4,5-Dicaffeoylquinic acid

Alias: Isochlorogenic acid C
Cat No.:V30082 Purity: ≥98%
4,5-Dicaffeoylquinic acid is a novel and potent hepatoprotective and anti-HBV effects.
4,5-Dicaffeoylquinic acid Chemical Structure CAS No.: 57378-72-0
Product category: HBV
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
4,5-Dicaffeoylquinic acid (Isochlorogenic acid C) is an antioxidant, can be isolated from Gynura divaricata and Laggera alata.In mice with type 2 diabetes, 4,5-Dicaffeoylquinic acid decreases islet cell apoptosis, enhances pancreatic function, and clearly inhibits yeast α-glucosidase. Via cell cycle arrest, 4,5-dicaffeoylquinic acid suppresses prostate cancer cells. The anti-apoptotic, anti-injury, and anti-hepatitis B virus properties of 4,5-dicaffeoylquinic acid are also present.
Biological Activity I Assay Protocols (From Reference)
Targets
Human Endogenous Metabolite
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].
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].
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.
References

[1]. Gynura divaricata rich in 3, 5-/4, 5-dicaffeoylquinic acid and chlorogenic acid reduces islet cell apoptosis and improves pancreatic function in type 2 diabetic mice. Nutr Metab (Lond). 2018 Oct 10;15:73.

[2]. Inhibition of Prostate Cancer Cells by 4,5-Dicaffeoylquinic Acid through Cell Cycle Arrest. Prostate Cancer. 2019 May 23;2019:4520645.

[3]. Evaluation of anti-apoptotic, anti-injury and antihepatitis B virus effects of isochlorogenic acid C in vitro. Journal of Medicinal Plants Research Vol. 6(16), pp. 3199-3206 30 April, 2012

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C25H24O12
Molecular Weight
516.4509
CAS #
57378-72-0
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
InChi Key
UFCLZKMFXSILNL-RVXRWRFUSA-N
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
Chemical Name
(1R,3R,4S,5R)-3,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
Synonyms
Isochlorogenic acid C
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~96.81 mM)
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.

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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.
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 corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
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.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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.

Biological Data
  • Histopathologic examination of pancreas in diabetic mice (HE stain, × 400). [1].Nutr Metab (Lond). 2018 Oct 10;15:73.
  • Insulin immunohistochemistry of pancreas in diabetic mice (× 400).[1].Nutr Metab (Lond). 2018 Oct 10;15:73.
  • Effect of GD on GLUT2, GK, MafA, PDX-1, Bcl-2, Bax, and caspase-3 protein expressions in pancreatic tissues. [1].Nutr Metab (Lond). 2018 Oct 10;15:73.
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