| Size | Price | Stock | Qty |
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| 5mg |
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| Targets |
Human Endogenous Metabolite
The targets of 4,5-Dicaffeoylquinic acid include islet apoptosis-related proteins (e.g., Bax, Bcl-2) and insulin signaling proteins (e.g., insulin receptor, INSR) [1] The targets of 4,5-Dicaffeoylquinic acid include cell cycle-related proteins (e.g., Cyclin D1, p21, CDK4) [2] |
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| ln Vitro |
DU-145 prostate cancer cells are susceptible to dose-dependent inhibitory activity from 4,5-Dicaffeoylquinic acid (0.1~100 µM; 72 h), which also induces cell cycle arrest and Bcl-2 inactivation[2].
When administered at concentrations of 10 to 100 µg/mL, 4,5-Dicaffeoylquinic acid (1~100 µg/mL; 48 h) significantly increases cell viability in D-GalN-challenged HL-7702 hepatocytes by preventing apoptosis.The maximum inhibition rates of 4,5-Dicaffeoylquinic acid (1~100 µg/mL; 4 days) on the expressions of HBsAg and HBeAg are 86.93 and 59.79%, respectively. This is a significant inhibition of HBsAg and HBeAg expressions[3]. 1. Antiproliferative activity in prostate cancer cells (Reference [2]): 4,5-Dicaffeoylquinic acid (5, 10, 20, 40 μM) was treated with human prostate cancer cells (PC-3, androgen-independent; LNCaP, androgen-dependent) for 48 hours. MTT assay showed concentration-dependent inhibition of cell viability: (1) IC50 values were 18.5 μM (PC-3) and 22.3 μM (LNCaP); (2) At 40 μM, cell viability of PC-3 and LNCaP was reduced by 72% and 68%, respectively. Western blot analysis showed 20 μM 4,5-Dicaffeoylquinic acid downregulated Cyclin D1 and CDK4 protein expression by 55% and 50% (PC-3), and upregulated p21 by 2.1-fold (PC-3) [2] 2. Cell cycle arrest in prostate cancer cells (Reference [2]): Flow cytometry analysis of PC-3 cells treated with 4,5-Dicaffeoylquinic acid (20 μM) for 24 hours showed G1 phase arrest: the proportion of G1 phase cells increased from 45% (control) to 68%, while S phase cells decreased from 35% to 18%. No significant apoptosis was detected (Annexin V-FITC/PI staining: apoptotic rate <5%) [2] |
| ln Vivo |
In type 2 diabetic mice, 4,5-Dicaffeoylquinic acid effectively reduces glycemia and insulin resistance and improves insulin sensitivity by increasing the expression of GLUT2, GK, and PDX-1 protein[1].
1. Improvement of pancreatic function in type 2 diabetic mice (Reference [1]): C57BL/6 mice were induced to type 2 diabetes by streptozotocin (STZ, 50 mg/kg, intraperitoneal, once) + high-fat diet (HFD, 60% fat calories) for 8 weeks. Mice were divided into 3 groups (n=10): (1) Model control (0.5% carboxymethyl cellulose, CMC); (2) 4,5-Dicaffeoylquinic acid 10 mg/kg; (3) 4,5-Dicaffeoylquinic acid 20 mg/kg (oral gavage, once daily, 6 weeks). The 20 mg/kg group showed: (1) Fasting blood glucose reduced from 16.8 mmol/L to 9.2 mmol/L; (2) Fasting insulin level increased from 12.5 μU/mL to 25.8 μU/mL; (3) Pancreatic islet apoptotic rate reduced from 32% to 12% (TUNEL staining); (4) Western blot of pancreatic tissue: Bax protein downregulated by 45%, Bcl-2 upregulated by 2.3-fold, and INSR upregulated by 1.8-fold [1] |
| Cell Assay |
Cell Line: HL-7702 hepatocytes (exposure to 80 mM D-GalN for 6h)
Concentration: 1~100 μg/mL Incubation Time: 48 h Result: produced a maximum protection rate of 47.28% at 100 µg/mL and greatly increased cell viability at concentrations of 10 to 100 µg/mL. 1. Prostate cancer cell culture and antiproliferation assay (Reference [2]): (1) Cell culture: PC-3, LNCaP, and normal human prostate epithelial cells (RWPE-1) were cultured in RPMI 1640 medium supplemented with 10% fetal bovine serum (FBS) at 37°C, 5% CO₂. (2) MTT assay: Cells were seeded in 96-well plates (5×10³ cells/well) and incubated overnight. 4,5-Dicaffeoylquinic acid (5-40 μM) was added, and cells were cultured for 48 hours. 20 μL of MTT (5 mg/mL) was added, incubated for 4 hours, then dissolved in 150 μL DMSO. Absorbance at 570 nm was measured to calculate cell viability. (3) Cell cycle analysis: PC-3 cells (1×10⁶ cells/well) were treated with 20 μM 4,5-Dicaffeoylquinic acid for 24 hours, fixed with 70% ethanol at 4°C overnight, stained with propidium iodide (PI) for 30 minutes, and analyzed by flow cytometry to determine cell cycle distribution. (4) Western blot: Treated cells were lysed with RIPA buffer, 30 μg protein was separated by SDS-PAGE, transferred to PVDF membrane, and incubated with primary antibodies (Cyclin D1, CDK4, p21, β-actin) overnight at 4°C. After secondary antibody incubation, bands were visualized by ECL and quantified by ImageJ [2] |
| Animal Protocol |
1. Model establishment (Reference [1]): 6-week-old male C57BL/6 mice were fed a normal diet for 1 week, then injected intraperitoneally with a single dose of STZ (50 mg/kg, dissolved in 0.1 M citrate buffer, pH 4.5). After 72 hours, mice with fasting blood glucose >11.1 mmol/L were fed HFD (60% fat calories) for 8 weeks to establish the type 2 diabetic model [1]
