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7,8-Dihydroxyflavone

Alias: DHF 7,8-DHF 7,8-Dihydroxyflavone
Cat No.:V9113 Purity: ≥98%
7,8-Dihydroxyflavone is a potent and specific TrkB agonist that mimics the physiological effects of brain-derived neurotrophic factor (BDNF).
7,8-Dihydroxyflavone
7,8-Dihydroxyflavone Chemical Structure CAS No.: 38183-03-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
50mg
100mg
250mg
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Product Description
7,8-Dihydroxyflavone is a potent and specific TrkB agonist that mimics the physiological effects of brain-derived neurotrophic factor (BDNF). 7,8-Dihydroxyflavone may be used to be utilized in study/research of a variety of neurological diseases.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
7,8-Dihydroxyflavone (500 nM) protects primary cortical neurons and locus coeruleus (LC) neuron shells from Aβ-induced toxicity and stimulates dendritic development and synapse formation [1].
ln Vivo
In Alzheimer's disease models, 7,8-Dihydroxyflavone (5 mg/kg/day) protects synapse loss and memory deficits [1]. Application of 7,8-dihydroxyflavone to the model has neuroprotective benefits in animal models of Parkinson's disease and activates TrkB in the brain center, suppresses toxicity generated by red algae toxin, and lowers infarct volume in stroke in a TrkB-dependent way [2].
References

[1]. 7,8-dihydroxyflavone prevents synaptic loss and memory deficits in a mouse model of Alzheimer's disease. Neuropsychopharmacology. 2014 Feb;39(3):638-50.

Additional Infomation
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.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H10O4
Molecular Weight
254.2375
Exact Mass
254.057
CAS #
38183-03-8
PubChem CID
1880
Appearance
Light yellow to yellow solid powder
Density
1.4±0.1 g/cm3
Boiling Point
494.4±45.0 °C at 760 mmHg
Melting Point
243-246°C
Flash Point
193.5±22.2 °C
Vapour Pressure
0.0±1.3 mmHg at 25°C
Index of Refraction
1.699
LogP
2.51
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
19
Complexity
384
Defined Atom Stereocenter Count
0
SMILES
O1C(=C([H])C(C2C([H])=C([H])C(=C(C1=2)O[H])O[H])=O)C1C([H])=C([H])C([H])=C([H])C=1[H]
InChi Key
COCYGNDCWFKTMF-UHFFFAOYSA-N
InChi Code
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
Chemical Name
7,8-Dihydroxy-2-phenyl-chromen-4-one
Synonyms
DHF 7,8-DHF 7,8-Dihydroxyflavone
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ≥ 100 mg/mL (~393.33 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (9.83 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.9333 mL 19.6665 mL 39.3329 mL
5 mM 0.7867 mL 3.9333 mL 7.8666 mL
10 mM 0.3933 mL 1.9666 mL 3.9333 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • 7,8-dihydroxyflavone (7,8-DHF) prevents Aβ-induced neurotoxicity in cultured cortical neurons and locus coeruleus (LC) neurons. (a) 7,8-DHF protected cortical neurons form Aβ toxicity. Cultured cortical neurons (DIV 12) were exposed to pre-aggregated Aβ (1–42, 20 μM) for 18 h in the presence or absence of 7,8-DHF (500 nM). Neurons were immunostained with neuronal marker MAP2. Neuronal apoptosis was detected by TUNEL staining. The neurons in apoptosis were indicated by white arrows. (b) 7,8-DHF protects LC neurons from Aβ toxicity. LC neurons were exposed to pre-aggregated Aβ (25–35, 20 μM) for 18 h in the presence or absence of 7,8-DHF (500 nM) and the Trk receptor inhibitor K252 (100 nM), and stained with tyrosine hydroxylase (TH) (red), DAPI (blue) and TUNEL (green). The percentage of apoptotic cells was determined by TUNEL staining. (c) Quantification of TUNEL-positive cells show that 7,8-DHF decreased the apoptotic rate of cortical neurons induced by Aβ. Data represent the mean±SEM from three independent experiments. *P<0.01. (d) Quantification of TUNEL-positive neurons shows that 7,8-DHF attenuated Aβ-induced apoptosis in LC neurons. The protective effect of 7,8-DHF was abolished by K252. Data represent the mean±SEM from three independent experiments. *P<0.01.[1].Zhang Z, et al. 7,8-dihydroxyflavone prevents synaptic loss and memory deficits in a mouse model of Alzheimer's disease. Neuropsychopharmacology. 2014 Feb;39(3):638-50.
  • 7,8-dihydroxyflavone (7,8-DHF) promotes synaptogenesis in primary cultured neurons. (a) Representative image of primary cortical neurons. The neurons were cultured in the presence or absence of 7,8-DHF (500 nM) for 3 days and immunostained with antibody to neuronal marker MAP2. (b) Quantification of total dendritic length. 7,8-DHF promoted dendritic elongation in primary neurons. (c) The number of crossings and area under the curve (AUC) following 7,8-DHF treatment.(d) The presynaptic structure of cultured neurons. Vehicle- or 7,8-DHF-treated neurons were double stained with the presynaptic markers VGAT (green) and bassoon (red). The number of synapses (e) and synapse size (f) was quantified. 7,8-DHF significantly promoted the number and size of neurons. Data represent the mean±SEM from three independent experiments. *P<0.01.[1].Zhang Z, et al. 7,8-dihydroxyflavone prevents synaptic loss and memory deficits in a mouse model of Alzheimer's disease. Neuropsychopharmacology. 2014 Feb;39(3):638-50.
  • 7,8-dihydroxyflavone (7,8-DHF) elicits tropomyosin-receptor-kinase B (TrkB) and downstream signaling activation in 5XFAD mice. (a) Immunohistochemistry staining for TrkB and p-TrkB in 5XFAD brain sections. Two months old 5XFAD mice were treated with 7,8-DHF (5 mg/kg/day) or vehicle consecutively for 4 months. The phosphorylation of TrkB in dentate gyrus was detected by immunohistochemistry with anti-TrkB and anti-p-TrkB 816 antibody. Arrows indicate the p-TRKB-positive cells. Scale bar, 50 μm. (b) Quantification of p-TrkB-positive neurons in the dentate gyrus. Note that 7,8-DHF treatment elicited the phosphorylation of TrkB in 5XFAD mice. Data are shown as mean±SEM (n=n=3 mice per group). *P<0.01. (c) Immunoblotting analysis of the phophorylation of TrkB and its downstream signaling pathways Akt and ERK/MAPK. The level of p-TrkB, p-AKT and p-ERK/MAPK was increased by 7,8-DHF treatment, indicating that 7,8-DHF elicits TrkB and its downstream signaling pathways. n=3 mice per group. *P<0.05.[1].Zhang Z, et al. 7,8-dihydroxyflavone prevents synaptic loss and memory deficits in a mouse model of Alzheimer's disease. Neuropsychopharmacology. 2014 Feb;39(3):638-50.
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