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Product name: 3,7-Di-O-methylquercetin
Synonym name:
Catalogue No.: SBP03064
Cas No.: 2068-02-2
Formula: C17H14O7
Mol Weight: 330.292
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.
NMR of 3,7-Di-O-methylquercetin
HPLC of 3,7-Di-O-methylquercetin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
118.0600
1.3200
1.3200
Low
No
No
No
No
No
No
3,7-Di-O-methylquercetin (CAS No.: 2068-02-2) is a naturally occurring dimethoxyflavonoid compound, a derivative of quercetin methylated at positions 3 and 7 of hydroxyl groups. As a structural modifier of quercetin, 3,7-bi-O-methylquercetin not only retains various bioactivities of quercetin but also exhibits unique pharmacological properties. In recent years, with in-depth research into the pharmacological mechanisms of natural products, this compound has attracted widespread attention due to its significant antioxidant, anti-inflammatory, antidiabetic, antitumor, and neuroprotective effects. This paper aims to systematically review the chemical structure, origin, pharmacological activity, mechanism of action, druggability, and clinical application potential of 3,7-bi-O-methylquercetin, providing theoretical basis and research directions for further development.
The chemical name of 3,7-bis-O-methylquercetin is 3',4',5-trihydroxy-3,7-dimethoxyflavone, with a molecular formula of C18H16O7 and a molecular weight of 330.29. Its structure is based on a flavonoid backbone, with the hydroxyl groups at positions 3 and 7 of quercetin replaced by methyl groups, forming two methoxy substituents that retain the hydroxyl groups at positions 3', 4', and 5'. Methylation modification of this structure increases the molecule's hydrophobicity (LogP about 1.32) while maintaining a high polar surface area (TPSA of 118.06), achieving a certain balance between cell membrane permeability and water solubility.
In terms of physicochemical properties, 3,7-di-O-methylquercetin exhibits good chemical and thermal stability. Its number of hydrogen bond acceptors is 7, indicating strong hydrogen bonding ability in biomacromolecule binding. The blood-brain barrier penetration ability is relatively low, suggesting that its direct effect in the central nervous system may be limited, but it can still exert neuroprotective effects by modulating peripheral nerves and vascular systems. Toxicological evaluation showed that its acute toxicity was low (LD50 about 2000 mg/kg), with no significant hepatotoxicity, cardiotoxicity, or hERG channel suppression, and the Ames-induced mutagenic test was negative, demonstrating good safety profiles.
3,7-Di-O-methylquercetin is widely found in various plants, especially in plant families rich in quercetin, such as Rosaceae, Asteraceae, and legumes. Its naturally occurring form is mostly in free or glycoside bound form, commonly found in plant leaves, flowers, and fruits. Typical source plants include ginkgo leaves, maple leaves, and certain Chinese medicinal materials such as Scutellaria baicalensis and chinaberry.
The extraction method typically uses organic solvent extraction combined with chromatography separation technology. Common extraction solvents include methanol, ethanol, or ethyl acetate, combined with ultrasound-assisted or microwave-assisted extraction to improve extraction efficiency. After concentration, the extract was purified using silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC), ultimately yielding high-purity 3,7-di-O-methylquercetin. In recent years, green extraction technologies such as supercritical CO2 extraction and deep eutectic solvent extraction have also been applied to extract this compound, balancing environmental protection and efficiency.
3,7-Di-O-methylquercetin, as a polyhydroxyflavonoid compound, demonstrates strong antioxidant capacity. In vitro experiments show that it can effectively eliminate free radicals, inhibit lipid peroxidation, and protect cells from oxidative stress damage. Its antioxidant effects mainly work by activating the nuclear factor E2-related factor 2 (NFE2L2/NRF2) signaling pathway, inducing the expression of downstream antioxidant enzymes such as superoxide dismutase (SOD1, SOD2), catalase peroxidase (CAT), glutathione peroxidase (GPX1), and heme oxygenase 1 (HMOX1), thereby enhancing cellular antioxidant defense capabilities. Additionally, 3,7-bis-O-methylquercetin can regulate matrix metalloproteinase (MMP1, MMP3) activity, slow down the degradation of the extracellular matrix, and protect tissue structure.
Inflammation is the common pathological basis for many chronic diseases. 3,7-Bis-O-methylquercetin exerts anti-inflammatory effects through multi-target regulation. It can inhibit activation of the nuclear factor κB (NFKB1) signaling pathway, reduce the expression of pro-inflammatory factors such as tumor necrosis factor α (TNF), cyclooxygenase-2 (PTGS2), and phospholipase A2 (PLA2G2A), thereby alleviating inflammatory responses. At the same time, this compound also inhibits the mitogen-activated protein kinase (MAPK1) pathway, further suppressing the release of inflammatory mediators, demonstrating potential therapeutic value for various inflammatory diseases such as arthritis, inflammatory bowel disease, and respiratory inflammation.
