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Product name: Isochlorogenic acid C
Synonym name: 4,5-Dicaffeoylquinic acid;Isochlorogenic acid C, Deleted Cas No.: 32451-88-0
Catalogue No.: BP0074
Cas No.: 57378-72-0
Formula: C25H24O12
Mol Weight: 516.455
Botanical Source:
Physical Description: White powder
Type of Compound: Phenylpropanoids
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20℃. Generally, these will be useable for up to two weeks.
The product could be supplied from milligrams to grams, up to kilograms
Inquire for bulk scale.
Descriptions:
Isochlorogenic acid C possesses potent hepatoprotective and anti-HBV effects; the anti-apoptotic and anti-injury effects could be achieved by its anti-oxidative properties and interfering the caspase-3 and TGF-beta expressions.;the anti-HBV target may mainly be at the downstream links of HBV replication process and is probably associated with blocking translation step.[1]
Isochlorogenic acid C has antioxidant activity.[2]
References:
[1] Hu S Q, Wu Y H, Hao B J, et al. J Med Plants Res, 2012,6(16):3199-206.
[2] Chang Y X, Liu J, Bai Y, et al.Plos One, 2014, 9(9):e106254-e106254.
[3] Xiao-Kun X U, Chen Z Y, Liao L P, et al. China Journal of Chinese Materia Medica, 2015, 40(6):1119-22.
HPLC of Isochlorogenic acid C
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
211.2800
1.1249
-1.0204
.8153
.7806
.2635
Low
88.9452
4.1411
No
No
No
No
Yes
No
0.0
Yes
Yes
Yes
Yes
Isochlorogenic acid C (CAS No.: 57378-72-0) is a naturally occurring quinic acid phenolic acid derivative widely distributed in various traditional Chinese medicinal materials and plants. As one of the isomers of chlorogenic acid, isochlorogenic acid C has attracted widespread attention in the field of natural product pharmacology in recent years due to its unique chemical structure and significant biological activity. Numerous studies have shown that isochlorogenic acid C has significant hepatoprotective effects and anti-hepatitis B virus (HBV) activity. Its anti-apoptotic and anti-cellular damage abilities are mainly attributed to its strong antioxidant properties and regulation of key molecular targets such as caspase-3 and transforming growth factor β1 (TGF-β1). In addition, the therapeutic potential of isochlorogenic acid C in cardiovascular diseases such as heart failure is gradually being revealed, with its targets covering multiple key proteins such as AMPK, EHMT2, APP, and PTPN1, demonstrating complex multi-target regulatory characteristics.
This paper aims to systematically review the chemical structure and physicochemical properties of isochlorogenic acid C, plant origin and extraction process, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, and to explore its potential prospects for clinical application, providing theoretical basis and research directions for subsequent drug development and clinical translation.
Isochlorogenic acid C is a quinic acid phenolic acid derivative and one of the isomers of chlorogenic acid, with the molecular formula C25H24O12 and a molecular weight of 516.4550. Its structural feature is that the quinic acid core is connected to multiple caffeic acid units by ester bonds, forming a triester structure. The LogP value of isochlorogenic acid C is 1.1249, indicating moderate lipid solubility, which facilitates cell membrane penetration. The polar surface area (TPSA) is 211.2800, reflecting its strong polarity and hydrogen bond donor/acceptor capacity, which aligns with its good water solubility (0.8153). This compound has low blood-brain barrier permeability, suggesting its limited distribution in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames mutagenicity test was 0.0, indicating that isochlorogenic acid C has no obvious mutagenicity and is relatively safe.
From the perspective of chemical stability, isochlorogenic acid C is relatively stable under neutral and weakly acidic conditions, but is prone to hydrolysis under strongly alkaline conditions. Its phenolic hydroxyl structure provides excellent antioxidant activity, which is an important basis for its biological activity.
