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Dieckol

Cat No.:V46632 Purity: ≥98%
Dieckol is a naturally occurring phlorotannin found in some brown algae species.
Dieckol
Dieckol Chemical Structure CAS No.: 88095-77-6
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
10mg
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Product Description
Dieckol is a naturally occurring phlorotannin found in some brown algae species. Dieckol has antibacterial, anticancer, antioxidant, antiaging, antidiabetic, and neuro-protective (neuro-protection) effects.
Dieckol (CAS 88095-77-6) is a naturally occurring phlorotannin, a type of polyphenol found in brown seaweeds such as Ecklonia cava. It has a molecular formula of C36H22O18 and a molecular weight of 742.55. Dieckol exhibits a wide range of biological activities including antibacterial, anticancer, antioxidant, anti-aging, anti-diabetic, neuroprotective, antithrombotic, and profibrinolytic actions. It also has effects on hair growth and can improve acute hearing loss.
Biological Activity I Assay Protocols (From Reference)
Targets
Dieckol targets multiple signaling pathways. It inhibits signaling molecules including PI3K, AKT, mTOR, and FAK, which are critical in inducing apoptosis. It also inhibits α-glucosidase and α-amylase in vitro, contributing to its anti-diabetic effects. The compound's antioxidant activity is attributed to its polyphenolic structure, which scavenges free radicals and reduces oxidative stress. Its antibacterial effects are likely due to disruption of bacterial cell membranes or inhibition of bacterial enzymes.
ln Vitro
Dieckol inhibits the signaling molecules PI3K, AKT, mTOR, and FAK, which is critical in inducing apoptosis [1].
In vitro, Dieckol inhibits the signaling molecules PI3K, AKT, mTOR, and FAK, which is critical in inducing apoptosis. It inhibits α-glucosidase and α-amylase activities. The compound shows antibacterial activity against various pathogens, anticancer activity against cancer cell lines, and antioxidant activity through free radical scavenging. It has been shown to inhibit cell proliferation through cell cycle arrest in Hs680.Tr human tracheal fibroblasts. Dieckol also exhibits neuroprotective effects.
ln Vivo
In animal models where a high-fat diet is induced, dieckol significantly inhibits lipid accumulation [1].
In vivo, Dieckol alleviates postprandial hyperglycemia in streptozotocin-induced diabetic mice, demonstrating anti-diabetic effects. The compound shows antithrombotic and profibrinolytic activities. It has been studied for its effects on hair growth. Dieckol has potential applications in diabetes, thrombosis, and other metabolic and cardiovascular disorders. However, detailed in vivo efficacy data and dosing regimens are not extensively reported.
Enzyme Assay
In vitro enzyme/receptor binding assays for Dieckol typically involve enzyme inhibition assays for α-glucosidase and α-amylase. The compound (0.1-1000 μg/mL) is incubated with the enzyme and substrate (e.g., p-nitrophenyl-α-D-glucopyranoside for α-glucosidase) at 37°C for 15-30 minutes. The reaction is stopped, and absorbance is measured at 405 nm. IC50 values are determined from dose-response curves. For antioxidant activity, DPPH or ABTS radical scavenging assays are used. For apoptosis studies, PI3K/AKT/mTOR pathway inhibition is assessed by Western blotting.
Cell Assay
In vitro cellular assays for Dieckol use various cancer cell lines and normal cells. Cells are cultured in appropriate media and treated with various concentrations of the compound (typically 1-100 μg/mL) for 24-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays. Apoptosis is assessed by Annexin V/PI staining and caspase-3/7 activity assays. PI3K/AKT/mTOR pathway proteins are analyzed by Western blotting. Antibacterial activity is assessed by broth microdilution methods to determine MIC values.
Animal Protocol
In vivo animal studies with Dieckol use mouse models of diabetes and thrombosis. In streptozotocin-induced diabetic mice, the compound is administered orally at doses of 10-50 mg/kg, and postprandial blood glucose levels are measured. In thrombosis models, the compound is administered intravenously or orally, and thrombus formation is assessed. Hair growth effects are evaluated in mouse models by measuring hair length and density. However, specific protocols are not extensively detailed.
ADME/Pharmacokinetics
Pharmacokinetic properties of Dieckol are not extensively reported. As a polyphenolic compound with a molecular weight of 742.55, it is expected to have low oral bioavailability due to poor absorption and extensive metabolism. The compound is likely metabolized by gut microbiota and hepatic enzymes. Specific PK parameters such as half-life, Cmax, and AUC are not detailed. The compound is typically administered orally or intraperitoneally in research studies.
Toxicity/Toxicokinetics
The toxicity profile of Dieckol is not extensively reported. As a naturally occurring polyphenol, it is expected to have low toxicity at moderate doses. The compound is for research use only and not for human therapeutic use. Standard toxicity studies would include acute and subchronic toxicity in rodents, cytotoxicity assays in normal cell lines, and assessment of organ function. No specific genotoxicity data are reported.
References

