27208-80-6

Basic information

• Product Name: Polydatin
• Synonyms: RESVERATROL GLUCOSIDE;RESVERATROL-3-B-D-GLUCOSIDE;RESVERATROL 3-BETA-MONO-D-GLUCOSIDE;TRANS-RESVERATROL 3-O-BETA-D-GLUCURONIDE;TRANS-RESVERATROL-O-BETA-GLUCOSIDE;3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl-beta-D-glucopyranoside;3-HYDROXY-5-(2-(4-HYDROXYPHENYL)ETHENYL)PHENYL-BETA-D-GLUCOSIDE;3, 5, 4'-trihydroxystilbene 3-glucoside
• CAS NO: 27208-80-6
• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.38
• Product Categories: Anthocyanins;The group of Polydatin;Nutritional Ingredients;Aromatics;Glucuronides;Heterocycles;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 27208-80-6.mol

Chemical Properties

• Melting Point: 223-226 °C(lit.)
• Boiling Point: 707.7 °C at 760 mmHg
• Flash Point: 381.8 °C
• Appearance: White fine powder
• Density: 1.521 g/cm³
• Vapor Pressure: 1.34E-20mmHg at 25°C
• Refractive Index: 1.69
• Storage Temp.: 0-10°C
• Solubility: DMSO, Ethanol, Methanol
• PKA: 9.21±0.10(Predicted)
• CAS DataBase Reference: Polydatin(CAS DataBase Reference)
• NIST Chemistry Reference: Polydatin(27208-80-6)
• EPA Substance Registry System: Polydatin(27208-80-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 27208-80-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 27208-80-6 differently. You can refer to the following data:
1. A Stilbenoid glucoside and is a major Resveratrol derivative.
2. 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

InChI:InChI=1/C21H24O8/c1-27-15-6-4-12(5-7-15)2-3-13-8-14(23)10-16(9-13)28-21-20(26)19(25)18(24)17(11-22)29-21/h2-10,17-26H,11H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1

Upstream product

• 94425-94-2 cis-3,5-dihydroxy-4'-methoxystilbene 3-O-β-D-glucopyranoside 
• 197440-96-3 (E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene 
• 30197-14-9 (E)-3-(β-D-glucopyranosyloxy)-5-hydroxy-4'-methoxystilbene 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 62502-04-9 (E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene 
• 5328-37-0 L-arabinose 
• 827348-01-6 (E)-1-{[3-tert-butyl(dimethyl)silyl]oxy}-5-hydroxyphenyl-2-({[4-tert-butyl(dimethyl)silyl]oxy}-phenyl)ethene 
• 2628-16-2 p-acetoxystyrene 
• 26153-38-8 3,5-dihydroxybenzaldehyde 
• 65728-21-4 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 824-94-2 p-methoxybenzyl chloride 
• 192710-89-7 cis-5-(4-methoxystyryl)benzene-1,3-diol 

Downstream Products

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 106822-44-0 (E)-1-(3-methoxy-5-(β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxyphenyl)ethene 
• 62502-04-9 (E)-1-(3-acetoxy-5-O-2,3,4,6-tetraacetyl-β-D-glucopyranosidophenyl)-2-(4'-acetoxyphenyl)ethene 

Relevant articles and documents

Enzymatic Synthesis of Resveratrol α-Glucoside by Amylosucrase of Deinococcus geothermalis

Glycosylation of resveratrol was carried out by using the amylosucrase of Deinococcus geothermalis, and the glycosylated products were tested for their solubility, chemical stability, and biological activities. We synthesized and identified these two major glycosylated products as resveratrol-4'-O- α-glucoside and resveratrol-3-O-α-glucoside by nuclear magnetic resonance analysis with a ratio of 5:1. The water solubilities of the two resveratrol-α-glucoside isomers (α-piceid isomers) were approximately 3.6 and 13.5 times higher than that of β-piceid and resveratrol, respectively, and they were also highly stable in buffered solutions. The antioxidant activity of the α-piceid isomers, examined by radical scavenging capability, showed it to be initially lower than that of resveratrol, but as time passed, the α-piceid isomers' activity reached a level similar to that of resveratrol. The α- piceid isomers also showed better inhibitory activity against tyrosinase and melanin synthesis in B16F10 melanoma cells than β-piceid. The cellular uptake of the α-piceid isomers, which was assessed by ultra-performance liquid chromatography (UPLC) analysis of the cell-free extracts of B16F10 melanoma cells, demonstrated that the glycosylated form of resveratrol was gradually converted to resveratrol inside the cells. These results indicate that the enzymatic glycosylation of resveratrol could be a useful method for enhancing the bioavailability of resveratrol.

Hybrid of Resveratrol and Glucosamine: An Approach to Enhance Antioxidant Effect against DNA Oxidation

Resveratrol exhibits various pharmacological activities, which are dependent upon phenolic hydroxyl groups. In this work, glucosamine, lipoic acid, or adamantanamine moiety was applied for attaching to ortho-position of hydroxyl group in resorcinol moiety of resveratrol (known as position-2). Antioxidant effects of the obtained hybrids were characterized using DNA oxidative systems mediated by ?OH, Cu2+/glutathione (GSH), and 2,2′-azobis(2-amidinopropanehydrochloride) (AAPH), respectively. The glucosyl-appended imine and amine at position-2 of resveratrol were found to show higher inhibitory effects than other resveratrol derivatives against AAPH-induced DNA oxidation. The antioxidative effect was quantitatively expressed by stoichiometric factor (n, the number of radical-propagation terminated by one molecule of antioxidant). The stoichiometric factors of glucosyl-appended imine and amine of resveratrol increased to 4.74 (for imine) and 4.97 (for amine), respectively, higher than that of resveratrol (3.70) and glucoside of resveratrol (3.49). It was thereby concluded that the combination of resveratrol with glucosamine at position-2 represented a novel pathway for modifying resveratrol structure in the protection of DNA against peroxyl radical-mediated oxidation.