Isochlorogenic acid C is widely found in various traditional Chinese medicinal materials and edible plants, with particularly high levels in Asteraceae plants, Rutaceae plants, and certain tea plants. For example, ginkgo leaves, chrysanthemums, green tea, and certain medicinal plants such as Scutellaria baicalensis and salvia miltiorrhiza have all been detected in isochlorogenic acid C. Its content is greatly affected by plant species, growing environment, harvest time, and processing methods.
Traditional methods for extracting isochlorogenic acid C mainly include water extraction, alcohol extraction, and their combined processes. Modern extraction technologies such as ultrasound-assisted extraction, microwave-assisted extraction, and supercritical fluid extraction are also applied to improve extraction efficiency and purity. The general process flow is: after drying and crushing the plants, extraction is performed with 70% ethanol or methanol, combined with ultrasonic-assisted extraction to promote the dissolution of active ingredients. After filtration and concentration, the extract was separated and purified using liquid chromatography (HPLC), ultimately obtaining high-purity isochlorogenic acid C.
During purification, reversed-phase high-performance liquid chromatography (RP-HPLC) is a commonly used separation method, combining mass spectrometry (MS) and nuclear magnetic resonance (NMR) technology to confirm the structure of isochlorogenic acid C. Optimizing the extraction process not only increases yield but also provides a solid material foundation for subsequent pharmacological research.
Research on the pharmacological activity of isochlorogenic acid C mainly focuses on liver protection, antiviral, antioxidant, and cardiovascular protection.
Numerous in vivo and in vitro experiments have shown that isochlorogenic acid C has a significant liver-protective effect. It eliminates free radicals, reduces oxidative stress, inhibits hepatocyte apoptosis, and protects the structural integrity of liver tissue. In animal models, isochlorogenic acid C can lower serum transaminase (ALT, AST) levels, alleviate liver fibrosis, and promote hepatocyte regeneration. Its anti-fibrotic effect is closely related to inhibiting the TGF-β1 signaling pathway, thereby blocking the activation of hepatic stellate cells and the excessive deposition of collagen.
Isochlorogenic acid C has a significant inhibitory effect on HBV. Cell experiments have shown that it can effectively reduce the expression of HBV surface antigen (HBsAg) and e antigen (HBeAg), inhibiting viral replication. Mechanistically, isochlorogenic acid C regulates intracellular redox states, inhibiting the expression and activity of virus-related proteins, thereby blocking a key step in the viral life cycle.
Isochlorogenic acid C is rich in phenolic hydroxyl group structures, demonstrating strong free radical scavenging ability. It can significantly reduce intracellular reactive oxygen species (ROS) levels, protect mitochondrial function, and decrease apoptosis caused by oxidative damage. The study found that isochlorogenic acid C blocks the apoptotic signaling pathway by downregulating Caspase-3 expression, thereby protecting cell survival.
In recent years, research on isochlorogenic acid C in cardiovascular diseases has increased, especially in heart failure models. It regulates energy metabolism and improves cardiomyocyte function by activating the AMPK signaling pathway. Additionally, isochlorogenic acid C can inhibit key targets such as EHMT2 and PTPN1, reduce myocardial inflammatory responses and fibrosis, and improve heart structure and function.
The multi-target mechanism of isochlorogenic acid C is the basis for its pharmacological activity. The main targets and signaling pathways involved are as follows:
As the enzyme executing apoptosis, Caspase-3 plays a central role in various liver injuries and myocardial cell apoptosis. Isochlorogenic acid C blocks the apoptotic cascade by inhibiting Caspase-3 activation, protecting cells from programmed death.
TGF-β1 is a key regulatory factor in fibrosis, promoting collagen deposition and fibrotic tissue formation. Isochlorogenic acid C inhibits the development of liver fibrosis and myocardial fibrosis by downregulating TGF-β1 expression.