[1]. Dieckol: a brown algal phlorotannin with biological potential. Biomed Pharmacother. 2021 Oct;142:111988.

Additional Infomation
Dihydroxybenzoic acid (Dieckol) is a phloroglucinol compound isolated from the brown algae Ecklonia cava, possessing antioxidant, hepatoprotective, and anticoagulant activities. It functions as a metabolite, free radical scavenger, EC 3.2.1.20 (α-glucosidase) inhibitor, hepatoprotective agent, and anticoagulant. It is a phloroglucinol compound belonging to the aromatic ether and oxoheterocyclic compounds. Its functions are similar to those of phloroglucinol. Dihydroxybenzoic acid has been reported to exist in Eisenia bicyclis and Ecklonia cava, with relevant data available.
Dieckol (CAS 88095-77-6) is a naturally occurring phlorotannin from brown seaweeds with a wide range of biological activities including antibacterial, anticancer, antioxidant, anti-diabetic, neuroprotective, and antithrombotic effects. It has a molecular formula of C36H22O18 and a molecular weight of 742.55. The compound inhibits PI3K/AKT/mTOR/FAK signaling and shows potential in diabetes, thrombosis, and cancer research. It is available for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C36H22O18
Molecular Weight
742.54908
Exact Mass
742.081
CAS #
88095-77-6
PubChem CID
3008868
Appearance
Off-white to light brown solid powder
LogP
7.621
Hydrogen Bond Donor Count
11
Hydrogen Bond Acceptor Count
18
Rotatable Bond Count
6
Heavy Atom Count
54
Complexity
1240
Defined Atom Stereocenter Count
0
SMILES
OC1C=C(OC2C3=C(OC4C(O3)=C(O)C=C(OC3C(O)=CC(OC5C6=C(OC7C(O6)=C(O)C=C(O)C=7)C(O)=CC=5O)=CC=3O)C=4)C(O)=CC=2O)C=C(O)C=1
InChi Key
DRZQFGYIIYNNEC-UHFFFAOYSA-N
InChi Code
InChI=1S/C36H22O18/c37-12-1-13(38)3-15(2-12)49-31-22(44)10-25(47)34-35(31)54-30-21(43)8-17(9-27(30)52-34)48-28-19(41)6-16(7-20(28)42)50-32-23(45)11-24(46)33-36(32)53-29-18(40)4-14(39)5-26(29)51-33/h1-11,37-47H
Chemical Name
4-[4-[6-(3,5-dihydroxyphenoxy)-4,7,9-trihydroxydibenzo-p-dioxin-2-yl]oxy-3,5-dihydroxyphenoxy]dibenzo-p-dioxin-1,3,6,8-tetrol
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

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 : ~50 mg/mL (~67.34 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.37 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.3467 mL 6.7336 mL 13.4671 mL
5 mM 0.2693 mL 1.3467 mL 2.6934 mL
10 mM 0.1347 mL 0.6734 mL 1.3467 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.

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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)
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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.

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