7,8-dihydroxyflavone

7,8-dihydroxy-2-phenyl-4-benzopyrone

CAS: 38183-03-8 C15 H10 O4 MW: 254.24150000

Identification

Name7,8-dihydroxyflavone
IUPAC7,8-dihydroxy-2-phenylchromen-4-one
CAS Number38183-03-8
EINECS253-812-4
FDA UNIIADB6MA8ZV2
Molecular FormulaC15 H10 O4
Molecular Weight254.24150000
MDL NumberMFCD00006836
Nikkaji NumberJ294.607F
Beilstein0234350
XlogP33.30 (est)

Regulatory

JECFA Food Flavoring2259 7,8-dihydroxyflavone
FEMA Number4830
FDANo 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 SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavoring agents
Recommendation for 7,8-dihydroxyflavone usage levels up tonot for fragrance use.
baked goods-
beverages(nonalcoholic)5.00000
beverages(alcoholic)5.00000
breakfast cereal-
cheese-
chewing gum100.00000
condiments / relishes10.00000
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices5.00000
gelatins / puddings-
granulated sugar-
gravies10.00000
hard candy50.00000
imitation dairy-
instant coffee / tea5.00000
jams / jellies-
meat products10.00000
milk products-
nut products-
other grains-
poultry10.00000
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors30.00000
snack foods50.00000
soft candy50.00000
soups10.00000
sugar substitutes-
sweet sauces-

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Potential Uses

None Found

Natural Occurrence

not found in nature

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.