7,8-DIHYDROXYFLAVONE
- Iupac Name：7,8-dihydroxy-2-phenylchromen-4-one
- CAS No.: 38183-03-8
- Molecular Weight：254.2375
- Modify Date.: 2022-11-22 19:07
- Introduction: 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.
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1. Names and Identifiers
- 1.1 Name
- 7,8-DIHYDROXYFLAVONE
- 1.2 Synonyms
4H-1-Benzopyran-4-one, 7,8-dihydroxy-2-phenyl- 7,8-dihydroxy-2-phenyl-1-benzopyran-4-one 7,8-dihydroxy-2-phenyl-4-benzopyrone 7,8-dihydroxy-2-phenyl-4h-1-benzopyran-4-on 7,8-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one 7,8-Dihydroxy-2-phenyl-4H-chromen-4-one 7,8-dihydroxy-2-phenylchromen-4-one 7,8-DIHYDROXYFLAVONE 7,8-Dihydroxyflavone Hydrate 8-Dihydroxyflavone DIHYDROXYFLAVONE, 7,8-(RG) EINECS 253-812-4 Flavone, 7,8-dihydroxy- MFCD00006836
- 1.3 CAS No.
- 38183-03-8
- 1.4 CID
- 1880
- 1.5 EINECS(EC#)
- 253-812-4
- 1.6 Molecular Formula
- C15H10O4 (isomer)
- 1.7 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
- 1.8 InChkey
- COCYGNDCWFKTMF-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O
- 1.10 Isomers Smiles
- C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O
2. Properties
- 2.1 Density
- 1.443
- 2.1 Melting point
- 243-246°C
- 2.1 Boiling point
- 494.4°C at 760 mmHg
- 2.1 Refractive index
- 1.698
- 2.1 Flash Point
- 193.5°C
- 2.1 Precise Quality
- 254.05800
- 2.1 PSA
- 70.67000
- 2.1 logP
- 2.87120
- 2.1 Solubility
- DMSO: soluble24mg/mL
- 2.2 Appearance
- Yellow Powder
- 2.3 Storage
- Ambient temperatures.
- 2.4 Chemical Properties
- Yellow Solid
- 2.5 Color/Form
- Yellow powder
- 2.6 pKa
- 6.86±0.40(Predicted)
- 2.7 Water Solubility
- DMSO: soluble 24mg/mL
3. Use and Manufacturing
- 3.1 Usage
- 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.
4. Safety and Handling
- 4.1 Hazard Codes
- Xn
- 4.1 Risk Statements
- 22
- 4.1 Safety Statements
- 24/25
- 4.1 Hazard Declaration
- H302
- 4.1 Caution Statement
- P264, P270, P301+P312, P330, P501
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- DJ3004000
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
38183-03-8Total: 16 Synthesis Route
8. Other Information
- 8.0 Collision Cross Section
- 152 ?2 [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
- 8.1 Mesh Entry Terms
- 6,7-dihydroxyflavone
- 8.2 Chemical Properties
- Yellow Solid
- 8.3 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 Alzheim er's disease. 7,8-Dihydroxyflavone may also provide a therapeutic option in the treatment of other neorological disorders such as Rett syndrome and PTSD.
- 8.4 Uses
- vascular protectant, antihaemorrhagic, tyr kinase B agonist
- 8.5 Biological Activity
- Tyrosine kinase receptor B (TrkB) agonist that binds to the extracellular domain of the receptor (K d = 320 nM). Inhibits glutamate-triggered apoptosis in hippocampal neurons in vitro and in vivo .
9. Computational chemical data
- Molecular Weight: 254.2375g/mol
- Molecular Formula: C15H10O4
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 254.05790880
- Monoisotopic Mass: 254.05790880
- Complexity: 384
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 66.8
- Heavy Atom Count: 19
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwYIAAAAAAAACBQAAAGgAACAAADASAmAAwBoAABgCIAqBSAAACCAAkIAAIiAEGiMgNJzaGNRqCeWOl4BULuYeK7LzOIAABCAAIQABAAAIQABCAAAAAAAAAAA==
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