3, 4-Dicaffeoylquinic acid

3, 4-Dicaffeoylquinic acid (3, 4-Di-O-caffeoylquinic acid), naturally isolated from Laggera alata, has antioxidative, DNA protective, neuroprotective and hepatoprotective properties. 3, 4-Dicaffeoylquinic acid exerts apoptosis-mediated cytotoxicity and α-glucosidase inhibitory effects. 3, 4-Dicaffeoylquinic acid possesses a unique mechanism of anti-influenza viral activity, that is, enhancing viral clearance by increasing TRAIL.

Product information

CAS Number: 14534-61-3

Molecular Weight: 516.45

Formula: C25H24O12

Synonym:

3,4-Di-O-caffeoylquinic acid

Isochlorogenic acid B

Chemical Name: (1S, 3R, 4R, 5R)-3, 4-bis({[(2E)-3-(3, 4-dihydroxyphenyl)prop-2-enoyl]oxy})-1, 5-dihydroxycyclohexane-1-carboxylic acid

Smiles: O[C@@H]1C[C@](O)(C[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)[C@@H]1OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(O)=O

InChiKey: UFCLZKMFXSILNL-PSEXTPKNSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Methanol : 83.33 mg/mL (161.35 mM; Need ultrasonic) DMSO : 50 mg/mL (96.81 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

3, 4-Dicaffeoylquinic acid acts as a greater primary antioxidant than its methanol extract, by having higher ferric reducing activity (EC50 2.18 μg/ml), β-carotene bleaching activity (EC50 23.85 μg/ml) and DPPH scavenging activity (EC50 68.91 μg/ml). 3, 4-Dicaffeoylquinic acid exhibits a remarkable dose-dependent inhibitory effect on NCI-H23 (human lung adenocarcinoma) cell lines (EC50 3.26 μg/ml) and is found to be apoptotic in nature based on a clear indication of DNA fragmentation. 3, 4-Dicaffeoylquinic acid also displays a concentration-dependent α-glucosidase inhibition with EC50 241.80 μg/ml.

References:

1. Takemura T, et al. 3,4-Dicaffeoylquinic Acid, a Major Constituent of Brazilian Propolis, Increases TRAIL Expression and Extends the Lifetimes of Mice Infected with the Influenza A Virus. Evid Based Complement Alternat Med. 2012;2012:946867.
2. Liu X, et al. Protective effect of isochlorogenic acid B on liver fibrosis in non-alcoholic steatohepatitis of mice. Basic Clin Pharmacol Toxicol. 2019;124(2):144-153.
3. Ooi KL, et al. Cytotoxic, apoptotic and anti-α-glucosidase activities of 3,4-di-O-caffeoyl quinic acid, an antioxidant isolated from the polyphenolic-rich extract of Elephantopus mollis Kunth. J Ethnopharmacol. 2011;135(3):685-695.

Products are for research use only. Not for human use.