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2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside

Cat No.:V29195 Purity: ≥98%
2,3,4',5-tetrahydroxystilbene 2-OD-glucoside is extracted from the roots of Polygonaceae species and inhibits the formation of 5-HETE, HHT and thromboxane B2.
2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside
2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside Chemical Structure CAS No.: 82373-94-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
2,3,4',5-tetrahydroxystilbene 2-OD-glucoside is extracted from the roots of Polygonaceae species and inhibits the formation of 5-HETE, HHT and thromboxane B2.
2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside (CAS 82373-94-2) is a natural flavonoid glycoside and a derivative of stilbene, commonly found in various plants including grapes and Japanese knotweed. It is also known as 2,3,4',5-tetrahydroxystilbene 2-O-D-glucoside. It is extracted from the roots of Polygonaceae species. It inhibits the formation of 5-HETE, HHT, and thromboxane B2. It is a resveratrol analog with glucoside contained in the traditional Chinese herbal medicine Polygonum multiflorum Thunb. It is used in research on inflammation, thrombosis, and oxidative stress.
Biological Activity I Assay Protocols (From Reference)
Targets
2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside targets the arachidonic acid metabolic pathway. It inhibits the formation of 5-HETE (5-hydroxyeicosatetraenoic acid), HHT (12-hydroxyheptadecatrienoic acid), and thromboxane B2. These are products of the lipoxygenase and cyclooxygenase pathways of arachidonic acid metabolism. By inhibiting their formation, the compound may exert anti-inflammatory and anti-thrombotic effects. It is a resveratrol analog, suggesting it may also share some of resveratrol's biological activities.
ln Vitro
In vitro, 2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside inhibits the formation of 5-HETE, HHT, and thromboxane B2. These inhibitory effects are observed, although less strongly than some other compounds. It is a natural flavonoid glycoside from Polygonum species. Quantitative IC50 values for its inhibitory effects are not detailed in the publicly available sources.
ln Vivo
In vivo activity data for 2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside is limited in publicly available literature. As a compound with inhibitory effects on arachidonic acid metabolism in vitro, it is hypothesized to exhibit anti-inflammatory and anti-thrombotic effects in vivo. However, specific in vivo efficacy studies, including pharmacokinetic and pharmacodynamic parameters, have not been detailed in the available sources. Further research is needed to fully characterize its in vivo activity and therapeutic potential.
Enzyme Assay
For in vitro cell-free assays, the inhibitory activity of 2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside on 5-HETE, HHT, and thromboxane B2 formation can be studied using enzyme inhibition assays. The compound is incubated with the relevant enzymes (lipoxygenase, cyclooxygenase) and arachidonic acid substrate. The formation of products is measured by ELISA or HPLC. IC50 values are calculated from dose-response curves.
Cell Assay
For in vitro cellular assays, the anti-inflammatory and anti-thrombotic activities of 2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside can be assessed in relevant cell lines. Inflammatory cells (e.g., macrophages) can be treated with the compound and stimulated with LPS or other inflammatory stimuli. The production of inflammatory mediators (e.g., leukotrienes, thromboxanes) is measured by ELISA.
Animal Protocol
For in vivo studies, 2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside could be administered orally in animal models of inflammation or thrombosis. In inflammation models, endpoints include inflammatory biomarker levels and tissue histopathology. In thrombosis models, endpoints include thrombus formation and bleeding time.
ADME/Pharmacokinetics
2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside (CAS 82373-94-2) has a molecular formula of C20H22O9 and a molecular weight of 406.38 g/mol. Appearance: typically a powder. Solubility: DMSO and other organic solvents. Storage: typical for flavonoids (desiccated, protected from light, -20°C). Purity: 98%.
Toxicity/Toxicokinetics
No detailed toxicity data is publicly available. As a natural flavonoid glycoside from Polygonum multiflorum, it is generally considered to have low toxicity, but standard toxicological studies would be required for drug development. In vitro cytotoxicity assays in various cell lines are typically performed alongside efficacy studies.
References

[1]. Effects of stilbenes on arachidonate metabolism in leukocytes. Biochim Biophys Acta. 1985 Apr 25;834(2):275-8.

[2]. 2, 3, 5, 4'-Tetrahydroxystilbene-2-O-β-D-glucoside prevention of lipopolysaccharide-induced depressive-like behaviors in mice involves neuroinflammation and oxido-nitrosative stress inhibition. Behav Pharmacol. 2017 Aug;28(5):365-374.

[3]. Investigation on the mechanism of 2,3,4',5-Tetrahydroxystilbene 2-o-D-glucoside in the treatment of inflammation based on network pharmacology. Comput Biol Med. 2022 Jun;145:105448.

Additional Infomation
(E)-2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside is a stilbene compound formed by the substitution of hydroxyl groups at the 2', 3', 5', and 4' positions of trans-stilbene, with the hydroxyl group at the 2' position being converted to the corresponding β-D-glucoside. It possesses antioxidant, cyclooxygenase 2 inhibitory, anti-inflammatory, cardioprotective, platelet aggregation inhibitory, and apoptosis-inhibiting activities. It is a stilbene compound, a β-D-glucoside, belonging to the resorcinol class of compounds. (2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)vinyl]phenoxy]-6-(hydroxymethyl)oxacyclohexane-3,4,5-triol has been reported in Euphorbia marschalliana, Polygonaceae plants, and other organisms with relevant data. See also: Root (part) of Reynoutria multiflora.
2,3,5,4'-Tetrahydroxystilbene 2-O-β-D-glucoside is a research-grade compound and is not approved for therapeutic use. It serves primarily as a pharmacological tool for studying arachidonic acid metabolism, inflammation, and thrombosis. Its mechanism of action involves inhibition of 5-HETE, HHT, and thromboxane B2 formation. It is a natural product from Polygonum multiflorum, a traditional Chinese herbal medicine. No clinical trials have been reported.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H22O9
Molecular Weight
406.3833
Exact Mass
406.126
CAS #
82373-94-2
PubChem CID
5321884
Appearance
Light yellow to yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
715.0±60.0 °C at 760 mmHg
Flash Point
386.2±32.9 °C
Vapour Pressure
0.0±2.4 mmHg at 25°C
Index of Refraction
1.761
LogP
0.1
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
5
Heavy Atom Count
29
Complexity
536
Defined Atom Stereocenter Count
5
SMILES
C1=CC(=CC=C1/C=C/C2=C(C(=CC(=C2)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O
InChi Key
JAYVHSBYKLLDJC-DSNJPTTOSA-N
InChi Code
InChI=1S/C20H22O9/c21-9-15-16(25)17(26)18(27)20(28-15)29-19-11(7-13(23)8-14(19)24)4-1-10-2-5-12(22)6-3-10/h1-8,15-18,20-27H,9H2/b4-1+/t15-,16-,17+,18-,20+/m1/s1
Chemical Name
(2S,3R,4S,5S,6R)-2-[2,4-dihydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
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 : ~100 mg/mL (~246.08 mM)
H2O : ~10 mg/mL (~24.61 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.12 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 20.8 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: ≥ 2.08 mg/mL (5.12 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 20.8 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: ≥ 2.08 mg/mL (5.12 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 16.67 mg/mL (41.02 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.4608 mL 12.3038 mL 24.6075 mL
5 mM 0.4922 mL 2.4608 mL 4.9215 mL
10 mM 0.2461 mL 1.2304 mL 2.4608 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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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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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.

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