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D5446

Sigma-Aldrich

7,8-Dihydroxyflavone hydrate

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C15H10O4 · xH2O
CAS Number:
Molecular Weight:
254.24 (anhydrous basis)
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

storage condition

desiccated

solubility

DMSO: 24 mg/mL

storage temp.

room temp

SMILES string

Oc1ccc2C(=O)C=C(Oc2c1O)c3ccccc3

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

InChI key

COCYGNDCWFKTMF-UHFFFAOYSA-N

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Application

7,8-Dihydroxyflavone hydrate has been used as tropomyosin-receptor-kinase B (TrkB) agonist in mice and to inhibit TrkB for monitoring evoked excitatory postsynaptic currents (eEPSCs).

Biochem/physiol Actions

7,8-Dihydroxyflavone (7,8-DHF) may be used to help identify and differentiate the physiological effects and cell signaling pathways mediated by TrkB activation, such as those involving, memory, vasorelaxation and hypertension. 7,8-DHF elicits protection in scopolamine induced Alzheimer-like pathologic dysfunction.
7,8-Dihydroxyflavone is a selective tyrosine kinase receptor B (TrkB) receptor agonist. It manifests all the therapeutic effects of brain-derived neurotrophic factor (BDNF)—such as protecting neurons from apoptosis, inhibiting kainic acid-induced toxicity, decreasing infarct volumes in stroke, and neuroprotecting in an animal model of Parkinson′s disease—without the poor pharmacokinetic profile of BDNF limiting its therapeutic potential.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Oligodendrocytes regulate presynaptic properties and neurotransmission through BDNF signaling in the mouse brainstem
Jang M, et al.
eLife, 8, e42156-e42156 (2019)
7, 8-dihydroxyflavone ameliorates scopolamine-induced Alzheimer-like pathologic dysfunction
Chen C, et al.
Rejuvenation Research, 17(3), 249-254 (2014)
Autism-like behavior caused by deletion of vaccinia-related kinase 3 is improved by TrkB stimulation
Kang MS, et al.
The Journal of Experimental Medicine, 214(10), 2947-2966 (2017)
Vasorelaxing and antihypertensive effects of 7, 8-dihydroxyflavone
Huai R
American Journal of Hypertension, 27(5), 750-760 (2013)
Maria N Schultz et al.
Learning & memory (Cold Spring Harbor, N.Y.), 27(9), 346-354 (2020-08-21)
Angelman syndrome is a rare neurodevelopmental disorder caused by a mutation in the maternal allele of the gene Ube3a The primary symptoms of Angelman syndrome are severe cognitive deficits, impaired motor functions, and speech disabilities. Analogous phenotypes have been detected

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