Polydatin

HCID 5281718CAS 27208-80-6

Teilstruktursuche Ähnliche Strukturen suchen

Grundinformationen

Standard-SMILES: OC[C@H]1O[C@@H](Oc2cc(O)cc(/C=C/c3ccc(O)cc3)c2)[C@H](O)[C@@H](O)[C@@H]1O
InChIKey: HSTZMXCBWJGKHG-CUYWLFDKSA-N
Summenformel: C20H22O8
Durchschnittliche Molmasse: 390,4 g/mol
Monoisotopische Masse: 390,13146766

Überblick

Trans-piceid is a stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue. It has a role as a geroprotector, an antioxidant, a metabolite, an anti-arrhythmia drug, a potassium channel modulator, a hepatoprotective agent and a nephroprotective agent. It is a beta-D-glucoside, a polyphenol, a stilbenoid and a monosaccharide derivative. It is functionally related to a trans-resveratrol.

Namen und Bezeichner

Bevorzugter Name: Polydatin
IUPAC: (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Englischer Name: Polydatin
Summenformel: C20H22O8
Molmasse: 390.39

Namen und Synonyme

Piceid27208-80-6Trans-Piceid3,4,5-Trihydroxystilbene-3-beta-monoglucoside3,4,5-TsgResveratrol 3-beta-mono-D-glucosideResveratrol 3-O-beta-glucopyranosideXM261C37CQ3,4'-5-Trihydroxystilbene-3-beta-D-glucopyranosideresveratrol 3-O-beta-D-glucosidetrans-resveratrol 3-beta-glucosidetrans-resveratrol 3-beta-D-glucoside

Weitere Namen anzeigen

Resveratrol 3-O-β-D-glucopyranoside(2S,3R,4S,5S,6R)-2-(3-Hydroxy-5-((E)-4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolPieceidPlydatinPiceid>(E)-Piceidrans-picei(E)-PolydatinPolydatin CRStrans-Polydatin

trans-resveratrol 3-O-beta-D-glucosideCHEBI:81983,4',5-trihydroxystilbene-3-beta-D-glucoside3-Hydroxy-5-(2-(4-hydroxyphenyl)ethenyl)phenyl-beta-D-glucosidebeta-D-Glucopyranoside, 3-hydroxy-5-(2-(4-hydroxyphenyl)ethenyl)phenylbeta-D-Glucopyranoside, 3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenylPolydatin (E)-polydatin, (E)-

Datenbank-Bezeichner

CAS: 27208-80-6、65914-17-2
PubChem CID: 5281718
DTXSID: DTXSID001030555
ChEMBL: CHEMBL142652
ChEBI: CHEBI:8198
UNII: XM261C37CQ
EC Number: 111-790-2、683-198-7
Nikkaji: J17.288J、J9.897C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,7
Polarare Oberfläche (TPSA): 140 Å²
H-Brücken-Donoren: 6
H-Brücken-Akzeptoren: 8
Frei drehbare Bindungen: 5
Schwere Atome: 28
Formalladung: 0
Komplexität: 506

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Diphenyl ethers, biphenyls, dibenzyls and stilbenes [PK1309]

Endocrine DisruptorsPotential endocrine disrupting compound

Melting Point130 - 140 °C

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt: 223 · 223-226 °C(lit.)
Siedepunkt: 707.7 · 707.7±60.0 °C(Predicted)
Dichte: 1.521 · 1.521±0.06 g/cm3(Predicted)
storage temp.: 2 · Sealed in dry,2-8°C
Löslichkeit: DMSO, Ethanol, Methanol
pka: 9.21 · 9.21±0.10(Predicted)
Aggregatzustand: Solid
Farbe: Off-White
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 · 0.412 (est)
CAS Datenbank: 27208 · 27208-80-6(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Gefahrenhinweise

Hazard Classes and Categories · 2 Einträge

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

Sicherheitsdaten

wgk: 3
hs_code: 29389090
safety_code: 22-24/25
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Eye Irrit. 2

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsCytoplasm

Anwendungen · 2 Einträge

BeschreibungPolydatin 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 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.

VerwendenA Stilbenoid glucoside and is a major Resveratrol derivative.