- 7,8-Dihydroxyflavone
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- $90.00 / 100mg
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2025-10-26
- CAS:38183-03-8
- Min. Order:
- Purity: 99.81%
- Supply Ability: 10g
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| | 7,8-Dihydroxyflavone Basic information |
| Product Name: | 7,8-Dihydroxyflavone | | Synonyms: | 7,8-DIHYDROXYFLAVONE;7,8-dihydroxy-2-phenyl-4-benzopyrone;DIHYDROXYFLAVONE, 7,8-(RG);7,8-Dihydroxyflavone hydrate;7,8-dihydroxy-2-phenyl-1-benzopyran-4-one;8-Dihydroxyflavone;7,8-DIHYDROXYFLAVONE 7,8-DIHYDROXYFLAVONE;7,8-dihydroxy-2-phenyl-4h-1-benzopyran-4-on | | CAS: | 38183-03-8 | | MF: | C15H10O4 | | MW: | 254.24 | | EINECS: | 253-812-4 | | Product Categories: | Inhibitors;Biochemistry;Flavonoids;Di-substituted Flavones;pharmaceutical;BPC;plant extract | | Mol File: | 38183-03-8.mol |  |
| | 7,8-Dihydroxyflavone Chemical Properties |
| Melting point | 243-246°C | | Boiling point | 494.4±45.0 °C(Predicted) | | density | 1.443±0.06 g/cm3(Predicted) | | FEMA | 4830 | 7,8-DIHYDROXYFLAVONE | | storage temp. | Inert atmosphere,Room Temperature | | solubility | DMSO: soluble24mg/mL | | form | solid | | pka | 6.86±0.40(Predicted) | | color | Yellow or tan | | Stability: | Stable for 1 year from date of purchase as supplied. Protect from moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 week. | | InChI | InChI=1S/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H | | InChIKey | COCYGNDCWFKTMF-UHFFFAOYSA-N | | SMILES | C1(C2=CC=CC=C2)OC2=C(O)C(O)=CC=C2C(=O)C=1 | | LogP | 2.760 (est) | | CAS DataBase Reference | 38183-03-8(CAS DataBase Reference) |
| Hazard Codes | Xn | | Risk Statements | 22 | | Safety Statements | 24/25 | | WGK Germany | 3 | | RTECS | DJ3004000 | | HS Code | 2932990090 |
| | 7,8-Dihydroxyflavone Usage And Synthesis |
| Description | 7,8-Dihydroxyflavone(7,8-DHF) is a naturally occurring flavone found in the tree Godmania aesculifolia. It is a selective tyrosine kinase receptor B(TrkB) agonist that has neurotrophic effects in various neurological diseases such as stroke and Parkinson's disease. 7,8-Dihydroxyflavone binds to the TrkB receptors in a similar way to BDNF, or brain derived neurotrophic factor. When the TrkB receptor is activated, neuroprotective and neurogenetive effects occur in neurons, which tend to affect the dendrites. Dendrites are what reach out from the neurons into the synapse to participate in signaling with other neurons. 7,8-DHF has been shown to promote the growth of these dendrites, and to help restore communication between neurons in animal models. | | Chemical Properties | White crystalline powder or Yellow Solid, soluble in methanol, ethanol, DMSO and other organic solvents, from the dried root of Pulsatilla chinensis (Bge.) Regel. | | Uses | 7,8-Dihydroxyflavone is disubstituted flavone that acts as a small-molecule TrkB agonist. 7,8-Dihydroxyflavone has been shown to reverse memory deficits and BACE1 elevation in a mouse model of Alzheimer''s disease. 7,8-Dihydroxyflavone may also provide a therapeutic option in the treatment of other neorological disorders such as Rett syndrome and PTSD. It has recently been shown to counteract the inhibition of NMDA receptor caused by lead poisoning and confer protective effects in live rats. | | Definition | ChEBI: 7,8-dihydroxyflavone is a dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A dihydroxyflavone that is flavone substituted by hydroxy groups at positions 7 and 8. A naturally occurring flavonoid produced by several plants, including the weed Tridax procumbens (coalbuttons or tridax daisy) and the tree Godmania aesculifolia, In animal models, it has shown efficacy against several diseases of the nervous system, including Alzheimer's, Parkinson's, and Huntington's. It has a role as a plant metabolite, a tropomyosin-related kinase B receptor agonist, an antidepressant, an antioxidant and an antineoplastic agent. | | Biological Activity | 7,8-Dihydroxyflavone (7,8-DHF) is a monophenolic flavone with diverse effects. It acts as an agonist of the neurotrophic tyrosine kinase receptor TrkB (Kd = 320 nM), protecting neurons that express TrkB from apoptosis. 7,8-DHF is neuroprotective in an animal model of Parkinson’s disease. It supports emotional learning in mice and reverses memory deficits in a mouse model of Alzheimer’s disease. It also improves motor function and extends survival in an animal model of Huntington’s disease. 7,8-DHF inhibits the cytochrome P450 aromatase (IC50 = 10 μM) and, in this way, alters estrogen metabolism. It also has antioxidant action that increases intracellular glutathione synthesis and scavenges reactive oxygen species. | | Biochem/physiol Actions | 7,8-Dihydroxyflavone is a selective tyrosine kinase receptor B (TrkB) receptor agonist. It manifests all the therapeutic effects of brain-derived neurotrophic factor (BDNF)—such as protecting neurons from apoptosis, inhibiting kainic acid-induced toxicity, decreasing infarct volumes in stroke, and neuroprotecting in an animal model of Parkinson′s disease—without the poor pharmacokinetic profile of BDNF limiting its therapeutic potential. | | Side effects | As with any other drug, 7,8-DHF is not without its side effects. However, there are not as many side effects associated with the use of 7,8-DHF as it is a natural product.
