Product name: Tetramethylkaempferol
Synonym name: Tetramethoxyflavone
Catalogue No.: BP4650
Cas No.: 16692-52-7
Formula: C19H18O6
Mol Weight: 342.347
Botanical Source:
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 Tetramethylkaempferol
NMR of Tetramethylkaempferol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Tetramethylkaempferol (CAS No.: 16692-52-7), a natural flavonoid compound, has attracted widespread attention in recent years due to its unique biological activity. Flavonoids are commonly found in various plants and possess diverse pharmacological effects, such as antioxidant, anti-inflammatory, antibacterial, and antitumor properties. Tetramethylphylamine, as a methylated derivative of kaempol, demonstrated excellent antifungal activity, especially showing significant inhibitory effects against Candida albicans, with an IC50 value of 17.63 μg/mL. Moreover, its potential role in antioxidant properties has attracted significant attention from the pharmacological community, with related targets covering various key enzymes and transcription factors such as NFE2L2 (NRF2), SOD1, and CAT. This paper aims to systematically review the chemical structure, origin, pharmacological activity, mechanism of action, and druggability evaluation of tetramethylkasanol, exploring its potential and development prospects in clinical applications.
Tetramethylkapinol belongs to the flavonoid class of compounds, with a molecular formula of C18H18O7 and a molecular weight of 342.3470. Its structure is based on the kaempol framework, modified by four methyl substitutions, significantly affecting its physicochemical properties and biological activity. The compound has a LogP value of 3.0279, indicating moderate lipid solubility, which facilitates cell membrane penetration and distribution in vivo. The polar surface area (TPSA) is 67.13 Ų, indicating that it contains certain polar groups that help solubility in the aqueous phase and bind to targets. Low water solubility (0.0048 mg/mL) suggests limited solubility in the aqueous phase, which may affect oral bioavailability. Notably, tetramethylkasanol has a high blood-brain barrier penetration ability, suggesting its potential application value in central nervous system diseases. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames mutagenic test scored 0.9, indicating a low genotoxicity risk and good safety.
Tetramethylkapinol is mainly found in various traditional medicinal plants, especially certain plants rich in kaempaboloid flavonoids. Common sources include certain legumes, Asteraceae plants, and some woody plants. Its content is greatly influenced by plant species, growing environment, and harvest time. The extraction method mostly uses organic solvent extraction combined with column chromatography separation technology. Common extraction solvents include methanol, ethanol, and ethyl acetate, which can effectively extract flavonoid compounds. The extraction process typically includes crushing plant material, solvent extraction, concentration, liquid-liquid distribution, and silica gel column chromatography purification. In recent years, emerging technologies such as ultrasound-assisted extraction and microwave-assisted extraction have been applied to improve extraction efficiency and purity. In addition, high-performance liquid chromatography (HPLC) and mass spectrometry (LC-MS) techniques are widely used for qualitative and quantitative analysis of tetramethylkasanol.
One of the most notable pharmacological activities of tetramethylphyllol is its inhibitory effect on fungi, especially Candida albicans. In vitro experiments showed that its IC50 for Candida albicans was 17.63 μg/mL, indicating strong antifungal activity. This activity makes it a potential candidate molecule for antifungal drug development. Compared to traditional antifungal drugs, tetramethylkaempol may act through a different mechanism, showing promise in overcoming the resistance issues of existing drugs.
Tetramethylkaemprol exerts protective effects by modulating various antioxidant-related targets. Its targets include tyrosinase (TYR), matrix metalloproteinases (MMP1, MMP3), nuclear factor E2-related factor 2 (NFE2L2/NRF2), superoxide dismutase (SOD1, SOD2), catalase (CAT), glutathione peroxidase (GPX1), and heme oxygenase 1 (HMOX1). These targets play a key role in cellular oxidative stress responses. Tetramethylphysanol activates the NRF2 signaling pathway, promotes antioxidant enzyme expression, reduces oxidative damage, prevents free radical-mediated cell damage, and has potential value in anti-aging and the prevention and treatment of oxidation-related diseases.
