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Product name: Eugenin
Synonym name:
Catalogue No.: BP4075
Cas No.: 480-34-2
Formula: C11H10O4
Mol Weight: 206.197
Botanical Source: 5-Hydroxy-7-methoxy-2-methylchromone
Physical Description:
Type of Compound: Flavonoids
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
Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
HPLC of Eugenin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
59.6700
1.8200
1.8069
.3342
4.6811
36.8540
Low
86.1461
2.2406
Yes
No
Yes
No
Yes
Yes
1.2
No
No
Yes
No
Eugenin (CAS No.: 480-34-2) is a naturally occurring chromogen compound, originally isolated from Formosan Peucedanum japonicum, a plant endemic to Taiwan. As a natural product with multiple biological activities, chlorinochromein demonstrates significant pharmacological potential in anti-platelet aggregation, anti-tumor, and anti-inflammatory fields. In recent years, with in-depth research into the molecular mechanisms of major diseases such as cardiovascular diseases, neurodegenerative diseases, thrombotic diseases, and tumors, chlorinochrome ketone has attracted widespread attention due to its multi-target properties. This paper will systematically review the chemical structure and physicochemical properties of Chlorinochromeone, plant origin and extraction methods, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects, aiming to provide theoretical basis and research directions for its subsequent drug development and clinical translation.
Chloride ketone belongs to the chromogen class of compounds with the molecular formula C11H10O4 and a molecular weight of 206.1970. Structurally, cynochrome ketone contains a typical flavonoid backbone with hydroxyl and methoxy substituents, giving it certain polarity and biological activity. Its LogP value is 1.82, indicating moderate hydrophobicity, which facilitates membrane penetration without excessive hydrophobicity and affecting solubility. The topological pole surface area (TPSA) was 59.67 Ų, indicating good potential for cell absorption. The water solubility is 0.3342, which is moderately low in water solubility, which may affect its oral bioavailability. The blood-brain barrier penetration ability is relatively low, suggesting that its efficacy in the central nervous system may be limited. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames test value was 1.2, indicating a low genotoxicity risk and a certain safety basis.
Chlorogenic ketone was first isolated from Formosan Peucedanum japonicum, a plant belonging to the Apiaceae family, widely distributed in Taiwan and East Asia. Traditionally, Formosan Peucedanum japonicum has been used in folk herbal medicine for its anti-inflammatory and blood circulation-promoting effects. As one of its main active ingredients, chlorinochromein ketone has been purified and identified in recent years through modern separation technology.
Common methods for extracting chloranogen ketone include solvent extraction and column chromatography separation. Ethanol or methanol is usually used as extraction solvents, combined with ultrasound-assisted extraction to improve extraction efficiency. After vacuum concentration, the extract is purified using silica gel column chromatography or high-performance liquid chromatography (HPLC). During purification, the identification of cynochromein ketone mainly relies on technologies such as nuclear magnetic resonance (NMR), mass spectrometry (MS), and UV-Vis spectroscopy to confirm its structure and purity. In recent years, with the development of chromatography technology, ultra-high performance liquid chromatography (UPLC) and mass spectrometry (LC-MS/MS) have been widely used for qualitative and quantitative analysis of cylindrine chloride.
One of the most notable pharmacological activities of chlorochromein is its anti-platelet aggregation effect. Platelet aggregation is a key stage in thrombosis formation, and excessive activation can lead to cardiovascular and cerebrovascular events. In vitro experiments have shown that chlorogenic chlorinone can significantly inhibit platelet aggregation triggered by various inducers (such as ADP and collagen), reduce the expression of platelet activation markers, and lower the risk of thrombosis. Its antiplatelet action provides a potential natural drug candidate for the prevention and treatment of cardiovascular diseases.
Chlorochromeone exhibits cytotoxic effects on various tumor cell lines. Research shows that it can induce tumor cell apoptosis and inhibit cell proliferation and migration. Mechanistically, genushegenone exerts anti-tumor effects by regulating the expression of BCL2 family proteins, activating apoptosis-related signaling pathways. Additionally, chlorogenic ketone regulates tumor-related signaling pathways such as STAT3 and MAPK1, further enhancing its anticancer activity.
Eugenin also shows good activity in the field of anti-inflammation. It can inhibit the expression of inflammatory factors such as IL-6 and TNF-α, block activation of the NF-κB signaling pathway, and reduce inflammatory responses. By inhibiting the activity of the PTGS1/PTGS2 (COX-1/COX-2) enzyme, eugenin reduces prostaglandin synthesis and alleviates inflammatory symptoms. Additionally, its regulation of inflammation-related ion channels such as TRPV1 and TRPA1 suggests its potential application value in pain and inflammation-related diseases.
Although the blood-brain barrier penetration ability of clove genin is relatively low, its role in neurodegenerative disease models is gradually gaining attention. Eugenin can regulate neuroprotective targets such as BCL2, APP, and BACE1, reducing neuronal apoptosis and amyloid accumulation, and has potential neuroprotective effects. It activates the NFE2L2 (Nrf2) antioxidant pathway, enhancing cellular antioxidant capacity, and may have adjunctive therapeutic value for neurodegenerative diseases such as Parkinson's and Alzheimer's.
