A stilbenoid glycoside
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Rhapontin

Item No. 19867

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl-β-D-glucopyranoside
CAS Number
155-58-8
Synonyms
  • NSC 43321
  • Rhaponticin
  • trans-Rhapontin
Molecular Formula
C21H24O9
Formula Weight
420.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMF:PBS(pH 7.2)(1:6): 0.14 mg/mlDMSO: 30 mg/ml
λmax
220, 325 nm
SMILES
OC1=CC(/C=C/C2=CC(O)=CC(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)=C2)=CC=C1OC
InChi Code
InChI=1S/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1
InChi Key
GKAJCVFOJGXVIA-DXKBKAGUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    10 mg

    $36

    Add

    50 mg

    $103

    Add

    100 mg

    $176

    Add

    250 mg

    $393

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    Rhapontin is a natural stilbenoid glycoside first isolated from rhubarb rhizomes. It is converted by glucosidases to rhapontigenin (Item No. 13293), a resveratrol analog with antioxidant and anti-cancer activity.1,2,3 Rhapontigenin derived enzymatically from rhapontin has also been found to have antibiotic activity as well as inhibit melanin synthesis.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chun, Y.J., Ryu, S.Y., Jeong, T.C., et al. Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin. Drug Metab. Dispos. 29(4), 389-393 (2001).

    2. Roupe, K.A., Helms, G.L., Halls, S.C., et al. Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: Applications to metabolism, pharmacokinetics and anti-cancer studies. J. Pharm. Pharm. Sci. 8(3), 374-386 (2005).

    3. Roberti, M., Pizzirani, D., Simoni, D., et al. Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. J. Med. Chem. 46(16), 3546-3554 (2003).

    4. Kim, J.-K., Kim, N., and Lim, Y.-H. Evaluation of the antibacterial activity of rhapontigenin produced from rhapontin by biotransformation against Propionibacterium acnes. J. Microbiol. Biotechnol. 20(1), 82-87 (2010).

    5. Lee, H.-S., Kim, J.-K., Park, K.-T., et al. Rhapontigenin converted from rhapontin purified from Rheum undulatum enhances the inhibition of melanin synthesis. Biosci. Biotechnol. Biochem. 76(12), 2307-2309 (2012).