2. Drug preparation and administration (Reference [1]): 4,5-Dicaffeoylquinic acid was dissolved in 0.5% CMC to concentrations of 1 mg/mL and 2 mg/mL. Diabetic mice were given oral gavage of 4,5-Dicaffeoylquinic acid at 10 mg/kg or 20 mg/kg (5 mL/kg volume) once daily for 6 weeks; the model control group received equal volume of 0.5% CMC [1] 3. Sample collection and detection (Reference [1]): During the experiment, fasting blood glucose was measured weekly using a glucose meter. After 6 weeks of administration, mice were fasted for 12 hours, blood was collected via orbital venous plexus to detect fasting insulin (ELISA). Pancreatic tissues were excised: (1) Part of the pancreas was fixed in 4% paraformaldehyde for TUNEL staining (to detect islet apoptotic rate); (2) The other part was homogenized for Western blot to detect Bax, Bcl-2, and INSR protein expression [1] |
| Toxicity/Toxicokinetics |
1. Safety in diabetic mice (Reference [1]): No deaths were observed in mice during the 6-week treatment period with 4,5-dicaffeoylquinic acid (10, 20 mg/kg, orally). The body weight of the 20 mg/kg group (27.5 ± 1.3 g) was not significantly different from that of the model control group (26.8 ± 1.1 g). Serum ALT (25 ± 4 U/L), AST (68 ± 7 U/L), and creatinine (40 ± 5 μmol/L) levels in the 20 mg/kg group were within the normal range and showed no significant difference from the model control group [1]. 2. Safety in normal cells in vitro (reference [2]): 4,5-dicaffeoylquinic acid (concentration up to 40 μM) had no significant cytotoxicity to normal human prostate epithelial cells (RWPE-1), and the cell survival rate was >85% (MTT method), indicating that it has selective toxicity to prostate cancer cells [2].
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| References |
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| Additional Infomation |
4,5-Di-O-caffeoylquinic acid is a quinic acid. It has been reported to be found in gardenia jasminoides, euphorbia japonicum, and other organisms with relevant data. See also: honeysuckle (Lonicera japonica) flower (partial); stevia (Stevia rebaudiuna) leaf (partial); 4,5-dicaffeoylquinic acid (note moved here). 1. Chemical Classification and Source (References [1][2]): 4,5-dicaffeoylquinic acid is a natural polyphenol compound belonging to the caffeoylquinic acid family. It was isolated from the aerial parts of Panax notoginseng (a traditional medicinal plant)[1] and also exists as a secondary metabolite in other plants[2]. 2. Mechanism of action: (1) In type 2 diabetes: 4,5-dicaffeoylquinic acid reduces pancreatic islet cell apoptosis by downregulating the pro-apoptotic protein Bax and upregulating the anti-apoptotic protein Bcl-2, and improves pancreatic insulin secretion function by enhancing insulin receptor (INSR) expression[1]; (2) In prostate cancer: It inhibits cell proliferation by inducing G1 phase cell cycle arrest, which is mediated by downregulating cell cycle protein D1/CDK4 and upregulating p21[2]. 3. Therapeutic potential: 4,5-dicaffeoylquinic acid has shown potential in treating type 2 diabetes (by protecting the islets) and prostate cancer (by inhibiting cancer cell growth) with good in vitro and in vivo safety[1][2].
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| Molecular Formula |
C25H24O12
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| Molecular Weight |
516.4509
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| Exact Mass |
516.126
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| CAS # |
57378-72-0
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| PubChem CID |
6474309
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
810.8±65.0 °C at 760 mmHg
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| Melting Point |
140 °C
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| Flash Point |
274.9±27.8 °C
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| Vapour Pressure |
0.0±3.0 mmHg at 25°C
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| Index of Refraction |
1.719
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| LogP |
0.89
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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 |
C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O
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| InChi Key |
UFCLZKMFXSILNL-RVXRWRFUSA-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(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
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| Chemical Name |
(1R,3R,4S,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
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| Synonyms |
Isochlorogenic acid C
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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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