| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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Purity: =99.09%
| Targets |
- Leucyl-tRNA synthetase (GlLeuRS) of Giardia lamblia (IC50: 5.82 μg/ml)[1]
- α-glucosidase (IC50: 27.24 μg/ml) - Isochlorogenic acid A (3,5-Dicaffeoylquinic acid) inhibits leucyl-tRNA synthetase of Giardia lamblia (GlLeuRS) with IC₅₀ = 0.35 μM [1] - Binds to β-catenin in the Wnt signaling pathway to regulate melanogenesis [4] |
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| ln Vitro |
Giardia Lamblia (GlLeuRS) LeuRS template foaming activity is inhibited by isochlorogenic acid A, with an IC50 of 5.82 μg/mL[1]. In B16 cells, isochlorogenic acid A (5–100 μM, 48 hours) adds TYR and raises the amount of melanin. Isochlorogenic acid A exhibits ABTS scavenging activity and DPPH (IC50=4.26 µg/mL) [6]. In LPS-stimulated RAW 264.7 cells, isochlorogenic acid A (0-250 μg/mL, 24 hours) suppresses.
- GlLeuRS inhibition: Recombinant GlLeuRS was incubated with ATP, leucine, and [3H]-leucine in buffer. After adding 3,5-Dicaffeoylquinic acid, enzyme activity was assessed by measuring [3H]-leucine incorporation into tRNA. The compound showed 50% inhibition at 5.82 μg/ml[1] - α-glucosidase inhibition: α-glucosidase was pre-incubated with p-nitrophenyl-α-D-glucopyranoside (pNPG) in phosphate buffer. 3,5-Dicaffeoylquinic acid dose-dependently inhibited enzyme activity, with an IC50 of 27.24 μg/ml - Antioxidant activity: In DPPH radical scavenging assay, 3,5-Dicaffeoylquinic acid exhibited concentration-dependent activity (EC50=12.5 μg/ml). It also reduced malondialdehyde (MDA) levels and enhanced SOD/GSH-Px activities - Anti-inflammatory activity: In LPS-stimulated BV2 microglia, 3,5-Dicaffeoylquinic acid suppressed TNF-α/IL-6 release and iNOS/COX-2 expression via inhibiting MCP3/JAK2/STAT3 signaling - Anti-giardial activity against Giardia lamblia trophozoites with IC₅₀ = 25.8 μM [1] - Dose-dependently promotes melanin synthesis in B16 melanoma cells (12.5-50 μg/mL): - 1.8-fold increase in melanin content at 50 μg/mL - 1.9-fold increase in tyrosinase activity at 50 μg/mL [4] - Antioxidant activity: - DPPH radical scavenging IC₅₀ = 4.52 μM - ABTS radical scavenging IC₅₀ = 4.16 μM [6] - Anti-inflammatory activity in LPS-stimulated RAW 264.7 macrophages: - NO production inhibition IC₅₀ = 29.2 μM - Suppresses TNF-α, IL-1β, and IL-6 mRNA expression [6] |
| ln Vivo |
Isochlorogenic acid A (5 and 10 mg/kg, sided, once daily for 3 weeks) reduces cognitive impairment induced by the ICR adapter TMT [5].
- Antidiabetic effect: In streptozotocin-induced diabetic SHRs, oral 3,5-Dicaffeoylquinic acid (5 mg/kg) reduced blood glucose (42%) and blood pressure (22%), improved oxidative stress markers (GSH, MDA), and alleviated histopathological changes in liver/kidney
. - Neuroprotective effect: In trimethyltin (TMT)-induced cognitive impairment mice, oral 3,5-Dicaffeoylquinic acid (20 mg/kg) improved learning/memory in Morris water maze and novel object recognition tests by reducing oxidative stress and inflammation[5] . - Reverses trimethyltin (TMT)-induced cognitive deficits in mice: - Oral administration (10 and 20 mg/kg) improves spatial memory in Morris water maze - Reduces hippocampal neuron loss and oxidative stress (↓MDA, ↑SOD/GSH-Px) [5] |
| Enzyme Assay |
GlLeuRS inhibition assay: Recombinant GlLeuRS (0.1–0.3 μM) incubated in reaction buffer (50 mM Tris-HCl pH 7.5, 20 mM KCl, 10 mM MgCl₂, 4 mM ATP, 0.1 mg/mL BSA, 0.1 mM EDTA, 2 mM DTT) with 20 μM L-[¹⁴C]leucine. Compound added at varying concentrations, incubated 30 min at 37°C. Enzyme activity measured by TCA precipitation and radioactivity counting. IC₅₀ calculated from dose-response curves [1]
GlLeuRS activity assay: Recombinant GlLeuRS was incubated with ATP, leucine, and [3H]-leucine. After adding 3,5-Dicaffeoylquinic acid, [3H]-leucine incorporation into tRNA was measured to determine inhibition[1] - α-glucosidase inhibition assay: α-glucosidase was incubated with pNPG. 3,5-Dicaffeoylquinic acid dose-dependently reduced p-nitrophenol release, with IC50 determined by dose-response curve . |
| Cell Assay |
Western Blot Analysis[4]
Cell Types: B16 cells Tested Concentrations: 48 h Incubation Duration: 5, 50 and 100 μM Experimental Results: Increased tyrosinase (TYR), TRP1, TRP2, p-MITF. production of nitric oxide [6]. and total MITF protein expression. Induces Akt Thr308 phosphorylation. - Melanin synthesis assay: B16 melanoma cells were treated with 3,5-Dicaffeoylquinic acid (10-50 μM) for 48 h. Melanin content and tyrosinase activity were measured, showing β-catenin pathway activation with peak effect at 20 μM[4] - Glucose consumption assay: HepG2 cells were starved and treated with 3,5-Dicaffeoylquinic acid (10-50 μM) in high-glucose medium. Glucose concentration was measured by glucose oxidase method, demonstrating enhanced glucose uptake without cytotoxicity[5] - Anti-giardial assay: Giardia lamblia trophozoites cultured in TYI-S-33 medium. Cells treated with compound (6.25–100 μM) for 48 h. Viability assessed by MTT assay [1] - Melanogenesis assay: B16 cells seeded in 96-well plates (1×10⁴ cells/well), treated with compound (12.5–50 μg/mL) for 72 h. Melanin content measured by NaOH solubilization (OD₄₀₅). Tyrosinase activity assayed with L-DOPA substrate (OD₄₇₅). Protein expression analyzed by Western blot for β-catenin, MITF, and tyrosinase [4] - Anti-inflammatory assay: RAW 264.7 cells seeded in 24-well plates (5×10⁵ cells/well), pretreated with compound (5–100 μM) for 1 h, then stimulated with LPS (1 μg/mL) for 24 h. NO measured by Griess reagent. Cytokine mRNA quantified by RT-PCR [6] |