The pathogenesis of diabetes is complex, involving abnormalities in the insulin signaling pathway and glucose metabolism disorders. 3,7-Di-O-methylquercetin can enhance insulin receptor (INSR) activity, promote the translocation of glucose transporter 4 (SLC2A4) to the cell membrane, and improve glucose uptake efficiency. At the same time, this compound activates AMP-activated protein kinase (PRKAA1) and protein kinase B (AKT1) signaling pathways, regulating energy metabolism and cell survival, thereby improving insulin resistance. Additionally, its regulatory effect on peroxisome proliferator-activated receptor γ (PPARG) helps balance lipid metabolism and alleviates diabetes-related metabolic disorders.
3,7-Di-O-methylquercetin exhibits effects in various tumor cells by inhibiting proliferation, inducing apoptosis, and suppressing metastasis. Its targets include epidermal growth factor receptor (EGFR), vascular endothelial growth factor receptor (KDR), anti-apoptotic protein B-cell lymphoma-2 (BCL2), tumor suppressor protein p53 (TP53), and phosphatidyl-inositol 3-kinase (PIK3CA). By modulating these signaling pathways, 3,7-bi-O-methylquercetin can block tumor cell growth signals, promote cell cycle arrest and apoptosis, inhibit tumor angiogenesis and metastasis, and demonstrates good anti-tumor potential.
The pathogenesis of neurodegenerative diseases such as Alzheimer's and Parkinson's is closely related to oxidative stress, inflammation, and abnormal protein aggregation. 3,7-Di-O-methylquercetin reduces the accumulation of neurotoxic proteins by regulating abnormal expression of β-amyloid protein precursor protein (APP) and tau protein (MAPT). It activates the NFE2L2 signaling pathway, enhances antioxidant enzyme activity, and alleviates oxidative stress damage. At the same time, it inhibits acetylcholinesterase (ACHE) activity, improves neurotransmitter function, and demonstrates protective effects on cognitive function. Its application prospects in neurodegenerative disease models are broad.
The multi-target mechanism of 3,7-bi-O-methylquercetin forms the basis for its various pharmacological activities. It modulates intracellular signaling networks by directly binding to or regulating key enzymes, receptors, and transcription factors.
Additionally, 3,7-di-O-methylquercetin, as an EC 1.3.1.22 (3-oxo-5α-steroid 4-dehydrogenase) inhibitor, may affect steroid metabolism, further regulate intracellular signaling environment, and enhance its pharmacological effects.
The druggability parameters of 3,7-bis-O-methylquercetin indicate that it has promising potential for drug development. The molecular weight is moderate (330.29 Da), with a LogP value of 1.32, indicating suitable lipid solubility and favorable penetration of cell membranes. TPSA is 118.06, indicating a certain polarity, which helps balance water solubility and bioavailability. It has 7 hydrogen bond receptors, meeting the requirements for drug molecules to bind to target proteins.
Toxicological evaluation showed that the compound was safe, had low acute toxicity, no significant hepatic or cardiac toxicity, and did not affect the hERG channel, reducing the risk of arrhythmias. The Ames test was negative, indicating no risk of mutagenic inducement.
In terms of pharmacokinetics, although the blood-brain barrier penetration ability is relatively low, it is well distributed in peripheral tissues, making it suitable for treating inflammation, metabolism, and tumor-related diseases. Compared to quercetin, its methylation modification improves metabolic stability and reduces the issue of reduced bioavailability caused by rapid metabolism. However, the specific characteristics of absorption, distribution, metabolism, and excretion (ADME) still require further in vivo pharmacokinetic studies to clarify them.
Based on the broad-spectrum pharmacological activity of 3,7-di-O-methylquercetin in various disease models, its clinical application prospects are broad. Its antioxidant and anti-inflammatory properties give it potential therapeutic value in chronic inflammatory diseases, cardiovascular diseases, and metabolic syndromes. Its ability to regulate insulin signaling pathways offers new ideas for adjunctive treatment of diabetes and its complications.
Its antitumor activity makes it a strong candidate for adjuvant therapy, especially showing advantages in inhibiting tumor growth and metastasis. Neuroprotective effects provide new drug resources for the treatment of neurodegenerative diseases such as Alzheimer's disease.
Future research should focus on:
Moreover, combining modern drug design technologies, such as computer-aided drug design (CADD) and nanodrug carrier technology, is expected to accelerate the drug development process for 3,7-bi-di-O-methylquercetin.
3,7-Di-O-methylquercetin, as a methylated derivative of quercetin, combines the multiple bioactivities of natural flavonoid compounds with excellent safety profiles. It demonstrates broad application potential in fields such as antioxidant, anti-inflammatory, anti-diabetic, anti-tumor, and neuroprotective properties. Through in-depth study of its mechanism of action and optimized pharmacokinetic performance, 3,7-bis-di-O-methylquercetin is expected to become an important natural drug candidate for multi-target disease treatment in the future. With the continuous advancement of natural product pharmacology and modern drug development technologies, the clinical translation prospects of this compound are promising.
Shenshuai
Wenjing
Hedandan
