7,8-Dihydroxyflavone

Names

[ Name ]:
7,8-Dihydroxyflavone

[Synonym ]:
7,8-dihydroxy-2-phenylchromen-4-one
7,8-Dihydroxyflavone Hydrate
7,8-Dihydroxy-2-phenyl-4H-chromen-4-one
EINECS 253-812-4
7,8-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one
MFCD00006836
7,8-Dihydroxyflavone
4H-1-Benzopyran-4-one, 7,8-dihydroxy-2-phenyl-

Biological Activity

[Description]:

7,8-Dihydroxyflavone is a potent and selective TrkB agonist that mimics the physiological actions of Brain-derived neurotrophic factor (BDNF). Displays therapeutic efficacy toward various neurological diseases[1].

[Related Catalog]:

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> Trk Receptor

Research Areas >> Neurological Disease

[Target]

TrkB[1]

[In Vitro]

7,8-Dihydroxyflavone (500 nM) protects the primary cortical neurons and locus coeruleus (LC) neurons from Aβ-induced toxicity and promotes dendritic growth and synaptogenesis[1].

[In Vivo]

7,8-Dihydroxyflavone (5 mg/kg/day) prevents synaptic loss and memory deficits in a mouse model of Alzheimer’s Disease[1]. Administration of 7,8- dihydroxyflavone to mice activates TrkB in the brain, inhibits kainic acid-induced toxicity, decreases infarct volumes in stroke in a TrkBdependent manner, and is neuroprotective in an animal model of Parkinson disease[2].

[References]

[1]. Zhang Z, et al. 7,8-dihydroxyflavone prevents synaptic loss and memory deficits in a mouse model of Alzheimer's disease. Neuropsychopharmacology. 2014 Feb;39(3):638-50.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
494.4±45.0 °C at 760 mmHg

[ Melting Point ]:
243-246°C

[ Molecular Formula ]:
C₁₅H₁₀O₄

[ Molecular Weight ]:
254.24

[ Flash Point ]:
193.5±22.2 °C

[ Exact Mass ]:
254.057907

[ PSA ]:
70.67000

[ LogP ]:
2.51

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.699

[ Storage condition ]:
Store at +4°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ3004000

CHEMICAL NAME :: 4H-1-Benzopyran-4-one, 7,8-dihydroxy-2-phenyl-

CAS REGISTRY NUMBER :: 38183-03-8

BEILSTEIN REFERENCE NO. :: 0234350

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C15-H10-O4

MOLECULAR WEIGHT :: 254.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Human HeLa cell

DOSE/DURATION :: 12500 ug/L

REFERENCE :: PYTCAS Phytochemistry. An International Journal of Plant Biochemistry. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1961- Volume(issue)/page/year: 27,1017,1988

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ Safety Phrases ]:
S24/25

[ RTECS ]:
DJ3004000

[ HS Code ]:
2914400090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914400090

[ Summary ]:
2914400090 other ketone-alcohols and ketone-aldehydes。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%