7,8-Dihydroxyflavone Hydrate - ≥98%(HPLC) , CAS No.38183-03-8

CAS: 38183-03-8 Cat. No.: D137213 Molecular Weight: 254.24 (anhydrous basis) EC Number: 253-812-4

GRADE & PURITY ≥98%(HPLC)

Synonyms

NINDS_000371 | 7,8-dihydroxy-2-phenylchromen-4-one | MFCD00006836 | 7,8-Dihydroxy-2-phenyl-4-benzopyrone | 4H-1-Benzopyran-4-one, 7,8-dihydroxy-2-phenyl- | HMS3886D10 | KBio2_006703 | 5-18-04-00079 (Beilstein Handbook Reference) | BRD-K49535716-001-03-2 |

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

7,8-Dihydroxyflavone hydrate is a tyrosine kinase receptor B (TrkB) agonist that binds to the extracellular domain of the receptor with a Kd value of 320 nM. It also inhibits glutamate-triggered apoptosis in hippocampal neurons in vitro.
7,8-Dihydroxyflavone (7,8-DHF), a selective tyrosine kinase receptor B (neurotrophic factor/tropomyosin-receptor-kinase B; TrkB) agonist, may be used to help identify and differentiate the physiological effects and cell signaling pathways mediated by TrkB activation, such as those involving neuroprotection, memory, vasorelaxation and hypertension. 7,8-Dihydroxyflavone may be used to study its effects on scopolamine induced Alzheimer-like pathologic dysfunction.

Specifications

Synonyms

NINDS_000371 | 7, 8-dihydroxy-2-phenylchromen-4-one | MFCD00006836 | 7, 8-Dihydroxy-2-phenyl-4-benzopyrone | 4H-1-Benzopyran-4-one, 7, 8-dihydroxy-2-phenyl- | HMS3886D10 | KBio2_006703 | 5-18-04-00079 (Beilstein Handbook Reference) | BRD-K49535716-001-03-2 |

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

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

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504750515
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750515
• Canonical Smiles: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O
• IUPAC Name: 7,8-dihydroxy-2-phenylchromen-4-one
• InChIKey: COCYGNDCWFKTMF-UHFFFAOYSA-N
• 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
• Isomeric SMILES: C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C=C3)O)O
• RTECS: DJ3004000
• Molecular Weight: 254.24 (anhydrous basis)
• Reaxy-Rn: 234350
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=234350&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Flavones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Flavones
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavones
• Alternative Parents: 8-hydroxyflavonoids 7-hydroxyflavonoids Chromones Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Heteroaromatic compounds Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 7-hydroxyflavonoid - 8-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Chromone - Benzopyran - 1-benzopyran - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Pyranone - Monocyclic benzene moiety - Benzenoid - Pyran - Heteroaromatic compound - Organoheterocyclic compound - Oxacycle - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ALDH2 Tclin Aldehyde dehydrogenase (509 Activities)

Discover Target: ALDH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

VDR Tclin Vitamin D receptor (26531 Activities)

Discover Target: VDR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BAD Tchem Bcl2-antagonist of cell death (BAD) (147 Activities)

Discover Target: BAD

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)

Discover Target: LCK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

IKBKB Tchem Inhibitor of nuclear factor kappa B kinase beta subunit (5554 Activities)

Discover Target: IKBKB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)

Discover Target: ALOX15B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PLCG1 Tchem Phospholipase C-gamma-1 (184 Activities)

Discover Target: PLCG1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TOP2B Tclin DNA topoisomerase II beta (959 Activities)

Discover Target: TOP2B

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

Discover Target: ALOX15

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TERT Tchem Telomerase reverse transcriptase (2428 Activities)

Discover Target: TERT

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

Discover Target: TP53

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MCF7 (126967 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SH-SY5Y (11521 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

U-251 (51189 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A549 (127892 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

H9 (1832 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK293 (82097 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NTRK2 Tclin Neurotrophic tyrosine kinase receptor type 2 (3279 Activities)

