Polydatin

Base Information

• Chemical Name: Polydatin
• CAS No.: 27208-80-6
• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.39
• Hs Code.: 29389090
• Mol file: 27208-80-6.mol

Synonyms:Piceid(6CI,7CI,8CI);b-D-Glucopyranoside,3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenyl, (E)-;(E)-Piceid;(E)-Polydatin;(E)-Resveratrol 3-O-b-D-glucopyranoside;3-Hydroxy-5-(p-hydroxystyryl)phenyl b-D-glucoside;Polydotin peceid;Resveratrol 3-O-b-glucopyranoside;trans-Piceid;trans-Polydatin;

Chemical Property of Polydatin

Chemical Property:

• Appearance/Colour: White fine powder
• Vapor Pressure: 1.34E-20mmHg at 25°C
• Melting Point: 223-226 °C(lit.)
• Refractive Index: 1.69
• Boiling Point: 707.7 °C at 760 mmHg
• PKA: 9.21±0.10(Predicted)
• Flash Point: 381.8 °C
• PSA: 139.84000
• Density: 1.521 g/cm³
• LogP: 0.44690
• Storage Temp.: 0-10°C
• Solubility.: DMSO, Ethanol, Methanol

Purity/Quality:

98%, ^*data from raw suppliers

transResveratrol3-O-β-D-glucopyranoside,98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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 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.
• Uses: A Stilbenoid glucoside and is a major Resveratrol derivative. antioxidant

Technology Process of Polydatin

There total 34 articles about Polydatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(E)-1-[3-{[tert-butyl(dimethyl)silyl]oxy}-5-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethene (892402-77-6) → polydatin (27208-80-6,65914-17-2,148766-36-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; methanol; at 0 - 25 ℃; for 5h;

DOI:10.1055/s-2006-926394

Reference yield: 94.0%

(E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene (62502-04-9) → polydatin (27208-80-6,65914-17-2,148766-36-3)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 1h;

DOI:10.1081/SCC-120030744

Reference yield: 60.0%

(E)-3-(β-D-glucopyranosyloxy)-5-hydroxy-4'-methoxystilbene (30197-14-9,65830-63-9,94425-94-2) → polydatin (27208-80-6,65914-17-2,148766-36-3)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; at 140 ℃; for 10h;

DOI:10.1016/S0008-6215(97)00087-6

upstream raw materials:

cis-3,5-dihydroxy-4'-methoxystilbene 3-O-β-D-glucopyranoside

(E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene

(E)-3-(β-D-glucopyranosyloxy)-5-hydroxy-4'-methoxystilbene

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

Downstream raw materials:

(E)-1-(3-methoxy-5-(β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxyphenyl)ethene

cis-piceid

β-D-glucose

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

Refernces

• 1、 Fan, Bo,Dong, Wenxin,Chen, Tianyi,Chu, Jianlin,He, Bingfang. "Switching glycosyltransferase UGTBL1 regioselectivity toward polydatin synthesis using a semi-rational design". supporting information. p. 2464 - 2469. Retrieved 2018/04/12.
• 2、 Uesugi, Daisuke,Hamada, Hiroki,Shimoda, Kei,Kubota, Naoji,Ozaki, Shin-Ichi,Nagatani, Naoki. "Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene". . p. 226 - 230. Retrieved 2017/01/24.