Piceid

Piceid
	250px; Trans-piceid
Names
	IUPAC names 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; Cis-piceid; trans-piceid; 3,5,4'-trihydroxystilbene-3-O-β-D-glucopyranoside
Identifiers
CAS Number	27208-80-6
ChEMBL	ChEMBL142652
ChemSpider	4445034
Jmol 3D model	Interactive image
PubChem	5281718
UNII	XM261C37CQ
	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	390.384 g/mol
Appearance	white powder
Vapor pressure	{{{value}}}
	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 Picea sitchensis.^[2] It can also be isolated from Polygonum cuspidatum,^[3] the Japanese knotweed (syn. Fallopia japonica).

Resveratrol can be produced from piceid fermented by Aspergillus oryzae.^[3] This latter species produces a piceid-b-D-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 has been used for the prevention of aberrant crypt foci in mice.^[6]

References

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↑ Purification and characterization of piceid-b-D-glucosidase from Aspergillus oryzae. Chunzhi Zhang, Dai Li, Hongshan Yu, Bo Zhang and Fengxie Jin, Process Biochemistry, 2007, 42, pages 83–88, doi:10.1016/j.procbio.2006.07.019
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Names
250px Trans-piceid
IUPAC names 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 Cis-piceid trans-piceid 3,5,4'-trihydroxystilbene-3-O-β-D-glucopyranoside
Identifiers
CAS Number	27208-80-6^Y
ChEMBL	ChEMBL142652^N
ChemSpider	4445034^N
Jmol 3D model	Interactive image
PubChem	5281718
UNII	XM261C37CQ^N
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	390.384 g/mol
Appearance	white powder
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references