Polydatin

Base Information

• Chemical Name: Polydatin
• CAS No.: 65914-17-2
• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.39
• Hs Code.: 29389090
• Mol file: 65914-17-2.mol

Synonyms:3,4'-5-Trihydroxystilbene-3-beta-D-glucopyranoside;Piceid;

Chemical Property of Polydatin

Chemical Property:

• 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: 9.31±0.10(Predicted)
• Flash Point: 381.8 °C
• PSA: 160.07000
• Density: 1.521 g/cm³
• LogP: 0.49640
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Ethanol (Sparingly), Methanol (Slightly), Water (Slightly)

Purity/Quality:

99% BY HPLC ^*data from raw suppliers

trans-Resveratrol 3-O-β-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: Polydatin (PD) is a major chemical component of Polygonum cuspidatum and it could also be found in a variety of other sources. PD is a polyphenol belonging to the chemical family of stilbenoids. Previous studies have shown that PD exhibits many pharmacological activities, including cardioprotective, neuroprotective, and antioxidative activities. With vascular dementia (VaD) rat models, PD markedly attenuated cognitive deficits. Biochemical analysis revealed that PD decreased the production of malondialdehyde (MDA) and significantly increased superoxide dismutase and catalase activities. Additionally, PD effectively alleviated the injuries of cultured neurons induced by oxygen–glucose deprivation. The therapeutic potential of PD for VaD seems related to its antioxidative activity and the direct protection of neurons. Furthermore, PD could also effectively inhibit the polymerization of amyloid-β peptides, which is a major mark in the progression of pathogenesis in Alzheimer’s disease (AD). These results suggest that PD is a promising drug candidate or nutraceutical for the treatment of VaD and AD. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside is a stilbene glucoside that has been found in V. vinifera and has diverse biological activities. It reduces the growth of SKOV3 ovarian cancer cell 3D aggregates in a concentration-dependent manner. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside (10 and 20 μg/ml) inhibits IL-17 production in activated peripheral blood mononuclear cells (PBMCs). It inhibits the loss of glutathione peroxidase 4 (GPX4) activity induced by the ferroptosis inducer hemin in Neuro2a neuroblastoma cells. 3,4′-5-Trihydroxystilbene-3-β-D-glucopyranoside (50 mg/kg) reduces escape latency in a rat model of vascular dementia induced by four-vessel occlusion (4-VO).
• Uses: Polydatin, a type of polyphenolic phytoalexin, has many physiological and pharmacological effects including anti-inflammatory and anti-oxidative activities. Polydatin is an effective candidate drug for the protection of photo-inflammation. Polydatin exhibits therapeutic potential for vascular dementia, most likely due to its anti-oxidant activity and the direct protection of neurons. 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 metabolite, a potassium channel modulator, an anti-arrhythmia drug, a hepatoprotective agent, an antioxidant and a nephroprotective agent. It is a stilbenoid, a polyphenol, a beta-D-glucoside and a monosaccharide derivative. It derives from a trans-resveratrol. Polydatin is a Resveratrol glycoside and inhibitor of platelet aggregation.
• Biological Functions: Stilbene found in medicinal herbs. Antioxidant, anti-inflammatory and neuroprotective.
• Clinical Use: Polydatin (PD, also named pieceid, (E)-piceid, (E)-polydatin, trans-polydatin, 3,40 ,5-trihydroxystilbene-3-b-D-glucoside) is a monocrystalline compound originally isolated from the root and rhizome of Polygonum cuspidatum Sieb. et Zucc. (Polygonaceae), a traditional Chinese medicine that has long been used in China as an analgesic, anti-pyretic, diuretic and expectorant. It is a glucoside of resveratrol (3,40 ,5-trihydroxystilbene) in which the glucoside group bound to the position C-3 substitutes a hydroxyl group, belonging to stilbene phytoalexins. Polydatin can also be detected in grape, peanut, hop cones, red wines, hop pellets, cocoa-containing products, chocolate products and many daily diets. Polydatin is the most abundant form of resveratrol in nature. Polydatin shows many pharmacological effects confirmed by numerous investigations, including cardiovascular protection, neuroprotection, anti-inflammation, immunoregulation, anti-oxidation, anti-tumour and liver and lung protective effects. Polydatin has found its way into clinical trials for the treatment of hemorrhagic shock and irritable bowel syndrome.

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)-astringin

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.