Piceid

Piceid
	Trans-piceid
Names
	IUPAC name 3-Hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]phenyl β-D-glucopyranoside
	Systematic IUPAC name (2S,3R,4S,5S,6R)-2-{3-Hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
	Other names Polydatin; Resveratrol 3-β-mono-D-glucoside; cis-Piceid; trans-Piceid; 3,5,4'-Trihydroxystilbene-3-O-β-D-glucopyranoside
Identifiers
CAS Number	27208-80-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8198 ;
ChEMBL	ChEMBL142652 ;
ChemSpider	4445034 ;
ECHA InfoCard	100.208.708
KEGG	C10275 ;
PubChem CID	5281718;
UNII	XM261C37CQ ;
CompTox Dashboard (EPA)	DTXSID001030555 DTXSID20897454, DTXSID001030555 ;
	InChI InChI=1S/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1 Key: HSTZMXCBWJGKHG-CUYWLFDKSA-N ; InChI=1/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/m1/s1 Key: HSTZMXCBWJGKHG-CUYWLFDKBI;
	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
Chemical formula	C20H22O8
Molar mass	390.388 g·mol−1
Appearance	White powder
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Piceid is a stilbenoid glucoside and is a major resveratrol derivative in grape juices.^[1] It can be found in the bark of the Sitka spruce (Picea sitchensis), hence its name.^[2] It can also be isolated from Japanese knotweed (Reynoutria japonica).^[3]

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Resveratrol can be produced from piceid by the mold Aspergillus oryzae,^[3] the mold used to make sake and soy sauce, as the fungus produces a potent beta-glucosidase.^[4]

trans-Piceid is the glucoside formed with trans-resveratrol, while cis-piceid is formed with cis-resveratrol.

trans-Resveratrol-3-O-glucuronide is one of the two metabolites of trans-piceid in rat.^[5]

Resveratrol glucoside from transgenic alfalfa prevents aberrant crypt foci in mice.^[6]

See also