The following are some reported side effects associated with the use of 7,8-DHF or products that contain it:
Overstimulation
Restlessness
Dizziness
Nausea
Irritability
Trouble sleeping | | Synthesis | GENERAL METHOD: Compound 10a (4.3 g, 10.0 mmol) or 10b (5.4 g, 10.0 mmol) was dissolved in THF/CH3OH (40.0 mL/40.0 mL) mixed solvent and 10% Pd/C (0.5 g) was added. The reaction mixture was stirred overnight under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (6:1, v/v) as eluent to give the target product 11a or 11b. | | target | TNF-α | MMP(e.g.TIMP) | ROS | HO-1 | p38MAPK | SOD | Akt | cAMP | HIF | PPAR | Calcium Channel | | storage | Store at +4°C | | Mode of action | 7,8-Dihydroxyflavone (7,8-DHF, tropoflavin) is the most common and effective flavone identified in Sophora plants.
7,8-DHF mimics the effects of brain-derived neurotrophic factor (BDNF) in brain cells by activating tropomyosin-related kinase B (TrkB) receptors, the typical target of BDNF.
The therapeutic potential of BDNF is restricted due to its short half-life (less than 10 minutes) and its inability to cross the blood-brain barrier because of its large size. Unlike BDNF 7,8-DHF is able to penetrate the blood-brain barrier and enter the central nervous system (CNS) .
7,8-DHF also increases the production of Nrf2. Nrf2 increases antioxidants enzymes such as heme oxygenase 1 (HO-1) and also enzymes that repair DNA (8-oxoguanine DNA glycosylase-1 – OGG1) . | | References | [1] SUNG-WUK JANG. A selective TrkB agonist with potent neurotrophic activities by 7,8-dihydroxyflavone.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2010, 107 6: 2687-2692. DOI:10.1073/pnas.0913572107
[2] XIA LIU. Biochemical and biophysical investigation of the brain-derived neurotrophic factor mimetic 7,8-dihydroxyflavone in the binding and activation of the TrkB receptor.[J]. The Journal of Biological Chemistry, 2014, 289 40: 27571-27584. DOI:10.1074/jbc.m114.562561
[3] MALI JIANG. Small-molecule TrkB receptor agonists improve motor function and extend survival in a mouse model of Huntington’s disease.[J]. Human molecular genetics, 2013: 2462-2470. DOI:10.1093/hmg/ddt098
[4] SHU ZHAO. Post-Injury Treatment of 7,8-Dihydroxyflavone Promotes Neurogenesis in the Hippocampus of the Adult Mouse.[J]. Journal of neurotrauma, 2016, 33 22 1: 2055-2064. DOI:10.1089/neu.2015.4036
[5] ORHAN TANSEL KORKMAZ . 7,8-Dihydroxyflavone improves motor performance and enhances lower motor neuronal survival in a mouse model of amyotrophic lateral sclerosis[J]. Neuroscience Letters, 2014, 566: Pages 286-291. DOI:10.1016/j.neulet.2014.02.058 |
| | 7,8-Dihydroxyflavone Preparation Products And Raw materials |
| Raw materials | 4H-1-Benzopyran-4-one, 2-phenyl-7,8-bis(phenylmethoxy)--->4H-1-Benzopyran-4-one, 7,8-bis(benzoyloxy)-2-phenyl--->Ethanone, 1-[2,3,4-tris(phenylmethoxy)phenyl]--->Ethanone, 1-[2-hydroxy-3,4-bis(phenylmethoxy)phenyl]--->7,8-DIMETHOXYFLAVONE-->2'-HYDROXY-3',4'-DIMETHOXYACETOPHENONE-->2',3',4'-TRIHYDROXYACETOPHENONE-->7-HYDROXYFLAVONE-->Pyrogallol-->Benzoic anhydride-->Benzoyl chloride |
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