7,8-dihydroxyflavone
7,8-dihydroxy-2-phenyl-4-benzopyrone
Identification
| Name | 7,8-dihydroxyflavone |
| IUPAC | 7,8-dihydroxy-2-phenylchromen-4-one |
| CAS Number | 38183-03-8 |
| EINECS | 253-812-4 |
| FDA UNII | ADB6MA8ZV2 |
| Molecular Formula | C15 H10 O4 |
| Molecular Weight | 254.24150000 |
| MDL Number | MFCD00006836 |
| Nikkaji Number | J294.607F |
| Beilstein | 0234350 |
| XlogP3 | 3.30 (est) |
Regulatory
| JECFA Food Flavoring | 2259 7,8-dihydroxyflavone |
| FEMA Number | 4830 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
Physical Properties
| Appearance | pale yellow powder (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 494.40 °C. @ 760.00 mm Hg (est) |
| Flash Point | 380.00 °F. TCC ( 193.50 °C. ) (est) |
| logP (o/w) | 2.760 (est) |
| Soluble in | water, 149.5 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for 7,8-dihydroxyflavone usage levels up to | not for fragrance use. |
| baked goods | - |
| beverages(nonalcoholic) | 5.00000 |
| beverages(alcoholic) | 5.00000 |
| breakfast cereal | - |
| cheese | - |
| chewing gum | 100.00000 |
| condiments / relishes | 10.00000 |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | - |
| fruit ices | 5.00000 |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | 10.00000 |
| hard candy | 50.00000 |
| imitation dairy | - |
| instant coffee / tea | 5.00000 |
| jams / jellies | - |
| meat products | 10.00000 |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | 10.00000 |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | 30.00000 |
| snack foods | 50.00000 |
| soft candy | 50.00000 |
| soups | 10.00000 |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 7,8-dihydroxy-2-phenyl-
7,8-
dihydroxy-2-phenyl-4-benzopyrone
7,8-
dihydroxy-2-phenyl-4H-1-benzopyran-4-one
7,8-
dihydroxy-2-phenyl-4H-chromen-4-one
7,8-
dihydroxy-2-phenyl-chromen-4-one
7,8-
dihydroxy-2-phenylchromen-4-one
7,8-
dihydroxy-flavone
PubMed:
7, 8-Dihydroxyflavone induces synapse expression of AMPA GluA1 and ameliorates cognitive and spine abnormalities in a mouse model of fragile X syndrome.
PubMed:
Biochemical and biophysical investigation of the brain-derived neurotrophic factor mimetic 7,8-dihydroxyflavone in the binding and activation of the TrkB receptor.
PubMed:
7,8-dihydroxyflavone protects PC12 cells against 6-hydroxydopamine-induced cell death through modulating PI3K/Akt and JNK pathways.
PubMed:
Behavior of the potential antitumor V(IV)O complexes formed by flavonoid ligands. 1. Coordination modes and geometry in solution and at the physiological pH.
PubMed:
Methylation and subsequent glycosylation of 7,8-dihydroxyflavone.
PubMed:
Infralimbic BDNF/TrkB enhancement of GluN2B currents facilitates extinction of a cocaine-conditioned place preference.
PubMed:
Small-molecule TrkB agonist 7,8-dihydroxyflavone reverses cognitive and synaptic plasticity deficits in a rat model of schizophrenia.
PubMed:
7,8-Dihydroxyflavone improves motor performance and enhances lower motor neuronal survival in a mouse model of amyotrophic lateral sclerosis.
PubMed:
7,8-Dihydroxyflavone, a small molecule TrkB agonist, improves spatial memory and increases thin spine density in a mouse model of Alzheimer disease-like neuronal loss.
PubMed:
Effect of 7, 8-dihydroxyflavone on the up-regulation of Nrf2-mediated heme oxygenase-1 expression in hamster lung fibroblasts.
PubMed:
7,8-Dihydroxyflavone attenuates the release of pro-inflammatory mediators and cytokines in lipopolysaccharide-stimulated BV2 microglial cells through the suppression of the NF-κB and MAPK signaling pathways.
PubMed:
7,8-Dihydroxyflavone protects human keratinocytes against oxidative stress-induced cell damage via the ERK and PI3K/Akt-mediated Nrf2/HO-1 signaling pathways.
PubMed:
Brain-derived neurotrophic factor enhances cholinergic contraction of longitudinal muscle of rabbit intestine via activation of phospholipase C.
