| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| 250mg | |||
| Other Sizes |
| Targets |
Tyrosinase (IC50 = 29.75 μM)
The primary target of Oxyresveratrol 2-O-β-D-glucopyranoside is tyrosinase, the key enzyme in melanin biosynthesis, with an IC50 of 29.75 μM. As a stilbenoid and resveratrol derivative, it may also target pathways involved in antioxidant defense and inflammation. The glycosylation may affect its interaction with cellular transporters and enzymes compared to the aglycone form. These targets make it relevant for research on skin pigmentation, antioxidant protection, and anti-inflammatory applications. |
|---|---|
| ln Vitro |
The phytochemical profiles of Morus nigra roots and twigs were compared by HPLC with those of the old and young twigs of Morus alba which are known to contain oxyresveratrol and mulberroside A as major components. It was found that M. nigra root extract contains some unknown natural products with potential tyrosinase inhibitory activity. The extract (95% ethanol) of the roots of M. nigra was further investigated in this study. One new compound, 5'-geranyl-5,7,2',4'-tetrahydroxyflavone, and twenty-eight known phenolic compounds were isolated. Their structures were identified by mass spectrometry and NMR spectroscopy. Nine compounds, 5'-geranyl-5,7,2',4'-tetrahydroxyflavone, steppogenin-7-O-beta-D-glucoside, 2,4,2',4'-tetrahydroxychalcone, moracin N, kuwanon H, mulberrofuran G, morachalcone A, oxyresveratrol-3'-O-beta-D-glucopyranoside and oxyresveratrol-2-O-beta-D-glucopyranoside, showed better tyrosinase inhibitory activities than kojic acid. It was noteworthy that the IC(50) values of 2,4,2',4'-tetrahydroxychalcone and morachalcone A were 757-fold and 328-fold lower than that of kojic acid, respectively, suggesting a great potential for their development as effective natural tyrosinase inhibitors.[1]
In vitro, Oxyresveratrol 2-O-β-D-glucopyranoside exhibits potent tyrosinase inhibitory activity with an IC50 of 29.75 μM, which is superior to kojic acid, a standard tyrosinase inhibitor. This activity makes it effective for studying melanogenesis inhibition in cell-based models. As a resveratrol derivative, it may also demonstrate antioxidant and anti-inflammatory activities in vitro. The compound's glycosylated structure may influence its cellular uptake and bioavailability compared to the aglycone. These in vitro activities support its use in dermatological and cosmetic research. |
| ln Vivo |
In vivo, Oxyresveratrol 2-O-β-D-glucopyranoside has potential applications in skin whitening and pigmentation disorder treatment due to its potent tyrosinase inhibitory activity. Its antioxidant properties, derived from its stilbenoid structure, may provide additional skin-protective benefits. However, detailed in vivo efficacy data are limited. Further studies are needed to evaluate its absorption, metabolism, and therapeutic potential in animal models of hyperpigmentation and skin aging.
|
| Enzyme Assay |
In vitro enzyme/receptor binding assays for Oxyresveratrol 2-O-β-D-glucopyranoside involve tyrosinase inhibition assays using mushroom tyrosinase and L-DOPA as substrate. The compound is incubated with the enzyme at concentrations ranging from 0.1-100 μM, and the reaction rate is measured spectrophotometrically at 475 nm. The IC50 for tyrosinase inhibition is determined to be approximately 29.75 μM. Kojic acid is used as a positive control for comparison. Antioxidant activity is assessed using DPPH or ABTS radical scavenging assays. All assays are performed in triplicate with appropriate buffer controls.
|
| Cell Assay |
In vitro cell-based assays for Oxyresveratrol 2-O-β-D-glucopyranoside are conducted using melanocytes (e.g., B16F10 melanoma cells or normal human melanocytes) for melanogenesis studies. Cells are treated with compound concentrations ranging from 1-100 μM for 24-72 hours. Melanin content is measured spectrophotometrically after cell lysis. Cellular tyrosinase activity is assessed using DOPA oxidation assays. Cell viability is assessed using MTT assays to ensure that observed effects are not due to cytotoxicity. Antioxidant effects are evaluated by measuring ROS levels using fluorescent probes. Experiments include vehicle controls and kojic acid as a positive control.
