Kaempferol tetramethyl ether
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| Category | Others |
| Catalog number | BBF-04993 |
| CAS | 16692-52-7 |
| Molecular Weight | 342.34 |
| Molecular Formula | C19H18O6 |
| Purity | ≥95% |
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Description
Kaempferol tetramethyl ether, a natural product found in Bryobium eriaeoides and Meistera koenigii, is a PPARγ agonist that can improve insulin sensitivity by increasing the levels of adiponectin.
Specification
| Synonyms | Tetramethylkaempferol; 4H-1-Benzopyran-4-one, 3,5,7-trimethoxy-2-(4-methoxyphenyl)-; 3,5,7-Trimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one; Flavone, 3,4',5,7-tetramethoxy-; 2-(4-Methoxyphenyl)-3,5,7-trimethoxy-4-oxo-4H-1-benzopyran; 3,4',5,7-Tetramethoxyflavone; 3,5,7,4'-Tetra-O-methylkaempferol; 3,5,7,4'-Tetramethoxyflavone; 3,5,7-Trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one; O-Tetramethylkaempferol |
| Storage | Store at -20°C |
| IUPAC Name | 3,5,7-trimethoxy-2-(4-methoxyphenyl)chromen-4-one |
| Canonical SMILES | COC1=CC=C(C=C1)C2=C(C(=O)C3=C(O2)C=C(C=C3OC)OC)OC |
| InChI | 540.6±50.0°C at 760 mmHg |
| InChI Key | YZWIIEJLESXODL-UHFFFAOYSA-N |
Properties
| Appearance | Powder |
| Boiling Point | 540.6±50.0°C at 760 mmHg |
| Melting Point | 153°C |
| Density | 1.29±0.1 g/cm3 |
| Solubility | Soluble in Acetone, Chloroform, Dichloromethane, DMSO, Ethyl Acetate |
Reference Reading
1. Bridelia ferruginea Benth.; An ethnomedicinal, phytochemical, pharmacological and toxicological review
Genevieve Naana Yeboah, Frederick William Akuffo Owusu, Mary-Ann Archer, Michael Odoi Kyene, Doris Kumadoh, Frederick Ayertey, Susana Oteng Mintah, Peter Atta-Adjei Junior, Alfred Ampomah Appiah Heliyon. 2022 Aug 23;8(8):e10366. doi: 10.1016/j.heliyon.2022.e10366. eCollection 2022 Aug.
Ethnopharmacological relevance: Bridelia ferruginea belonging to the family Euphorbiaceae, identified as an important commonly growing shrub, is used in traditional medicine for managing arthritis, dysentery, constipation, chronic diabetes, skin diseases, bladder and intestinal disorders, oral infections, thrush, bites and as an arrow poison antidote. This review aims at providing information on the traditional medicinal uses, pharmacological activities, phytochemistry and toxicity studies of Bridelia ferruginea to bridge the gap between traditional medicinal uses and preclinical studies on B. ferruginea and subsequently lead to the development of valued added medicines from B. ferruginea. Materials and methods: Data in this review were compiled using databases such as Google Scholar, Science Direct, Scopus, PubMed, Springer link, Elsevier and Taylor and Francis, articles from peer reviewed journals and other grey literature (short notes, book chapters, short communications) to access all the relevant information available on B. ferruginea. Results: B. ferruginea contains different phytochemicals including flavonoids, phenolics, phytosterols, triterpenes, saponins, alkaloids and cardiac glycosides. Gallocatechin-(4'-O-7)-epigallocatechin, 3,5-dicaffeoylquinic acid, 1,3,4,5-tetracaffeoylquinic acid and some derivatives of 3-methoxyflavone, such as quercetin-3-methyl ether, quercetin 3-,7,3',4'-tetramethyl ether, myricetin 3',4',5'-trimethyl ether, myricetin 3,3',4',5'-tetramethyl ether, myricetin and quercetin 3-O-glucoside specific flavonoids and biflavonoids like apigenin, kaempferol and glycosides of both have been isolated and further characterized from B. ferruginea. B. ferruginea has several pharmacologically beneficial properties including anti-inflammatory, anti-diabetic, antioxidant, antimicrobial, anti-infective, antipyretic, analgesic, diuretic and natriuretic activities. Conclusion: The wide distribution, traditional medicinal uses and wealth of phytochemicals present in B. ferruginea suggests that the plant can be useful in lead compound discovery. Although B. ferruginea has been widely studied, further studies on the mechanism of action, bioavailability, pharmacokinetics, toxicity and side effects in humans need to be investigated.
2. Flavonoid Constituents and Alpha-Glucosidase Inhibition of Solanum stramonifolium Jacq. Inflorescence with In Vitro and In Silico Studies
Sukanya Dej-Adisai, Oraphan Sakulkeo, Chatchai Wattanapiromsakul, Thanet Pitakbut Molecules. 2022 Nov 24;27(23):8189. doi: 10.3390/molecules27238189.
Solanum stramonifolium Jacq. (Solanaceae) is widely found in South East Asia. In Thailand, it is used as vegetable and as a component in traditional recipes. The results of an alpha-glucosidase inhibitory screening test found that the crude extract of S. stramonifolium inflorescence exhibited the potential effect with IC50 81.27 μg/mL. The separation was performed by the increasing solvent polarity method. The ethyl acetate, ethanol, and water extracts of S. stramonifolium inflorescence showed the synergistic effect together with acarbose standard. The phytochemical investigation of these extracts was conducted by chromatographic and spectroscopic techniques. Six flavonoid compounds, myricetin 3, 4', 5', 7-tetramethyl ether (1), combretol (2), kaempferol (3), kaempferol 7-O-glucopyranoside (4), 5-hydroxy 3-7-4'-5'-tetramethoxyflavone-3'-O-glucopyranoside (5), and a mixture (6) of isorhamnetin 3-O-glucopyranoside (6a) and astragalin (6b) were isolated. This discovery is the first report of flavonoid-glycoside 5. Moreover, the selected flavonoids, kaempferol and astragalin, were representatives to explore the mechanism of action. Both of them performed mixed-type inhibition. The molecular docking gave a better understanding of flavonoid compounds' ability to inhibit the alpha-glucosidase enzyme.
3. Geographical variation in the surface flavonoids of Pulicaria dysenterica
CA Williams, JB Harborne, J Greenham Biochem Syst Ecol. 2000 Aug 1;28(7):679-687. doi: 10.1016/s0305-1978(99)00104-0.
Four chemical races were detected in Pulicaria dysenterica, when sampled within Europe, on the basis of the surface flavonoids present. One race uniquely contained quercetagetin 3,7-dimethyl ether and another 6-hydroxykaempferol 3,4'-dimethyl ether. A third race was based on plants having 6-hydroxykaempferol 3,7-dimethyl ether together with quercetagetin 3,7,3'-trimethyl ether. The fourth race contained the above two compounds, as well as quercetagetin 3,7,3',4'-tetramethyl ether and 6-hydroxykaempferol 3,7,4'-trimethyl ether. These lipophilic constituents were variously present on the surfaces of leaf, ray floret, disc floret and fruit. By contrast, the vacuolar flavonoid of all tissues and all races was uniformly quercetin 3-glucuronide. The kaempferol 3-glucoside previously reported in flowers was not detected. Of the lipophilic flavonoids newly reported from this plant, one 6-hydroxykaempferol 3,7,4'-trimethyl ether is new to nature.
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Bio Calculators
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