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3,5-Dicaffeoylquinic acid

Cat No.:V31246 Purity: ≥98%
Isochlorogenic acid A (3,5-Dicaffeoylquinic acid) is a natural phenolic acid with antimutagenic, anti-HBV (hepatitis B virus), anti-HIV (Human Immunodeficiency Virus), antioxidant, antibacterial and anti~inflammatory activities.
3,5-Dicaffeoylquinic acid
3,5-Dicaffeoylquinic acid Chemical Structure CAS No.: 2450-53-5
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Isochlorogenic acid A (3,5-Dicaffeoylquinic acid) is a natural phenolic acid with antimutagenic, anti-HBV (hepatitis B virus), anti-HIV (Human Immunodeficiency Virus), antioxidant, antibacterial and anti~inflammatory activities.
Biological Activity I Assay Protocols (From Reference)
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.
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].
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.
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.
References

[1]. 3,5-Dicaffeoylquinic acid isolated from Artemisia argyi and its ester derivatives exert anti-leucyl-tRNA synthetase of Giardia lamblia (GlLeuRS) and potential anti-giardial effects. Fitoterapia. 2012 Oct;83(7):1281-5.

[2]. Long-term cultured hairy roots of chicory-a rich source of hydroxycinnamates and 8-deoxylactucin glucoside. Appl Biochem Biotechnol. 2013 Dec;171(7):1589-601.

[3]. Isolation and identification of phenolic compounds from Gynura divaricata leaves. Pharmacogn Mag. 2011 Apr;7(26):101-8.

[4]. Isochlorogenic acid A promotes melanin synthesis in B16 cell through the β-catenin signal pathway. Acta Biochim Biophys Sin (Shanghai). 2017 Sep 1;49(9):800-807.

[5]. Reversal of Trimethyltin-Induced Learning and Memory Deficits by 3,5-Dicaffeoylquinic Acid. Oxid Med Cell Longev. 2016;2016:6981595.

[6]. Antioxidant and anti-inflammatory activities of 3,5-dicaffeoylquinic acid isolated from Ligularia fischeri leaves. Food Sci Biotechnol 24, 257–263 (2015).

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.
See also: 3,5-Di-O-caffeoylquinic acid (annotation moved to).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C25H24O12
Molecular Weight
516.4509
Exact Mass
516.126
CAS #
2450-53-5
PubChem CID
6474310
Appearance
White to light yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
826.2±65.0 °C at 760 mmHg
Melting Point
170-172ºC
Flash Point
280.4±27.8 °C
Vapour Pressure
0.0±3.2 mmHg at 25°C
Index of Refraction
1.719
LogP
1.05
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
9
Heavy Atom Count
37
Complexity
825
Defined Atom Stereocenter Count
2
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
InChi Key
KRZBCHWVBQOTNZ-RDJMKVHDSA-N
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
Chemical Name
(3R,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
HS Tariff Code
2934.99.9001
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?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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.

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