In addition to antifungal and antioxidant effects, preliminary studies suggest that tetramethylkamarol may possess multiple pharmacological activities, including anti-inflammatory, anti-tumor, and neuroprotective effects. Its high blood-brain barrier permeability offers possibilities for drug development for neurological diseases, but related research is still in its infancy and requires further in-depth exploration.
The antifungal mechanism of tetramethylkaemprol is not yet fully elucidated, but it is hypothesized that it inhibits fungal cell wall synthesis or influences fungal metabolic pathways by interfering with the structure and function of fungal cell membranes. Combined with its flavonoid structure, it may regulate the oxidative state within fungal cells through redox reactions, inducing apoptosis.
In terms of antioxidant activity, tetramethylkamarol activates the NFE2L2/NRF2 signaling pathway, promoting the expression of downstream antioxidant enzymes such as SOD1, CAT, GPX1, and HMOX1, enhancing cells' ability to scavenge reactive oxygen species (ROS), and reducing cellular damage caused by oxidative stress. Additionally, its regulatory effects on MMP1 and MMP3 help maintain the stability of the extracellular matrix and prevent tissue damage and inflammatory responses caused by oxidative stress.
Molecular docking and in vitro experiments have shown that tetramethylkanapol can form stable binding with multiple target proteins, regulate their activity, and further support its multi-target, multi-pathway pharmacological mode of action.
The druggability evaluation of tetramethylphynamol shows it has promising potential for drug development. The LogP value is 3.0279, meeting the lipid solubility requirements in the Lipinski rule, which is beneficial for oral absorption. TPSA is 67.13 Ų, indicating suitable polarity and balancing lipid and water solubility. Lower water solubility may limit its oral bioavailability, but improvements in formulations such as nanocarriers and liposomes are expected to overcome this.
Its high blood-brain barrier penetration capability makes treatment of central nervous system diseases possible. The negative results for hERG channel inhibition reduced the risk of cardiotoxicity, while Ames assay results showed that the genotoxicity risk was lower and the safety was good.
Currently, pharmacokinetic data on tetramethylkasanol are limited. It is preliminarily speculated that it has good distribution characteristics in the body, but its metabolic pathways and excretion mechanisms still require systematic study. In the future, in vivo pharmacokinetic studies are needed to clarify its absorption, distribution, metabolism, and excretion (ADME) characteristics, laying a foundation for clinical application.
Tetramethylphylaquinol, as a natural flavonoid compound, demonstrates broad clinical application prospects due to its remarkable antifungal activity and multi-target antioxidant effects. Its inhibitory effect on Candida albicans provides new ideas for antifungal drug development, especially in the context of increasingly severe antifungal resistance, and holds significant clinical value.
Its antioxidant activity gives it potential application value in preventing and treating oxidative stress-related diseases such as cardiovascular diseases, neurodegenerative diseases, and inflammatory diseases. High blood-brain barrier permeability makes its application possible in central nervous system diseases such as Alzheimer's and Parkinson's disease.
Future research should focus on deeply analyzing its mechanisms, optimizing extraction and synthesis processes, and improving purity and yield; Systematic pharmacokinetic and toxicological studies are also conducted to evaluate safety and efficacy. By integrating modern drug delivery systems, it enhances its bioavailability and targeting, promoting its clinical translation.
Additionally, due to its multi-target effect, tetramethylsnamol is expected to serve as a multifunctional drug or combination drug component, achieving synergistic therapeutic effects and expanding its clinical indications.
Tetramethylphylaquinol, as a natural flavonoid compound with significant antifungal and antioxidant activity, demonstrates excellent druggability and broad clinical application prospects due to its unique chemical structure and multi-target mechanism. Although research on its pharmacological mechanisms and pharmacokinetics is not yet comprehensive, existing research has laid a solid foundation for its development as a novel antifungal drug and antioxidant therapy. In the future, it is necessary to strengthen basic and applied research, optimize formulation technologies, promote their transformation into clinical applications, and contribute new drug resources and therapeutic strategies to the field of natural product pharmacology.
