4,5-Dicaffeoylquinic acid - 57378-72-0

4,5-Dicaffeoylquinic acid

Catalog Number: EVT-1477125
CAS Number: 57378-72-0
Molecular Formula: C25H24O12
Molecular Weight: 516.45
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
4,5-Dicaffeoylquinic acid (DCQA) is a naturally occurring polyphenolic compound found in various plants, including coffee, artichoke, and sweet potato. It belongs to the family of caffeoylquinic acids (CQAs), which are known for their antioxidant, anti-inflammatory, and neuroprotective properties. DCQA has gained significant attention in recent years due to its potential therapeutic applications in various diseases, including cancer, diabetes, and neurodegenerative disorders. This paper aims to provide a comprehensive review of the synthesis, chemical structure, biological activity, and potential applications of DCQA.
Applications in Various Fields
4,5-Dicaffeoylquinic acid has potential applications in various fields, including medical research, environmental research, and industrial research. In medical research, 4,5-Dicaffeoylquinic acid has been shown to have a role in drug development, as it exhibits potential therapeutic effects in various diseases. Clinical trials have shown that 4,5-Dicaffeoylquinic acid can improve glucose metabolism and reduce inflammation in patients with type 2 diabetes. Moreover, 4,5-Dicaffeoylquinic acid has been shown to exhibit anticancer activity by inducing apoptosis and inhibiting cell proliferation in various cancer cell lines. However, further studies are needed to determine the optimal dosage and safety of 4,5-Dicaffeoylquinic acid in humans. In environmental research, 4,5-Dicaffeoylquinic acid has been shown to have effects on ecosystems and can be used in pollution management. 4,5-Dicaffeoylquinic acid has been shown to exhibit phytotoxicity and can inhibit the growth of various plant species. Moreover, 4,5-Dicaffeoylquinic acid can be used as a natural herbicide to control weed growth. In industrial research, 4,5-Dicaffeoylquinic acid can be used in manufacturing processes to improve product quality and efficiency. 4,5-Dicaffeoylquinic acid has been shown to exhibit antimicrobial activity and can be used as a natural preservative in food and cosmetic products. However, health and safety considerations should be taken into account when using 4,5-Dicaffeoylquinic acid in industrial applications.

Properties

CAS Number

57378-72-0

Product Name

4,5-Dicaffeoylquinic acid

IUPAC Name

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

Molecular Formula

C25H24O12

Molecular Weight

516.45

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

SMILES

C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O

Synonyms

Isochlorogenic acid C
Method of Synthesis or Extraction
4,5-Dicaffeoylquinic acid can be synthesized by various methods, including chemical synthesis, enzymatic synthesis, and extraction from natural sources. Chemical synthesis involves the reaction of caffeic acid with quinic acid in the presence of a catalyst. Enzymatic synthesis involves the use of enzymes, such as peroxidase and tyrosinase, to catalyze the reaction between caffeic acid and quinic acid. Extraction from natural sources involves the isolation of 4,5-Dicaffeoylquinic acid from plants using various solvents, such as methanol, ethanol, and water. The efficiency and yield of each method vary depending on the source and the extraction conditions. However, extraction from natural sources is considered the most efficient and environmentally friendly method, as it does not involve the use of toxic chemicals.
Chemical Structure and Biological Activity
4,5-Dicaffeoylquinic acid has a molecular formula of C25H24O12 and a molecular weight of 516.45 g/mol. It consists of two caffeic acid moieties attached to a quinic acid backbone. The chemical structure of 4,5-Dicaffeoylquinic acid confers its antioxidant, anti-inflammatory, and neuroprotective properties. 4,5-Dicaffeoylquinic acid has been shown to inhibit the production of reactive oxygen species (ROS) and reduce oxidative stress in various cell types. It also exhibits anti-inflammatory activity by inhibiting the production of pro-inflammatory cytokines and enzymes. Moreover, 4,5-Dicaffeoylquinic acid has been shown to protect against neurodegeneration by modulating the expression of genes involved in neuronal survival and differentiation.
Biological Effects
4,5-Dicaffeoylquinic acid has been shown to exert various biological effects on cell function and signal transduction. It has been shown to modulate the activity of various signaling pathways, including the MAPK/ERK, PI3K/Akt, and NF-κB pathways. 4,5-Dicaffeoylquinic acid has also been shown to regulate the expression of genes involved in cell proliferation, apoptosis, and differentiation. Moreover, 4,5-Dicaffeoylquinic acid has been shown to exhibit potential therapeutic and toxic effects in various diseases, including cancer, diabetes, and neurodegenerative disorders.
Future Perspectives and Challenges
Despite the potential applications of 4,5-Dicaffeoylquinic acid, there are still limitations in its use and study. One of the main challenges is the lack of standardized methods for the extraction and quantification of 4,5-Dicaffeoylquinic acid from natural sources. Moreover, the optimal dosage and safety of 4,5-Dicaffeoylquinic acid in humans are still unknown, and further studies are needed to determine its pharmacokinetics and toxicity. Future trends and prospects in the application of 4,5-Dicaffeoylquinic acid in scientific research include the development of novel extraction methods, the identification of new biological targets, and the optimization of its therapeutic potential. Possible solutions and improvements include the use of advanced analytical techniques, such as mass spectrometry and nuclear magnetic resonance, to characterize the chemical structure of 4,5-Dicaffeoylquinic acid and its derivatives. Moreover, the use of nanotechnology and drug delivery systems can enhance the bioavailability and efficacy of 4,5-Dicaffeoylquinic acid in various diseases.
Conclusion:
In conclusion, 4,5-Dicaffeoylquinic acid is a naturally occurring polyphenolic compound with potential therapeutic applications in various diseases. 4,5-Dicaffeoylquinic acid can be synthesized by various methods, including chemical synthesis, enzymatic synthesis, and extraction from natural sources. 4,5-Dicaffeoylquinic acid has a unique chemical structure that confers its antioxidant, anti-inflammatory, and neuroprotective properties. 4,5-Dicaffeoylquinic acid has been shown to exert various biological effects on cell function and signal transduction and exhibits potential therapeutic and toxic effects in various diseases. 4,5-Dicaffeoylquinic acid has potential applications in various fields, including medical research, environmental research, and industrial research. However, further studies are needed to determine the optimal dosage and safety of 4,5-Dicaffeoylquinic acid in humans and to optimize its therapeutic potential.

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