7,8-Dihydroxyflavone

HCID 1880CAS 38183-03-8
Substructure searchFind similar structures

Basic information

Standard SMILES
O=c1cc(-c2ccccc2)oc2c(O)c(O)ccc12
InChIKey
COCYGNDCWFKTMF-UHFFFAOYSA-N
Molecular formula
C15H10O4
Average molar mass
254.24 g/mol
Monoisotopic mass
254.0579088

Overview

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 tropomyosin-related kinase B receptor agonist, an antioxidant, an antidepressant, an antineoplastic agent and a plant metabolite.

Names & identifiers

Preferred name
7,8-Dihydroxyflavone
IUPAC
7,8-dihydroxy-2-phenylchromen-4-one
English name
7,8-Dihydroxyflavone
Molecular formula
C15H10O4
Molecular weight
254.24

Names & synonyms

7,8-dihydroxyflavone38183-03-87,8-dihydroxy-2-phenyl-4H-chromen-4-one7,8-DHF4H-1-Benzopyran-4-one, 7,8-dihydroxy-2-phenyl-7,8-dihydroxy-2-phenylchromen-4-one7,8-Dihydroxy-flavone7,8-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one7,8-Dihydroxy-2-phenyl-4-benzopyroneADB6MA8ZV2NSC-750341FEMA NO. 4830
Show more names
7,8-dihydroxyflavone (7,8-DHF)7,8-DIHYDROXY7,8-Di-OH flavone8-DihydroxyflavoneTIMTEC-BB SBB000930DIHYDROXYFLAVONE, 7,8-
CHEBI:140464DTXSID00191568RefChem:105589DTXCID40114059253-812-47,8-Dihydroxyflavone hydrate7,8-Dihydroxy-2-phenyl-chromen-4-oneMFCD00006836

Database identifiers

CAS
38183-03-8
PubChem CID
1880
DTXSID
DTXSID00191568
ChEMBL
CHEMBL75267
ChEBI
CHEBI:140464
UNII
ADB6MA8ZV2
EC Number
253-812-4
Nikkaji
J294.607F

Properties

Computed structural properties

XLogP
3.3
Topological polar surface area
66.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
19

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Solubility · 2 items

Very slightly soluble

Very slightly soluble (in ethanol)

Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionPale yellow powder; Bland aroma
Collision Cross Section · 2 items

173.79 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

152 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
243 · 243-246°C
Boiling point
494.4 · 494.4±45.0 °C(Predicted)
Density
1.443 · 1.443±0.06 g/cm3(Predicted)
FEMA
4830 · 4830 | 7,8-DIHYDROXYFLAVONE
storage temp.
Inert atmosphere,Room Temperature
solubility
24 mg/mL · DMSO: soluble24mg/mL

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk
3
rtecs
DJ3004000
hs_code
2932990090
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Uses & manufacturing

Use Classification · 2 items

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Applications · 2 items

Description7,8-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.

Uses7,8-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.

Upstream & downstream products

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海达立康医药科技有限公司18658316824
济南百隆化学有限公司[email protected] · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

1 records
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