AMPK serves as a central regulatory factor for cellular energy metabolism, regulating lipid metabolism, glucose metabolism, and cellular autophagy. Isochlorogenic acid C activates the AMPK signaling pathway, improving myocardial energy metabolism and enhancing myocardial cells' tolerance to ischemia and hypoxia.
EHMT2 participates in histone methylation regulating gene expression, affecting inflammatory responses and apoptosis. The inhibitory effect of isochlorogenic acid C on EHMT2 helps regulate the inflammatory status and survival of myocardial cells.
APP plays an important role in cardiovascular diseases and neurodegenerative disorders. Isorochlorogenic acid C regulates APP expression and may participate in the maintenance and protection of myocardial cell function.
In addition, isochlorogenic acid C also affects various proteins such as PTPN1, MAOA, ESR2, ABCB1, ALOX15, ABCG2, and FEN1, involving multiple biological processes including signal transduction, drug transport, and redox balance, demonstrating its multi-target and multi-pathway integrated regulatory characteristics.
The druggability parameters of isochlorogenic acid C indicate that it has good potential for drug development. The molecular weight of 516.4550 is moderate, and the LogP value of 1.1249 indicates moderate lipid solubility, which is beneficial for distribution in vivo. TPSA is relatively high, indicating strong polarity and good water solubility (0.8153), which is beneficial for oral absorption. The blood-brain barrier has low permeability, reducing the risk of central nervous system side effects.
Toxicological evaluation showed that isochlorogenic acid C did not inhibit hERG channels, indicating high cardiac safety. The Ames test was negative, indicating no risk of mutation. In addition, in vivo pharmacokinetic studies show that isochlorogenic acid C has moderate bioavailability after oral administration, with a suitable plasma half-life, mainly metabolized by the liver, and excreted primarily by the kidneys. Its metabolites are mostly hydroxylation and glucuronic acid conjugates, with good metabolic stability.
Based on these data, isochlorogenic acid C has good pharmacokinetics and safety characteristics, making it suitable for further drug development and clinical research.
As a natural quinic acid derivative, isochlorogenic acid C shows broad clinical application prospects due to its significant liver-protecting, anti-HBV, and cardiovascular protective effects. In the future, it holds potential value as an adjunct therapy for chronic liver diseases, viral hepatitis, and heart failure.
In the field of liver diseases, isochlorogenic acid C can be used as a new natural medicine for the prevention and treatment of liver fibrosis and hepatitis, especially suitable for combination with existing antiviral drugs to enhance efficacy and reduce side effects. In cardiovascular diseases, it regulates myocardial metabolism and inflammatory responses through multiple targets, making it a promising protector against heart failure and myocardial injury.
However, clinical research on isochlorogenic acid C is still in its early stages, urgently requiring systematic clinical trials to verify its safety and efficacy. At the same time, optimizing delivery routes and formulation development based on their pharmacokinetic characteristics will also be a key research focus for future research. Furthermore, in-depth analysis of its molecular mechanisms, especially the synergistic effects of multiple targets, will provide theoretical support for precision therapy.
In the future, by integrating modern medicinal chemistry, pharmacology, and clinical medicine, isochlorogenic acid C is expected to become an important candidate molecule in the development of natural product drugs, promoting the application and transformation of natural products in modern medicine.
As a natural quinic acid compound with rich biological activity, isochlorogenic acid C has become a hot topic in natural product pharmacology research due to its excellent liver-protective, antiviral, and cardiovascular protective effects. Its unique chemical structure endows it with excellent physicochemical properties and safety, while its broad pharmacological effects and multi-target mechanisms provide a solid foundation for its clinical application. Although further exploration is still needed in pharmacokinetics and clinical research, the potential of isochlorogenic acid C in natural drug development cannot be ignored. In the future, through systematic mechanistic research and clinical validation, isochlorogenic acid C is expected to become an important drug for treating liver and cardiovascular diseases, offering new treatment options for related patients.
Shenshuai
Wenjing
Hedandan
