for 2-4 weeks. Cognitive function is assessed using Morris water maze, Y-maze, or novel object recognition tests. Brain tissues are collected for biochemical analysis of Aβ levels, oxidative stress markers, and inflammatory cytokines. Histological examination evaluates plaque burden and neuronal loss.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 1,3-Dicaffeoylquinic acid indicate that it is a natural product with moderate oral bioavailability. As a caffeoylquinic acid derivative, it undergoes extensive metabolism in the gastrointestinal tract and liver. The compound is rapidly absorbed and distributed to various tissues, including the brain, which supports its neuroprotective effects. Elimination occurs primarily through biliary excretion and renal clearance. Detailed pharmacokinetic parameters such as half-life, Cmax, and AUC are compound- and formulation-dependent.
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| Toxicity/Toxicokinetics |
Toxicological data for 1,3-Dicaffeoylquinic acid suggest it has a favorable safety profile as a natural product. It is generally recognized as safe based on its presence in commonly consumed foods and traditional herbal preparations. No significant acute toxicity has been reported at therapeutic doses. However, comprehensive toxicological studies, including chronic toxicity, carcinogenicity, and reproductive toxicity assessments, are limited. As with any bioactive compound, high doses may cause adverse effects, and caution is advised in sensitive populations.
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| References |
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| Additional Infomation |
1,3-dicaffeoylquinic acid has been reported to be found in chamomile, Indian aster, and other organisms with available data.
1,3-Dicaffeoylquinic acid (Cynarin) is a natural product with a long history of use in traditional medicine. It has been investigated for multiple therapeutic applications, including Alzheimer's disease (neuroprotection), HIV infection (integrase inhibition), hyperlipidemia, and immunosuppression. The compound activates PI3K/Akt and Erk1/2 signaling pathways. Despite promising preclinical data, it has not received regulatory approval as a pharmaceutical drug. Clinical trials are limited, and further research is needed to establish its efficacy and safety in humans. |
| Molecular Formula |
C25H24O12
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|---|---|
| Molecular Weight |
516.4509
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| Exact Mass |
516.126
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| CAS # |
19870-46-3
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| Related CAS # |
Cynarin;30964-13-7
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| PubChem CID |
6474640
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| Appearance |
White to yellow solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
819.9±65.0 °C at 760 mmHg
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| Flash Point |
278.1±27.8 °C
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| Vapour Pressure |
0.0±3.1 mmHg at 25°C
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| Index of Refraction |
1.719
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| LogP |
1.64
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| Hydrogen Bond Donor Count |
7
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
9
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| Heavy Atom Count |
37
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| Complexity |
887
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| Defined Atom Stereocenter Count |
4
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| SMILES |
O(C(/C(/[H])=C(\[H])/C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])=O)[C@@]1(C(=O)O[H])C([H])([H])[C@]([H])([C@]([H])([C@@]([H])(C1([H])[H])OC(/C(/[H])=C(\[H])/C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])=O)O[H])O[H]
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| InChi Key |
YDDUMTOHNYZQPO-PSEXTPKNSA-N
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| InChi Code |
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
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| Chemical Name |
(1S,3R,4R,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~193.63 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.84 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.84 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (4.84 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9363 mL | 9.6815 mL | 19.3630 mL | |
| 5 mM | 0.3873 mL | 1.9363 mL | 3.8726 mL | |
| 10 mM | 0.1936 mL | 0.9681 mL | 1.9363 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT02621060 | COMPLETEDWITH RESULTS | Drug: Placebo Drug: Chlorogenic acid |
Impaired Glucose Tolerance | University of Guadalajara | 2015-09 | Phase 2 |
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