Piceid

Piceid

File:Piceid.svg 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 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8198 checkY
ChEMBL	ChEMBL142652 ☒N
ChemSpider	4445034 ☒N
ECHA InfoCard
E number
KEGG	C10275 checkY
PubChem CID	5281718
UNII	XM261C37CQ ☒N
CompTox Dashboard (EPA)	{{#property:P3117}}
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 ☒N Key: HSTZMXCBWJGKHG-CUYWLFDKSA-N ☒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). ☒N verify (what is checkY☒N ?) Infobox references

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

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

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.

Resveratrol glucoside from transgenic alfalfa prevents aberrant crypt foci in mice.

See also

• Resveratroloside (3,5,4'-trihydroxystilbene-4'-O-β-D-glucopyranoside)