| Identification | More | [Name]
Polydatin | [CAS]
27208-80-6 | [Synonyms]
3,4'-5-TRIHYDROXYSTILBENE-3-BETA-D-GLUCOPYRANOSIDE
3,4',5-TRIHYDROXYSTILBENE-3-BETA-MONOGLUCOSIDE
3, 5, 4'-trihydroxystilbene 3-glucoside
3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl-beta-D-glucopyranoside
3-HYDROXY-5-(2-(4-HYDROXYPHENYL)ETHENYL)PHENYL-BETA-D-GLUCOSIDE
4',5-DIHYDROXYSTILBENE-3-O-BETA-D-GLUCOSIDE
PICEID
POLYDATIN
RESVERATROL-3-B-D-GLUCOSIDE
RESVERATROL 3-BETA-MONO-D-GLUCOSIDE
RESVERATROL GLUCOSIDE
TRANS-RESVERATROL 3-O-BETA-D-GLUCURONIDE
TRANS-RESVERATROL-O-BETA-GLUCOSIDE
POLYDATIN(PICEID)(P)
TRANS-RESVERATROL-3-O-BETA-D-GLUCOSIDE
Polydatin
3-(β-D-Glucopyranosyloxy)-5-[(E)-2-(4-hydroxyphenyl)vinyl]phenol
Resveratrol 3-O-glucoside
trans-Resveratrol glucoside | [Molecular Formula]
C20H22O8 | [MDL Number]
MFCD00210592 | [Molecular Weight]
390.38 | [MOL File]
27208-80-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
223-226 °C(lit.) | [alpha ]
-77.5 º (c=0.2, EtOH) | [Boiling point ]
707.7±60.0 °C(Predicted) | [density ]
1.521±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO, Ethanol, Methanol | [form ]
Solid | [pka]
9.21±0.10(Predicted) | [color ]
Off-White | [λmax]
305nm(EtOH)(lit.) | [Major Application]
food and beverages | [InChI]
InChI=1/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/s3 | [InChIKey]
HSTZMXCBWJGKHG-RPHGGTSJNA-N | [SMILES]
O(C1C=C(O)C=C(/C=C/C2C=CC(O)=CC=2)C=1)[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O |&1:17,18,19,21,23,r| | [LogP]
0.412 (est) | [CAS DataBase Reference]
27208-80-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29389090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Description]
Polydatin is a stilbene glucoside and a precursor to trans-resveratrol (Item No. 70675) that has been found in V. vinifera and has diverse biological activities.1,2,3 It scavenges DPPH (Item No. 14805) radicals and inhibits copper-induced lipid peroxidation (IC50s = 198 and 19.1 μM, respectively).1 Polydatin inhibits the proliferation of, and induces cell cycle arrest at the S phase in, Caco-2 colon cancer cells.2 It decreases infarct size, cardiomyocyte fibrosis, and apoptosis in a mouse model of myocardial ischemia-reperfusion injury induced by left anterior descending (LAD) coronary artery occlusion when administered at a dose of 40 mg/kg per day.3 | [Chemical Properties]
Off-White Solid | [Uses]
A Stilbenoid glucoside and is a major Resveratrol derivative. | [Uses]
antioxidant | [Definition]
ChEBI: A stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue. | [General Description]
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG | [References]
[1] PIERRE WAFFO TEGUO. Isolation, Identification, and Antioxidant Activity of Three Stilbene Glucosides Newly Extracted from Vitis vinifera Cell Cultures[J]. Journal of Natural Products , 1998, 61 5: 655-657. DOI: 10.1021/np9704819
[2] SALVATORE DE MARIA. Polydatin, a natural precursor of resveratrol, induces cell cycle arrest and differentiation of human colorectal Caco-2 cell.[J]. Journal of Translational Medicine, 2013: 264. DOI: 10.1186/1479-5876-11-264
[3] MING D, SONGYAN L, YAWEN C, et al. trans-Polydatin protects the mouse heart against ischemia/reperfusion injury via inhibition of the renin–angiotensin system (RAS) and Rho kinase (ROCK) activity?[J]. Food & Function, 2017, 6: 2309-2321. DOI: 10.1039/c6fo01842d |
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