437-64-9
4',5-Dihydroxy-7-methoxyflavone
CAS: 437-64-9
Molecular Formula: C16H12O5
437-64-9 - Names and Identifiers
| Name | 4',5-Dihydroxy-7-methoxyflavone |
| Synonyms | Genkwanin Gengkwanin 4H-Benzopyran-4-one 5,4'-DIHYDROXY-7-METHOXYFLAVONE 4',5-DIHYDROXY-7-METHOXYFLAVONE 4',5-Dihydroxy-7-methoxyflavone 2-(4-Hydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one 4H-1-Benzopyran-4-one,5-hydroxy-2-(4-hydroxyphenyl)-7-Methoxy- 4',5-Dihydroxy-7-methoxyisoflavone 5,4'-Dihydroxy-7-methoxyisoflavone |
| CAS | 437-64-9 |
| InChI | InChI=1/C16H12O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3 |
437-64-9 - Physico-chemical Properties
| Molecular Formula | C16H12O5 |
| Molar Mass | 284.26 |
| Density | 1.420 |
| Melting Point | 290-292°C |
| Boling Point | 546.5±50.0 °C(Predicted) |
| Solubility | Soluble in hot methanol, DMSO and other solvents. |
| Appearance | Yellow needle crystal |
| Color | Orange |
| BRN | 292549 |
| pKa | 6.36±0.40(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,2-8°C |
| Stability | Hygroscopic |
| MDL | MFCD00017452 |
| Physical and Chemical Properties | Soluble in hot methanol, DMSO and other solvents. Flower buds from Daphne genkwa Sieb. et Zucc. |
| In vitro study | Cell viability analysis shows that Genkwanin does not affect the cell viability up to a concentration of 50 μM. Genkwanin inhibits the LPS-induced production of NO in a concentration-dependent manner. iNOS only expresses in the present of external stimulus. Genkwanin could not significantly affect the activity of iNOS. The effect of Genkwanin on the production of proinflammatory cytokines is examined. Genkwanin suppresses the productions of TNF-a, IL-1b and IL-6 in LPS stimulated RAW264.7 macrophages in a concentration-dependent manner. Genkwanin significantly suppresses the AP-1 signaling pathway but has little effect on the NF-kB signaling pathway. It is indicated that Genkwanin suppresses the phosphorylation of p38 and JNK in a concentration-dependent manner, but little affects ERK1/2 phosphorylation. Originally identified as an immediate early gene, MKP-1 is then found to be a dual specificity phosphatase acting as a negative regulator of ERK1/2, JNK and p38 MAPK activities, with predominant effects on the latter two. Pretreatment with Genkwanin markedly up-regulates the expression of MKP-1 without affecting MKP-1 mRNA. |
437-64-9 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R22 - Harmful if swallowed |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S24/25 - Avoid contact with skin and eyes. S22 - Do not breathe dust. S37 - Wear suitable gloves. |
| HS Code | 29329990 |
437-64-9 - Reference
| Reference Show more | 1. [IF=6.576] Junkun Pan et al."Inhibition of Dipeptidyl Peptidase-4 by Flavonoids: Structure–Activity Relationship, Kinetics and Interaction Mechanism."Frontiers in Nutrition. 2022; 9: 892426 |
437-64-9 - Reference Information
| Overview | Genkanin (Genkwanin) is also known as Genkanlutein, and its chemical name is 5,4 '-dihydroxy-7-methoxyflavone, which is one of the flavonoids. In 1932, Mr. Zeng Guangfang, a natural medicinal chemist in China, cooperated with Japanese scholar Nakao Wansan to isolate genkwadin and apigenin from the genkwadin sold in Shanghai for the first time, and determined the structure of genkwadin. Daphne genkwa Sieb.et Zucc is a plant of the family Daphne genkwa. The dry buds. Distributed in Fujian, Zhejiang, Jiangsu, Anhui, Hubei, Hunan and other places. Genkwa has the effect of purging water and drinking, detoxifying and killing insects. Mainly used for the treatment of edema and fullness, chest and abdomen hydrops, accumulation of phlegm, dyspnea cough, adverse stool and other symptoms. External use can treat scabies, baldness, frostbite. Clinical vinegar is used or used raw for vinegar genkwa flowers. The root bark of the genkwa has the effect of "giving birth to the fetus", which is used by the Chinese people to induce labor. Its leaves can treat toothache and vivax malaria. The main components of Genkwa are Genkwa (Genkwanin), apigenin (Apigenin), 3 '-hydroxyGenkwa (3'-Hydroxygenkwanin), Genkwa glycoside (Yuankanin), luteolin (Luteolin), Genkwa Ruixiangning (Genkwadaphnin), Genkwa ester A (Genkwa terpene, yuanhuacine), Genkwa Ester B (Yuanhuadine), Genkwa Ester C (Yuanhuafine), Genkwa Ester D (Yuanhuatine), Genkwa Ester C (Yuanhuapine). Volatile oils include palmitic acid, oleic acid, linoleic acid, etc. It also contains sitosterol, benzoic acid and toxic oil. Genkanin also has antioxidant, anti-tumor, anti-inflammatory and analgesic effects, and less toxic and side effects. |
| synthesis method | the low content and low extraction rate of genkwa in natural drugs are difficult to meet the growing market demand. Therefore, it is very necessary to research and develop effective and practical synthetic methods of genkhuanin. (2016-01-13) |
| biological activity | Genkwanin (genkalen) is an O-methylated flavone with anti-inflammatory activity. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effect: can inhibit the movement of isolated intestine and uterus. |
Last Update：2024-04-09 21:54:55
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