trans-Resveratrol-3-O-glucuronide

trans-Resveratrol-3-O-glucuronide is a metabolite of resveratrol[1] and trans-resveratrol-3-O-glucoside (piceid).[2][3]

trans-Resveratrol-3-O-glucuronide
Names
IUPAC name
3-Hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]phenyl β-D-glucopyranosiduronic acid
Systematic IUPAC name
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]phenoxy}oxane-2-carboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C20H20O9/c21-12-5-3-10(4-6-12)1-2-11-7-13(22)9-14(8-11)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h1-9,15-18,20-25H,(H,26,27)/b2-1+/t15-,16-,17+,18-,20+/m0/s1
    Key: QWSAYEBSTMCFKY-OTPOQTMVSA-N
  • InChI=1/C20H20O9/c21-12-5-3-10(4-6-12)1-2-11-7-13(22)9-14(8-11)28-20-17(25)15(23)16(24)18(29-20)19(26)27/h1-9,15-18,20-25H,(H,26,27)/b2-1+/t15-,16-,17+,18-,20+/m0/s1
    Key: QWSAYEBSTMCFKY-OTPOQTMVBZ
  • O=C(O)[C@H]3O[C@@H](Oc2cc(O)cc(\C=C\c1ccc(O)cc1)c2)[C@H](O)[C@@H](O)[C@@H]3O
Properties
C20H20O9
Molar mass 404.371 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Urpi-Sarda, M.; Zamora-Ros, R.; Lamuela-Raventos, R.; Cherubini, A.; Jauregui, O.; De La Torre, R.; Covas, M. I.; Estruch, R.; Jaeger, W.; Andres-Lacueva, C. (2006). "HPLC-Tandem Mass Spectrometric Method to Characterize Resveratrol Metabolism in Humans". Clinical Chemistry. 53 (2): 292–299. doi:10.1373/clinchem.2006.071936. PMID 17170057.
  2. Zhou, M.; Chen, X.; Zhong, D. (2007). "Simultaneous determination of trans-resveratrol-3-O-glucoside and its two metabolites in rat plasma using liquid chromatography with ultraviolet detection". Journal of Chromatography B. 854 (1–2): 219–223. doi:10.1016/j.jchromb.2007.04.025. PMID 17500049.
  3. Mikulski, D.; Molski, M. (2010). "Quantitative structure–antioxidant activity relationship of trans-resveratrol oligomers, trans-4,4′-dihydroxystilbene dimer, trans-resveratrol-3-O-glucuronide, glucosides: Trans-piceid, cis-piceid, trans-astringin and trans-resveratrol-4′-O-β-D-glucopyranoside". European Journal of Medicinal Chemistry. 45 (6): 2366–2380. doi:10.1016/j.ejmech.2010.02.016. PMID 20199826.


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