Discover Target: NTRK2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

Discover Target: HSD17B10

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

POLK Tbio DNA polymerase kappa (8653 Activities)

Discover Target: POLK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

Discover Target: KDM4E

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SMN1 Tchem Survival motor neuron protein (34246 Activities)

Discover Target: SMN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

Discover Target: HPGD

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

Discover Target: USP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

Discover Target: MEN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Mapk1 MAP kinase ERK2 (650 Activities)

Discover Target: Mapk1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Salmonella typhimurium (15756 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus epidermidis (22802 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Human immunodeficiency virus 1 (70413 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma brucei rhodesiense (7991 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Stenotrophomonas maltophilia (1743 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

N2a (708 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Syrian golden hamster (1610 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

lasR Transcriptional activator protein lasR (432 Activities)

Discover Target: lasR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mapt Microtubule-associated protein tau (6 Activities)

Discover Target: Mapt

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

Discover Target: fba

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Impa1 Inositol monophosphatase 1 (16203 Activities)

Discover Target: Impa1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Ntrk2 BDNF/NT-3 growth factors receptor (124 Activities)

Discover Target: Ntrk2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

gyrB DNA gyrase (2092 Activities)

Discover Target: gyrB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Maob Monoamine oxidase (439 Activities)

Discover Target: Maob

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rhlR Regulatory protein RhlR (305 Activities)

Discover Target: rhlR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (Partly miscible), alkali hydroxide solutions, and DMSO (24 mg/ml).,
• Melt Point(°C): 245 °C
• Molecular Weight: 254.240 g/mol
• XLogP3: 3.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 254.058 Da
• Monoisotopic Mass: 254.058 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 384.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Jialu Luan, Shuhui Zhang, Yixin Xu, Liang Wen, Xizeng Feng.  (2023)  Effects of microplastic exposure on the early developmental period and circadian rhythm of zebrafish (Danio rerio): A comparative study of polylactic acid and polyglycolic acid.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:37167737] [10.1016/j.ecoenv.2023.114994]

2. Peng-Zhou Hang, Feng-Qin Ge, Man-Ru Zhang, Qi-Hang Li, Hua-Qing Yu, Yu-Chen Song, Dan-Dan Guo, Jing Zhao, Hua Zhu.  (2023)  BDNF mimetic 7,8-dihydroxyflavone rescues rotenone-induced cytotoxicity in cardiomyocytes by ameliorating mitochondrial dysfunction.  FREE RADICAL BIOLOGY AND MEDICINE,      [PMID:36764626] [10.1016/j.freeradbiomed.2023.02.006]

3. Zhao Jing, Li Peifeng, Zhu Hua, Ge Fengqin, Liu Jie, Xia Jingjun, Hang Pengzhou.  (2021)  7,8-Dihydroxyflavone suppresses proliferation and induces apoptosis of human osteosarcoma cells.  ACTA BIOCHIMICA ET BIOPHYSICA SINICA,  53  (7): (903-911).  [PMID:34019097] [10.1093/abbs/gmab060]

4. Li-Feng Li, Meng-Di Wang, Chen-Yang Zhang, Meng-Yao Jin, Hua-Lei Chen, Huan Luo, Tian-Yu Hou, Zhi-Jun Zhang, He Li.  (2025)  Influence of hydroxyl substitution on the inhibition of flavonoids in advanced glycation end-products formation in glucose-lysine-arginine Maillard reaction models.  FOOD RESEARCH INTERNATIONAL,      [PMID:40086959] [10.1016/j.foodres.2025.116068]

5. Haolin Zhang, Jingjing Zhang, Hui Cao, Petra Högger, Randolph Arroo, Mohamed A. Farag, Avi Shpigelman, Jianbo Xiao, Chunlin Li.  (2025)  Amination of Flavonoids Possessing a Pyrogallol Group in Cell Culture Medium at 37°C.  Food Frontiers,  6  (2): (1058-1078).  [PMID:] [10.1002/fft2.70002]