Eugenonone exerts antithrombotic effects by regulating thrombosis targeting targets related to thrombosis, such as SERPINE1, F3, F2, F10, TBXA2R, etc.). Its inhibition of blood coagulation factor activity, reducing the risk of thrombosis, combined with its anti-platelet aggregation properties, provides a multi-target intervention strategy for the prevention and treatment of thrombotic diseases.
The multiple pharmacological activities of eugenonone are attributed to its regulation of various key molecular targets. The main related targets and their mechanisms of action are as follows:
AMPK (PRKAA1): As a regulatory enzyme for cellular energy metabolism, AMPK activation helps improve cardiovascular function and inhibit tumor cell metabolism. Eugenone may play a protective role by activating the AMPK pathway, regulating cellular metabolic homeostasis.
BCL2: An anti-apoptotic protein that regulates cell survival and death. Eugenone induces tumor cell apoptosis by regulating BCL2 expression, promoting programmed cell death.
BACE1: β-secreted enzyme, involved in the production of β-amyloid protein in Alzheimer's disease. Chloranochlorone inhibits BACE1, helping to slow down neurodegenerative changes.
TLR4: Inflammatory signal receptor mediates immune response. Chlorochromein reduces inflammatory responses by inhibiting TLR4-mediated inflammatory signaling.
PTGS1/PTGS2 (COX-1/COX-2): catalyzes prostaglandin synthesis and is involved in inflammation and platelet function. Eugenochromone inhibits its activity, exerting anti-inflammatory and antiplatelet effects.
STAT3: Transcription factor, regulates cell proliferation and immune response. Eugenone inhibits STAT3 signaling, which helps with anti-tumor and anti-inflammatory effects.
NFE2L2 (Nrf2): a key factor regulating antioxidant responses. Chlorochromein activates the Nrf2 pathway, enhancing cellular antioxidant capacity and reducing oxidative stress damage.
Thrombosis-related targets (SERPINE1, F3, F2, F10, TBXA2R, etc.): Eugenonone inhibits thrombogenesis and improves hemorheological performance through multi-target synergistic action.
In addition, genusin ketone also affects various signaling molecules such as PRKCA, AKR1B1, ESR2, APEX1, ADORA3, PPARG, PIK3CA, LGALS3, and EGFR, indicating its broad bioregulatory capacity.
The druggability parameters of eugenonone indicate that it has certain potential for drug development. Moderate molecular weight and moderate LogP values benefit its bioavailability. The TPSA value is moderate, indicating good cell membrane penetration, but its blood-brain barrier penetration ability is relatively low, limiting its direct application in central nervous system diseases.
Low water solubility may affect oral absorption and requires formulation optimization or structural modification. hERG channels have no inhibitory effects, reducing the risk of cardiotoxicity. Ames trial results showed that it carries a low genotoxicity risk and is relatively safe.
Currently, pharmacokinetic research on chlorogenic ketone is still incomplete, and its absorption, distribution, metabolism, and excretion (ADME) characteristics in vivo require further systematic evaluation. Preliminary data suggest that its metabolism in vivo may involve enzymatic transformation in the liver, and the activity and toxicity of these metabolites require further research.
As a multi-target, multifunctional natural product, canicolorone shows promising application potential in cardiovascular diseases, oncology, inflammation, and neurodegenerative diseases. Its anti-platelet aggregation and antithrombotic effects offer new ideas for the prevention and adjunctive treatment of cardiovascular and cerebrovascular diseases. Anti-tumor cytotoxicity and anti-inflammatory activity offer possibilities for treating tumors and chronic inflammatory diseases.
However, the clinical translation of cyanin ketone still faces many challenges. First, limitations in water solubility and bioavailability need to be overcome through drug design and formulation technology. Second, systematic pharmacokinetics and toxicology studies are still lacking, and it is necessary to clarify their metabolic pathways and long-term safety in vivo. Third, in-depth analysis of its multi-target mechanism of action helps optimize treatment plans and precise medication.
In the future, chlorinochromein ketone can combine strategies such as nanocarriers, drug eutectics, and structural modification to enhance its drug properties and targeting. At the same time, systematic research on its mechanisms based on modern molecular biology and omics techniques will promote its advancement toward clinical application. Conducting multicenter clinical trials is also a key step in verifying efficacy and safety.
Chlorogenic ketone, a natural chromogen compound derived from Formosan Peucedanum japonicum, shows broad prospects for drug development due to its remarkable antiplatelet aggregation, anti-tumor, and anti-inflammatory activities. Its multi-target mechanism offers new approaches for treating cardiovascular diseases, tumors, inflammation, and neurodegenerative diseases. Although there are still certain limitations in terms of druggability and pharmacokinetics, with deeper research and technological advancements, eugenanone is expected to become an important candidate in the field of natural product pharmacology. Future research should focus on mechanistic analysis, drug optimization, and clinical validation to promote early clinical application and benefit patients.
Shenshuai
Wenjing
Hedandan
