A stilbene and an active metabolite of trans-resveratrol
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trans-Resveratrol-3-O-β-D-Glucuronide

Item No. 13832

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-hydroxy-5-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenyl-β-D-glucopyranosiduronic acid
CAS Number
387372-17-0
Synonyms
  • Resveratrol 3-O-D-Glucuronide
Molecular Formula
C20H20O9
Formula Weight
404.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlMethanol: 5 mg/ml
λmax
217, 307, 320 nm
SMILES
O[C@H]1[C@H](O)[C@@H](O)[C@H](OC2=CC(/C=C/C3=CC=C(O)C=C3)=CC(O)=C2)O[C@@H]1C(O)=O
InChi Code
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
InChi Key
QWSAYEBSTMCFKY-CTAHFCQASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $134

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    1 mg

    $253

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    5 mg

    $1,058

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    Product Description

    trans-Resveratrol-3-O-β-D-glucuronide is a stilbene that has been found in red wine and an active metabolite of trans-resveratrol (Item No. 70675), a polyphenol with diverse biological activities.1 It is primarily produced from trans-resveratrol by the UDP-glucuronosyltransferase (UGT) isoform UGT1A1.2 trans-Resveratrol-3-O-β-D-glucuronide binds to COX-1 (IC50 = 150 µM).3 It reduces the proliferation of several intestinal cancer cell lines (IC50s = 10-16.5 µM) and induces cell cycle arrest at the G0/G1 phase in SW480 intestinal cancer cells when used at a concentration of 30 µM.4 trans-Resveratrol-3-O-β-D-glucuronide (200 µM) increases pyruvate production in livers isolated from rats in a model of arthritis induced by complete Freund's adjuvant (CFA).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Potter, G.A., Patterson, L.H., Wanogho, E., et al. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYPIBI. Br. J. Cancer 86(5), 774-778 (2002).

    2. Aumont, V., Krisa, S., Battaglia, E., et al. Regioselective and stereospecific glucuronidation of trans- and cis-resveratrol in human. Arch. Biochem. Biophys. 393(2), 281-289 (2001).

    3. Calamini, B., Ratia, K., Malkowski, M.G., et al. Pleiotropic mechanisms facilitated by resveratrol and its metabolites. Biochem. J. 429(2), 273-282 (2012).

    4. Polycarpou, E., Meira, L.B., Carrington, S., et al. Resveratrol 3-O-D-glucuronide and resveratrol 4'-O-D-glucuronide inhibit colon cancer cell growth: evidence for a role of A3 adenosine receptors, cyclin D1 depletion, and G1 cell cycle arrest. Mol. Nutr. Food Res. 57(10), 1708-1717 (2013).

    5. Simões, M.S., Ames-Sibin, A.P., Lima, E.P., et al. Resveratrol biotransformation and actions on the liver metabolism of healthy and arthritic rats. Life Sci. 310, 120991 (2022).