Switching glycosyltransferase UGTBL1 regioselectivity toward polydatin synthesis using a semi-rational design

The 62nd residue of glycosyltransferase UGTBL1 was identified as a "hotspot" for glycosylation at 3-OH of resveratrol. Via semi-rational design including structure-guided alanine scanning and saturation mutations, the mutation I62G significantl

Synthesis, oxygen radical absorbance capacity, and tyrosinase inhibitory activity of glycosides of resveratrol, pterostilbene, and pinostilbene

The stilbene compound resveratrol was glycosylated to give its 4′-O-β-D-glucoside as the major product in addition to its 3-O-β-D-glucoside by a plant glucosyltransferase from Phytolacca americana expressed in recombinant Escherichia coli. This enzyme transformed pterostilbene to its 4′-O-β-D-glucoside, and converted pinostilbene to its 4′-O-β-D-glucoside as a major product and its 3-O-β-D-glucoside as a minor product. An analysis of antioxidant capacity showed that the above stilbene glycosides had lower oxygen radical absorbance capacity (ORAC) values than those of the corresponding stilbene aglycones. The 3-O-β-D-glucoside of resveratrol showed the highest ORAC value among the stilbene glycosides tested, and pinostilbene had the highest value among the stilbene compounds. The tyrosinase inhibitory activities of the stilbene aglycones were improved by glycosylation; the stilbene glycosides had higher activities than the stilbene aglycones. Resveratrol 3-O-β-D-glucoside had the highest tyrosinase inhibitory activity among the stilbene compounds tested.

Creating a Water-Soluble Resveratrol-Based Antioxidant by Site-Selective Enzymatic Glucosylation

The phytochemical resveratrol (trans-3,5,4′-trihydroxystilbene) has drawn great interest as health-promoting food ingredient and potential therapeutic agent. However, resveratrol shows vanishingly low water solubility; this limits its uptake and complicates the development of effective therapeutic forms. Glycosylation should be useful to enhance resveratrol solubility, with the caveat that unselective attachment of sugars could destroy the molecule's antioxidant activity. UGT71A15 (a uridine 5′-diphosphate α-D-glucose-dependent glucosyltransferase from apple) was used to synthesize resveratrol 3,5-β-D-diglucoside; this was about 1700-fold more water-soluble than the unglucosylated molecule (～0.18 mM), yet retained most of the antioxidant activity. Resveratrol 3-β-D-glucoside, which is the naturally abundant form of resveratrol, was a practical substrate for perfect site-selective conversion into the target diglucoside in quantitative yield (gL-1 concentration).

Exploring the catalytic promiscuity of a new glycosyltransferase from Carthamus tinctorius

The catalytic promiscuity of a new glycosyltransferase (UGT73AE1) from Carthamus tinctorius was explored. UGT73AE1 showed the capability to glucosylate a total of 19 structurally diverse types of acceptors and to generate O-, S-, and N-glycosides, making it the first reported trifunctional plant glycosyltransferase. The catalytic reversibility and regioselectivity were observed and modeled in a one-pot reaction transferring a glucose moiety from icariin to emodin. These findings demonstrate the potential versatility of UGT73AE1 in the glycosylation of bioactive natural products.

Assessing the regioselectivity of oleD-catalyzed glycosylation with a diverse set of acceptors

To explore the acceptor regioselectivity of OleD-catalyzed glucosylation, the products of OleD-catalyzed reactions with six structurally diverse acceptors flavonesnY (daidzein), isoflavones (flavopiridol), stilbenes (resveratrol), indole alkaloids (10-hydroxycamptothecin), and steroids (2- methoxyestradiol)- were determined. This study highlights the first synthesis of flavopiridol and 2-methoxyestradiol glucosides and confirms the ability of OleD to glucosylate both aromatic and aliphatic nucleophiles. In all cases, molecular dynamics simulations were consistent with the determined product distribution and suggest the potential to develop a virtual screening model to identify additional OleD substrates.

Glycosylation of trans-resveratrol by plant-cultured cells

Plant-cultured cells of Catharanthus roseus converted trans-resveratrol into its 3-O-β-D-glucopyranoside, 40-O-β-D-glucopyranoside, 3-O-(6-O-β-D-xylopyranosyl)-β-Dglucopyranoside, and 3-O-(6-O-α-L-arabinopyranosyl)-β- D-glucopyranoside. The 3-O-(6-O-β-D-x

Substrate specificities of family 1 UGTs gained by domain swapping

Family 1 glycosyltransferases are a group of enzymes known to embrace a large range of different substrates. This study devises a method to enhance the range of substrates even further by combining domains from different glycosyltransferases to gain impro

Regioselective glucosylation of aromatic compounds: Screening of a recombinant glycosyltransferase library to identify biocatalysts

(Chemical Equation Presented) A novel whole-cell screen for the identification of new glucosyltransferase (GT) biocatalysts within a recombinant enzyme library was developed. Following biotransformation, levels of D-glucose were used as a measure of biocatalysis. Twenty five enzymes that transfer D-glucose to trans-resveratrol were identified that have the regioselectivity shown in the picture.