Piceid

Piceid

IUPAC name 2-[3-Hydroxy-5-[(E)- 2-(4-hydroxyphenyl)ethenyl]phenoxy]- 6-(hydroxymethyl)oxane- 3,4,5-triol
Other names Polydatin Resveratrol 3-beta-mono-D-glucoside
Identifiers
CAS number	27208-80-6^Y
PubChem	5470020
UNII	XM261C37CQ^N
ChEMBL	CHEMBL142652^N
Jmol-3D images	Image 1
SMILES OC1=CC(/C=C/C3=CC=C(O) C=C3)=CC(O[C@H]2 [C@H](O)[C@@H](O) [C@H](O)[C@@H] (CO)O2)=C1
Properties
Molecular formula	C₂₀H₂₂O₈
Molar mass	390.384 g/mol
Exact mass	390.131468
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices.^[1] It can also be isolated from Polygonum cuspidatum^[2].

Trans-resveratrol-3-O-glucuronide is a metabolite of trans-resveratrol-3-O-glucoside.^[3]

References

^ Romero-Pérez AI, Ibern-Gómez M, Lamuela-Raventós RM, de La Torre-Boronat MC (April 1999). "Piceid, the major resveratrol derivative in grape juices". J. Agric. Food Chem. 47 (4): 1533–6. doi:10.1021/jf981024g. PMID 10564012.
^ PubChem
^ Simultaneous determination of trans-resveratrol-3-O-glucoside and its two metabolites in rat plasma using liquid chromatography with ultraviolet detection. Maojin Zhou, Xiaoyan Chen and Dafang Zhong, Journal of Chromatography B, Volume 854, Issues 1-2, 1 July 2007, pages 219-223, doi:10.1016/j.jchromb.2007.04.025

Stilbenoids and their glycosides

of resveratrol	Piceid \| Trans-resveratrol-3-O-glucuronide

Oligomeric forms

of resveratrol	Ampelopsin E \| Dimers : ε-viniferin, Parthenocissin A, Quadrangularin A, Pallidol and Amurensin A \| Trimers : α-viniferin, Laevifonol (an ε-viniferin-ascorbic acid hybrid compound), Malaysianol A, trans-diptoindonesin B \| Tetramers : Hopeaphenol \| Vitisins A, B and C

Oligomeric forms glycosides

Diptoindonesin A | Laevifoside (O-glucoside of ampelopsin A)

Misc

Synthetic

Stilbenoid drugs