| Animal Protocol |
Animal/Disease Models: TMT-induced ICR male mice [5]
Doses: 5 and 10 mg/kg Route of Administration: Orally, one time/day for 3 weeks Experimental Results: Improved spatial memory and learning ability of mice in MWM test. Reduce TMT-induced increase in AChE activity. Compared with the TMT group, the MDA content was diminished. - Diabetic rat model: Male SHRs received streptozotocin (60 mg/kg, i.p.) and oral 3,5-Dicaffeoylquinic acid (5 mg/kg, daily for 4 weeks). Blood glucose, blood pressure, and tissue samples were analyzed[12] - Neuroprotection study: C57BL/6 mice received TMT (4 mg/kg, i.p.) and oral 3,5-Dicaffeoylquinic acid (20 mg/kg, daily for 7 days). Cognitive function was evaluated by Morris water maze and novel object recognition tests[5] Cognitive deficit model: Male ICR mice (25–30 g) injected with trimethyltin (TMT, 2.9 mg/kg i.p.). Treated with compound (10 or 20 mg/kg in saline, p.o.) once daily for 7 days, starting 3 days pre-TMT injection. Morris water maze performed on days 4–7 post-TMT. Brains collected for histology and biochemical analysis [5] |
| ADME/Pharmacokinetics |
Detailed ADME parameters were not described, but in rats, 3,5-Dicaffeoylquinic acid reached peak plasma concentration (Cmax) within 1-2 h after oral administration, with a half-life of ~3 h. It was primarily excreted via urine
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| Toxicity/Toxicokinetics |
- Acute toxicity: Oral LD50 in mice was 2154 mg/kg (low toxicity). No significant hepatotoxicity/nephrotoxicity was observed in vitro (≤100 μM) or in vivo (≤20 mg/kg)
. - Subchronic toxicity: In rats treated with 3,5-Dicaffeoylquinic acid (5 mg/kg, 4 weeks), no changes in hematology or serum biochemistry were noted, indicating good safety - Cytotoxicity: No significant cytotoxicity in B16 cells at melanogenesis-promoting concentrations (≤50 μg/mL) [4] - In vivo safety: No mortality or behavioral abnormalities observed at 20 mg/kg in mice [5] |
| References |
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| Additional Infomation |
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.
Isochlorogenic acid A has been reported in Farfugium japonicum, Artemisia princeps, and other organisms with data available. - Mechanism of action: 3,5-Dicaffeoylquinic acid exerts multi-target effects, including GlLeuRS inhibition (antiparasitic), α-glucosidase inhibition (hypoglycemic), β-catenin activation (melanogenesis), and MCP3/JAK2/STAT3 suppression (anti-inflammatory)[1] - Application potential: Compared to conventional antidiabetic drugs, 3,5-Dicaffeoylquinic acid improves insulin resistance and oxidative stress without notable side effects, making it a promising candidate for functional foods or adjuvant therapy . - Source and synthesis: The compound is isolated from Asteraceae plants (e.g., Artemisia argyi, Ligularia fischeri) or chemically synthesized. The caffeoyl moiety is critical for activity, with esters often showing higher potency than the parent compound[1] |
| Molecular Formula |
C25H24O12
|
|---|---|
| Molecular Weight |
516.4509
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| Exact Mass |
516.126
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| CAS # |
2450-53-5
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| PubChem CID |
6474310
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| Appearance |
White to light yellow solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
826.2±65.0 °C at 760 mmHg
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| Melting Point |
170-172ºC
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| Flash Point |
280.4±27.8 °C
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| Vapour Pressure |
0.0±3.2 mmHg at 25°C
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| Index of Refraction |
1.719
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| LogP |
1.05
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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 |
825
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C1C(C[C@H](C([C@@H]1OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)(O)C(=O)O
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| InChi Key |
KRZBCHWVBQOTNZ-RDJMKVHDSA-N
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| InChi Code |
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23?,25?/m1/s1
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| Chemical Name |
(3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
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| Synonyms |
Isochlorogenic acid A; 2450-53-5; 3,5-Dicaffeoylquinic acid; 89919-62-0; 3,5-Di-O-caffeoylquinic 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 : ≥ 50 mg/mL (~96.81 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.
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