PubMed:
Coupling energy homeostasis with a mechanism to support plasticity in brain trauma.
PubMed:
7,8-dihydroxyflavone ameliorates scopolamine-induced Alzheimer-like pathologic dysfunction.
PubMed:
Vasorelaxing and antihypertensive effects of 7,8-dihydroxyflavone.
PubMed:
Antioxidant action of 7,8-dihydroxyflavone protects PC12 cells against 6-hydroxydopamine-induced cytotoxicity.
PubMed:
Towards tropomyosin-related kinase B (TrkB) receptor ligands for brain imaging with PET: radiosynthesis and evaluation of 2-(4-[(18)F]fluorophenyl)-7,8-dihydroxy-4H-chromen-4-one and 2-(4-([N-methyl-(11)C]-dimethylamino)phenyl)-7,8-dihydroxy-4H-chromen-4-one.
PubMed:
7,8-Dihydroxyflavone suppresses oxidative stress-induced base modification in DNA via induction of the repair enzyme 8-oxoguanine DNA glycosylase-1.
PubMed:
Disruption of the expression of the proprotein convertase PC7 reduces BDNF production and affects learning and memory in mice.
PubMed:
7,8-Dihydroxyflavone improves memory consolidation processes in rats and mice.
PubMed:
7,8-dihydroxyflavone, a small-molecule tropomyosin-related kinase B (TrkB) agonist, attenuates cerebral ischemia and reperfusion injury in rats.
PubMed:
Small-molecule trkB agonists promote axon regeneration in cut peripheral nerves.
PubMed:
7,8-dihydroxyflavone prevents synaptic loss and memory deficits in a mouse model of Alzheimer's disease.
PubMed:
7,8-Dihydroxyflavone, a TrkB agonist, attenuates behavioral abnormalities and neurotoxicity in mice after administration of methamphetamine.
PubMed:
Protection of spiral ganglion neurons from degeneration using small-molecule TrkB receptor agonists.
PubMed:
Small molecules activating TrkB receptor for treating a variety of CNS disorders.
PubMed:
Individual differences in novelty seeking predict subsequent vulnerability to social defeat through a differential epigenetic regulation of brain-derived neurotrophic factor expression.
PubMed:
Effect of 7,8-dihydroxyflavone as an antioxidant on in vitro maturation of oocytes and development of parthenogenetic embryos in pigs.
PubMed:
Thyroxin treatment protects against white matter injury in the immature brain via brain-derived neurotrophic factor.
PubMed:
Probing the ability of presynaptic tyrosine kinase receptors to regulate striatal dopamine dynamics.
PubMed:
Activation of BDNF signaling prevents the return of fear in female mice.
PubMed:
Effects of TrkB agonist 7,8-dihydroxyflavone on sensory gating deficits in mice after administration of methamphetamine.
PubMed:
Modulatory effects of the novel TrkB receptor agonist 7,8-dihydroxyflavone on synaptic transmission and intrinsic neuronal excitability in mouse visual cortex in vitro.
PubMed:
7,8-Dihydroxyflavone leads to survival of cultured embryonic motoneurons by activating intracellular signaling pathways.
PubMed:
TrkB receptor agonist 7, 8 dihydroxyflavone triggers profound gender- dependent neuroprotection in mice after perinatal hypoxia and ischemia.
PubMed:
Small-molecule TrkB receptor agonists improve motor function and extend survival in a mouse model of Huntington's disease.
PubMed:
O-methylated metabolite of 7,8-dihydroxyflavone activates TrkB receptor and displays antidepressant activity.
PubMed:
Apoptosis induction of human leukemia U937 cells by 7,8-dihydroxyflavone hydrate through modulation of the Bcl-2 family of proteins and the MAPKs signaling pathway.
PubMed:
Prelimbic BDNF and TrkB signaling regulates consolidation of both appetitive and aversive emotional learning.
PubMed:
Influence of glucose on the human serum albumin-flavone interaction and their antioxidant activity.
PubMed:
Protective effects of 7,8-dihydroxyflavone on retinal ganglion and RGC-5 cells against excitotoxic and oxidative stress.
PubMed:
Optimization of a small tropomyosin-related kinase B (TrkB) agonist 7,8-dihydroxyflavone active in mouse models of depression.
PubMed:
Companions reverse stressor-induced decreases in neurogenesis and cocaine conditioning possibly by restoring BDNF and NGF levels in dentate gyrus.
