Oxyresveratrol
Oxyresveratrol
CAS: 29700-22-9;4721-07-7
Molecular Formula: C14H12O4
Oxyresveratrol - Names and Identifiers
| Name | Oxyresveratrol |
| Synonyms | Oxyresveratrol Oxy-Resveratrol 2,3',4,5'-Tetrahydroxy-trans-stilbene (E)-4-(3,5-dihydroxystyryl)benzene-1,3-diol 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol 4-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,3-diol Oxyresveratrol ,4-[(E)-2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,3-diol |
| CAS | 29700-22-9 4721-07-7 |
| EINECS | 608-401-8 |
| InChI | InChI=1/C14H12O4/c15-11-4-3-10(14(18)8-11)2-1-9-5-12(16)7-13(17)6-9/h1-8,15-18H/b2-1+ |
| InChIKey | PDHAOJSHSJQANO-OWOJBTEDSA-N |
Oxyresveratrol - Physico-chemical Properties
| Molecular Formula | C14H12O4 |
| Molar Mass | 244.24 |
| Density | 1.468±0.06 g/cm3(Predicted) |
| Melting Point | 201-202.5 °C |
| Boling Point | 523.8±30.0 °C(Predicted) |
| Flash Point | 260.9°C |
| Solubility | DMSO : ≥ 34 mg/mL (139.21 mM) |
| Vapor Presure | 1.37E-11mmHg at 25°C |
| Appearance | White-like powder |
| Color | Pale Yellow to Pale Beige |
| pKa | 9.14±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.8 |
| MDL | MFCD11974969 |
| Physical and Chemical Properties | White-like powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Polygonum cuspidatum. |
| In vitro study | Oxysveratrol inhibits amyloid beta-induced neurotoxicity, the in vitro activity of β-secretase, in cultured cortical neurons. In Cultured neuronal cells, neurotoxicity and DNA damage can also be prevented by its antioxidant activity. Oxysveratrol has moderate inhibitory activity against H5N1 neuraminidase. However, it has a strong inhibitory effect on α-glucosidase, an enzyme responsible for breaking down starch and polysaccharides into glucose in the intestinal tract. Oxyresveratrol is an effective radical scavenger. Oxysveratrol protects hepatocytes from oxidative stress, mitochondrial damage, and synthetic cell death. It can induce the activation of antioxidant transcription factor Nrf2 by ERK phosphorylation. |
| In vivo study | Oxysveratrol is extensively metabolized in the liver and rapidly eliminated by urination, so its short half-life in vivo limits its clinical application. In addition, its potential protective effect against neurodegenerative diseases is also hampered by its weak ability to penetrate the blood-brain barrier. Although the inhibitory activity against HSV-1 was weak in vitro, oxysveratrol, as an external emulsion, had high therapeutic efficacy in the mouse skin infection HSV1 model. Oxyresveratrol can ameliorate ccl4-induced acute liver injury. |
Oxyresveratrol - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36 - Irritating to the eyes |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29072990 |
Oxyresveratrol - Reference
| Reference Show more | 1. Fadhila, Mazaya, Abdul Mun’im, and Mahdi Jufri. "Ionic Liquid-based Microwave-Assisted Extraction (Il-MAE) of Oxyresveratrol from Morus alba Roots." Journal of Applied Pharmaceutical Science 8.06 (2018): 008-013. 10.7324/JAPS.2018.8602 2. Iswandana, Raditya, et al. "Application of Tween 80 and Tween 20 for microwave-assisted extraction of oxyresveratrol from mulberry (Morus alba L.) twigs." Journal of Applied Pharmaceutical Science 10.03 (2020): 093-100. 3. [IF=3.571] Ya-Nan Jia et al."Comparison of the Hepatoprotective Effects of the Three Main Stilbenes from Mulberry Twigs."J Agr Food Chem. 2019;67(19):5521–5529 |
Oxyresveratrol - Reference Information
| biological activity | Oxyresveratrol (Tetrahydroxystilbene, 2,3 ',4,5'-tetrahydroxystilbene) is a natural compound found from Morus alba L. It has an effective inhibitory effect on the dopa oxidase activity of tyrosinase and can catalyze the rate-limiting step of melanin biosynthesis. |
| target | TargetValue tyrosinase DPPH 28.9 μM |
| Target | Value |
| tyrosinase | |
| DPPH | 28.9 μM |
| in vitro study | Oxyresveratrol inhibit amyloid β protein-induced neurotoxicity and β-secretase in vitro activity in cultured cortical neurons. In cultured neuronal cells, neurotoxicity and DNA damage can also be prevented by its antioxidant activity. Oxyresveratrol had moderate inhibitory activity against H5N1 neuraminidase. But it has a strong inhibitory effect on α-glucosidase (the enzyme responsible for decomposing starch and polysaccharide into glucose in the intestine). Oxyresveratrol are effective free group scavengers. Oxyresveratrol can protect liver cells from oxidative stress, mitochondrial damage and synthetic cell death. It can induce the activation of antioxidant transcription factor Nrf2 through ERK phosphorylation. |
| in vivo research | Oxyresveratrol extensive metabolism in the liver and rapid elimination of urination, its in vivo half-life is short, limiting its clinical application. In addition, its potential protective effect against neurodegenerative diseases is also hindered by its weak ability to penetrate the blood-brain barrier. Although the inhibitory activity on HSV-1 in vitro is weak, oxyresveratrol as a topical emulsion, it has high therapeutic efficacy in the mouse skin infection HSV1 model. Oxyresveratrol can improve acute liver injury caused by CCl4. |
| chemical properties | white-like powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Polygonum cuspidatum. |
| use | used for content determination/identification/pharmacological experiments, etc. antioxidant, anti-inflammatory, antithrombotic, anti-cancer, anti-cancer, anti-hyperlipidemia, antibacterial and other activities |
Last Update：2024-04-09 20:49:11
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