ChemicalBook--->CAS DataBase List--->27208-80-6

27208-80-6

27208-80-6 Structure

27208-80-6 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H319
[Precautionary statements ]

P264-P280-P305+P351+P338-P337+P313
[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 InformationBack 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. It scavenges DPPH (Item No. 14805) radicals and inhibits copper-induced lipid peroxidation (IC50s = 198 and 19.1 μM, respectively). Polydatin inhibits the proliferation of, and induces cell cycle arrest at the S phase in, Caco-2 colon cancer cells. 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.
[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
Spectrum DetailBack Directory
[Spectrum Detail]

Polydatin(27208-80-6)1HNMR
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