PubMed:
Activation of TrkB by 7,8-dihydroxyflavone prevents fear memory defects and facilitates amygdalar synaptic plasticity in aging.
PubMed:
7,8-dihydroxyflavone rescues spatial memory and synaptic plasticity in cognitively impaired aged rats.
PubMed:
7,8-dihydroxyflavone induces G1 arrest of the cell cycle in U937 human monocytic leukemia cells via induction of the Cdk inhibitor p27 and downregulation of pRB phosphorylation.
PubMed:
Fear extinction and BDNF: translating animal models of PTSD to the clinic.
PubMed:
7,8-Dihydroxyflavone exhibits anti-inflammatory properties by downregulating the NF-κB and MAPK signaling pathways in lipopolysaccharide-treated RAW264.7 cells.
PubMed:
The novel TrkB receptor agonist 7,8-dihydroxyflavone enhances neuromuscular transmission.
PubMed:
7,8-dihydroxyflavone exhibits therapeutic efficacy in a mouse model of Rett syndrome.
PubMed:
Epigenetic enhancement of BDNF signaling rescues synaptic plasticity in aging.
PubMed:
Kaempferol inhibits enterovirus 71 replication and internal ribosome entry site (IRES) activity through FUBP and HNRP proteins.
PubMed:
7,8-dihydroxyflavone, a small-molecule TrkB agonist, reverses memory deficits and BACE1 elevation in a mouse model of Alzheimer's disease.
PubMed:
Vulnerability to depression: from brain neuroplasticity to identification of biomarkers.
PubMed:
Structure of flavonoids influences the degree inhibition of Benzo(a)pyrene - induced DNA damage and micronuclei in HepG2 cells.
PubMed:
Antioxidant activity of 7,8-dihydroxyflavone provides neuroprotection against glutamate-induced toxicity.
PubMed:
7,8-dihydroxyflavone, a TrkB receptor agonist, blocks long-term spatial memory impairment caused by immobilization stress in rats.
PubMed:
Effect of 7,8-dihydroxyflavone, a small-molecule TrkB agonist, on emotional learning.
PubMed:
A synthetic 7,8-dihydroxyflavone derivative promotes neurogenesis and exhibits potent antidepressant effect.
PubMed:
Characterization of an O-methyltransferase from Streptomyces avermitilis MA-4680.
PubMed:
[Effect of seven kinds of flavonoids on recombinant human protein tyrosine phosphatase].
PubMed:
A selective TrkB agonist with potent neurotrophic activities by 7,8-dihydroxyflavone.
PubMed:
Prelimbic cortical BDNF is required for memory of learned fear but not extinction or innate fear.
PubMed:
Acidity of hydroxyl groups: an overlooked influence on antiradical properties of flavonoids.
PubMed:
Preventive effect of 7,8-dihydroxyflavone against oxidative stress induced genotoxicity.
PubMed:
Empirically predicted 13C NMR chemical shifts for 8-hydroxyflavone starting from 7,8,4'-trihydroxyflavone and from 7,8-dihydroxyflavone.
PubMed:
Antitrypanosomal and antileishmanial activities of flavonoids and their analogues: in vitro, in vivo, structure-activity relationship, and quantitative structure-activity relationship studies.
PubMed:
Human NAD(P)H:quinone oxidoreductase inhibition by flavonoids in living cells.
PubMed:
Flavonoids: structural requirements for antiproliferative activity on breast cancer cells.
PubMed:
Different catalytic properties and inhibitor responses of the goldfish brain and ovary aromatase isozymes.
PubMed:
Reactivities of flavonoids with different hydroxyl substituents for the cleavage of DNA in the presence of Cu(II).
PubMed:
Molecular characterization of binding of substrates and inhibitors to DT-diaphorase: combined approach involving site-directed mutagenesis, inhibitor-binding analysis, and computer modeling.
PubMed:
Estrogenic and antiproliferative activities on MCF-7 human breast cancer cells by flavonoids.
PubMed:
Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study.
PubMed:
Binding characteristics of aromatase inhibitors and phytoestrogens to human aromatase.
PubMed:
Inhibition of mitochondrial respiration and cyanide-stimulated generation of reactive oxygen species by selected flavonoids.
PubMed:
Effects of phenolic compounds on bromobenzene-mediated hepatotoxicity in mice.
PubMed:
Effect of various flavonoids on lysosomes subjected to an oxidative or an osmotic stress.
PubMed:
Synthesis of new annellated flavonoid derivatives possessing spasmolytic activity--VII.