Basic information
- CAS
27208-80-6- 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- Molecular formula
- C20H22O8
- Average molar mass
- 390.4 g/mol
- Monoisotopic mass
- 390.13146766
Overview
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.
Names & identifiers
- Preferred 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
- English name
- Polydatin
- Molecular formula
- C20H22O8
- Molecular weight
- 390.39
Names & synonyms
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
Show more names
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)-
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 140 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 5
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 506
Experimental & physicochemical properties
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
Physicochemical properties
- Melting point
- 223 · 223-226 °C(lit.)
- Boiling point
- 707.7 · 707.7±60.0 °C(Predicted)
- alpha
- -77.5 · -77.5 º (c=0.2, EtOH)
- Density
- 1.521 · 1.521±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- DMSO, Ethanol, Methanol
- pka
- 9.21 · 9.21±0.10(Predicted)
Safety & regulation
GHS classification
GHS Classification
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]
Hazard information
Hazard Classes and Categories
Skin Irrit. 2 (100%)
Eye Irrit. 2 (100%)
Safety data
- wgk
- 3
- hs_code
- 29389090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionPolydatin 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.
UsesA Stilbenoid glucoside and is a major Resveratrol derivative.
Usesantioxidant
General DescriptionThis 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
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
南京丙承生物科技有限公司18805194892
Related reactions
2 records
Compound notes
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