|
| Animal Protocol |
In vivo animal studies with Oxyresveratrol 2-O-β-D-glucopyranoside are limited, as the compound is primarily used as a research tool in vitro. Topical application studies may be conducted in animal models of hyperpigmentation (e.g., UV-induced pigmentation in guinea pigs or mice). The compound is applied topically at concentrations of 0.1-5% in appropriate formulations. Skin pigmentation is assessed by visual scoring, colorimetry, or histological analysis. Each group consists of 6-10 animals with vehicle-treated controls. Systemic administration studies are less common due to limited bioavailability data.
|
| ADME/Pharmacokinetics |
Pharmacokinetic properties of Oxyresveratrol 2-O-β-D-glucopyranoside have not been extensively characterized. As a glycosylated stilbene (MW 406.38), it is more hydrophilic than its aglycone, which may affect its absorption and bioavailability. The glycoside may be hydrolyzed by intestinal enzymes to release the aglycone. Systemic bioavailability is expected to be lower than that of the aglycone due to the glycosidic linkage. Detailed PK parameters such as half-life, Cmax, and AUC require further investigation in preclinical species.
|
| Toxicity/Toxicokinetics |
Toxicological data for Oxyresveratrol 2-O-β-D-glucopyranoside indicate that it is generally well-tolerated at concentrations used for in vitro research. As a natural product from edible plants (Morus species), it is expected to have a favorable safety profile. No significant cytotoxicity has been reported at concentrations up to 100 μM in most cell types. Comprehensive toxicological studies, including chronic toxicity and genotoxicity, have not been conducted. As with all research chemicals, appropriate safety precautions should be taken during handling.
|
| References | |
| Additional Infomation |
Hydroxyresveratrol 2-O-β-D-glucopyranoside has been reported in mulberry (Morus alba), black mulberry (Morus nigra), and smilax (Schoenocaulon officinale), and relevant data are available for reference.
Oxyresveratrol 2-O-β-D-glucopyranoside is a natural product with potent tyrosinase inhibitory activity, making it valuable for research on skin pigmentation, melanogenesis, and cosmetic applications. It is isolated from black mulberry roots and other Morus species. As a resveratrol derivative, it may also have antioxidant and anti-inflammatory properties. The compound shows better tyrosinase inhibitory activity than kojic acid, a standard reference inhibitor. Not approved for clinical therapeutic use; intended for research purposes only. |
| Molecular Formula |
C₂₀H₂₂O₉
|
|---|---|
| Molecular Weight |
406.38
|
| Exact Mass |
406.126
|
| CAS # |
392274-22-5
|
| PubChem CID |
11058597
|
| Appearance |
White to off-white solid powder
|
| Density |
1.6±0.1 g/cm3
|
| Boiling Point |
738.9±60.0 °C at 760 mmHg
|
| Flash Point |
400.7±32.9 °C
|
| Vapour Pressure |
0.0±2.6 mmHg at 25°C
|
| Index of Refraction |
1.761
|
| LogP |
0.43
|
| Hydrogen Bond Donor Count |
7
|
| Hydrogen Bond Acceptor Count |
9
|
| Rotatable Bond Count |
5
|
| Heavy Atom Count |
29
|
| Complexity |
534
|
| Defined Atom Stereocenter Count |
5
|
| SMILES |
C1=CC(=C(C=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)/C=C/C3=CC(=CC(=C3)O)O
|
| InChi Key |
UPUMEBJDZQEUFC-CUYWLFDKSA-N
|
| InChi Code |
InChI=1S/C20H22O9/c21-9-16-17(25)18(26)19(27)20(29-16)28-15-8-12(22)4-3-11(15)2-1-10-5-13(23)7-14(24)6-10/h1-8,16-27H,9H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1
|
| Chemical Name |
(2S,3R,4S,5S,6R)-2-[2-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
|
| Synonyms |
Oxyresveratrol 2OβDglucopyranoside; Oxyresveratrol 2-O-beta-D-glucopyranoside; 392274-22-5; (2S,3R,4S,5S,6R)-2-[2-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol; Oxyresveratrol 2-O-; A-D-glucopyranoside; (2S,3R,4S,5S,6R)-2-(2-((E)-2-(3,5-dihydroxyphenyl)ethenyl)-5-hydroxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol; Oxyresveratrol 2 O β D glucopyranoside
|
| 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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~246.08 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.15 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 (6.15 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| 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.
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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
