Polydatin
[CAS 27208-80-6]

Identification

• Classification: Biochemical >> Natural biochemical product
• Name: Polydatin
• Synonyms: 3, 5, 4'-Trihydroxystilbene 3-glucoside; 3-Hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl-beta-D-glucopyranoside
• Molecular Formula: C₂₀H₂₂O₈
• Molecular Weight: 390.39
• CAS Registry Number: 27208-80-6
• EC Number: 683-198-7
• SMILES: C1=CC(=CC=C1/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O

Properties

• Density: 1.5±0.1 g/cm³ Calc.^*
• Melting point: 223 - 226 °C (Expl.)
• Boiling point: 707.7±60.0 °C 760 mmHg (Calc.)^*
• Flash point: 381.8±32.9 °C (Calc.)^*
• Index of refraction: 1.737 (Calc.)^*
• Alpha: -77.5 ° (c=0.2, EtOH) (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H315-H318-H319-H335
• Safety Statements: 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-P501

chemBlink Chemical Story

Polydatin, also known as trans-piceid, is a glucoside of resveratrol. A glucose residue is attached through oxygen at one of the phenolic positions of the stilbene. This is a covalent connection, so polydatin is not a mixture of resveratrol and glucose. The stilbene part still contains two aromatic rings linked by a double bond. The trans descriptor concerns arrangement around that bond, whereas the designation beta-D concerns the configuration of the sugar and its linkage. The two kinds of stereochemical information are independent.

Plant occurrence makes the distinction practical rather than merely a naming exercise. Polydatin has been recorded in Japanese knotweed and in grape products. A 1999 investigation measured both cis and trans forms of piceid and resveratrol in grape juices using liquid chromatography with spectral information. The work showed the importance of measuring the glucoside as well as the free compound when describing resveratrol-related constituents. A result about the sampled juices is not a guarantee of the profile of every grape product.

An analyst can ask two different questions about the same extract. One is how much intact polydatin is present. The other is how much resveratrol-related material becomes measurable after a treatment that cleaves the sugar linkage. Cleavage changes the species being counted. A number obtained after conversion must therefore be described differently from a measurement of the intact glucoside. Similarly, cis and trans compounds can have equal molecular masses, so a mass measurement by itself need not tell them apart.

Attaching glucose adds several hydroxyl groups and masks one phenolic oxygen in the linkage. These changes help explain why the intact glucoside and the free stilbene can behave differently in a separation. They do not by themselves predict how much of either species will reach a particular tissue after consumption. The chemical value of the example is that an apparently small change in how a plant packages a phenolic group can change the interpretation of an entire analysis.

References:
1. PubChem. Polydatin, CID 5281718. https://pubchem.ncbi.nlm.nih.gov/compound/5281718
2. Romero-Pérez AI et al. Piceid, the major resveratrol derivative in grape juices. J Agric Food Chem (1999). https://doi.org/10.1021/jf981024g

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