7,8-Dihydroxyflavone

Base Information

• Chemical Name: 7,8-Dihydroxyflavone
• CAS No.: 38183-03-8
• Molecular Formula: C15H10O4
• Molecular Weight: 254.242
• Hs Code.: 2914400090
• European Community (EC) Number: 253-812-4
• NSC Number: 750341
• UNII: ADB6MA8ZV2
• DSSTox Substance ID: DTXSID00191568
• Nikkaji Number: J294.607F
• Wikipedia: Tropoflavin
• Wikidata: Q19596931
• Metabolomics Workbench ID: 74509
• ChEMBL ID: CHEMBL75267
• Mol file: 38183-03-8.mol

Synonyms:6,7-dihydroxyflavone;7,8-dihydroxyflavone

Chemical Property of 7,8-Dihydroxyflavone

Chemical Property:

• Vapor Pressure: 2.13E-10mmHg at 25°C
• Melting Point: 243-246°C
• Refractive Index: 1.698
• Boiling Point: 494.4 °C at 760 mmHg
• PKA: 6.86±0.40(Predicted)
• Flash Point: 193.5 °C
• PSA: 70.67000
• Density: 1.443 g/cm³
• LogP: 2.87120
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: soluble24mg/mL
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 254.05790880
• Heavy Atom Count: 19
• Complexity: 384

Purity/Quality:

99%, ^*data from raw suppliers

7,8-Dihydroxyflavone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O
• 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.
• 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.

Technology Process of 7,8-Dihydroxyflavone

There total 27 articles about 7,8-Dihydroxyflavone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

7-hydroxyflavone (6665-86-7,66585-10-2) → 7,8-dihydroxyflavone (38183-03-8)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 80 ℃; for 24h;

DOI:10.1016/j.tet.2010.06.014

Reference yield: 90.5%

C29H22O4 (500866-00-2) → 7,8-dihydroxyflavone (38183-03-8)

Guidance literature:

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; methanol; at 40 ℃; under 4560.31 - 6080.41 Torr;

Reference yield: 63.0%

C29H18O6 (110865-10-6) → 7,8-dihydroxyflavone (38183-03-8)

Guidance literature:

With sodium methylate; In ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)85249-1

upstream raw materials:

7-hydroxyflavone

8-acetyl-7-hydroxy-2-phenyl-chromen-4-one

1-(3,4-bis-benzoyloxy-2-hydroxy-phenyl)-3-phenyl-propane-1,3-dione

ethyl 3-oxo-3-phenylpropionate

Downstream raw materials:

8-phenyl-[1,3]dioxolo[4,5-h]chromen-6-one

4-oxo-2-phenyl-4H-chromene-7,8-diyl diacetate

4-oxo-2-phenyl-4H-chromene-7,8-diyl Bis(trifluoromethanesulfonate)

7,8-bis-(1,1-dimethyl-allyloxy)-2-phenyl-4H-chromen-4-one

Refernces

• 1、 -. "Preparation method of 7,8-dihydroxy flavone". . . Retrieved 2020/07/13.
• 2、 Ravishankar, Divyashree,Watson, Kimberly A.,Greco, Francesca,Osborn, Helen M. I.. "Novel synthesised flavone derivatives provide significant insight into the structural features required for enhanced anti-proliferative activity". . p. 64544 - 64556. Retrieved 2016/07/21.