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MedKoo Cat#: 146201 | Name: Rhapontin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rhapontin is a natural stilbene glycoside found primarily in rhubarb species, such as Rheum rhaponticum. It possesses various biological activities, including antioxidant, anti-inflammatory, and phytoestrogenic effects. Rhapontin exerts its effects by modulating estrogen receptors and inhibiting oxidative stress pathways, making it a potential therapeutic agent for menopausal symptoms and hormone-related disorders. It is also being explored for use in nutraceuticals and functional foods.

Chemical Structure

Rhapontin
Rhapontin
CAS#155-58-8

Theoretical Analysis

MedKoo Cat#: 146201

Name: Rhapontin

CAS#: 155-58-8

Chemical Formula: C21H24O9

Exact Mass: 420.1420

Molecular Weight: 420.41

Elemental Analysis: C, 60.00; H, 5.75; O, 34.25

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Rhapontin;
IUPAC/Chemical Name
(2S,3R,4S,5S,6R)-2-(3-hydroxy-5-((E)-3-hydroxy-4-methoxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
InChi Key
GKAJCVFOJGXVIA-DXKBKAGUSA-N
InChi Code
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
SMILES Code
COC1=CC=C(\C=C\C2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2)C=C1O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 420.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Wei W, Wang L, Zhou K, Xie H, Zhang M, Zhang C. Rhapontin ameliorates colonic epithelial dysfunction in experimental colitis through SIRT1 signaling. Int Immunopharmacol. 2017 Jan;42:185-194. doi: 10.1016/j.intimp.2016.11.024. Epub 2016 Dec 5. PMID: 27930969. 2: Jo SP, Kim JK, Lim YH. Antihyperlipidemic effects of rhapontin and rhapontigenin from rheum undulatum in rats fed a high-cholesterol diet. Planta Med. 2014 Aug;80(13):1067-71. doi: 10.1055/s-0034-1382999. Epub 2014 Aug 15. PMID: 25127020. 3: Tao L, Cao J, Wei W, Xie H, Zhang M, Zhang C. Protective role of rhapontin in experimental pulmonary fibrosis in vitro and in vivo. Int Immunopharmacol. 2017 Jun;47:38-46. doi: 10.1016/j.intimp.2017.03.020. Epub 2017 Mar 30. PMID: 28364627. 4: Lee HS, Kim JK, Park KT, Lim YH. Rhapontigenin converted from rhapontin purified from Rheum undulatum enhances the inhibition of melanin synthesis. Biosci Biotechnol Biochem. 2012;76(12):2307-9. doi: 10.1271/bbb.120229. Epub 2012 Dec 7. PMID: 23221688. 5: Zeng Q, Hu H, Huang Z, Guo A, Lu S, Tong W, Zhang Z, Shen T. Active and machine learning-enhanced discovery of new FGFR3 inhibitor, Rhapontin, through virtual screening of receptor structures and anti-cancer activity assessment. Front Mol Biosci. 2024 Jun 11;11:1413214. doi: 10.3389/fmolb.2024.1413214. PMID: 38919748; PMCID: PMC11196408. 6: Hibasami H, Takagi K, Ishii T, Tsujikawa M, Imai N, Honda I. Induction of apoptosis by rhapontin having stilbene moiety, a component of rhubarb (Rheum officinale Baillon) in human stomach cancer KATO III cells. Oncol Rep. 2007 Aug;18(2):347-51. PMID: 17611655. 7: AlAjmi MF, Azhar A, Hasan S, Alshabr AZ, Hussain A, Rehman MT. Identification of natural compounds (proanthocyanidin and rhapontin) as high-affinity inhibitors of SARS-CoV-2 Mpro and PLpro using computational strategies. Arch Med Sci. 2021 Mar 20;20(2):567-581. doi: 10.5114/aoms/133706. PMID: 38757037; PMCID: PMC11094827. 8: Kim JK, Kim N, Lim YH. Evaluation of the antibacterial activity of rhapontigenin produced from rhapontin by biotransformation against Propionibacterium acnes. J Microbiol Biotechnol. 2010 Jan;20(1):82-7. PMID: 20134237. 9: Chen D, Liu JR, Cheng Y, Cheng H, He P, Sun Y. Metabolism of Rhaponticin and Activities of its Metabolite, Rhapontigenin: A Review. Curr Med Chem. 2020;27(19):3168-3186. doi: 10.2174/0929867326666190121143252. PMID: 30666906. 10: Liu L, Liu H, Yan H, Guo H, Bai L. Separation and purification of glycosides from medicinal plants based on strong polar separation medium with online closed-loop mode. J Pharm Biomed Anal. 2023 Sep 20;234:115508. doi: 10.1016/j.jpba.2023.115508. Epub 2023 Jun 7. PMID: 37295190. 11: Rehman A, Ashfaq UA, Javed MR, Shahid F, Noor F, Aslam S. The Screening of Phytochemicals Against NS5 Polymerase to Treat Zika Virus Infection: Integrated Computational Based Approach. Comb Chem High Throughput Screen. 2022;25(4):738-751. doi: 10.2174/1386207324666210712091920. PMID: 34254908. 12: Wang LX, Zhang BC, Li LP, Zhou Z. [Quantitative determination of rhapontin in root of Rheum hotaoense by TLC-scanning]. Zhongguo Zhong Yao Za Zhi. 1994 Jan;19(1):37, 62. Chinese. PMID: 8011123. 13: Zhao XH, Han F, Li YL, Yue HL. Preparative isolation and purification of three stilbene glycosides from the tibetan medicinal plant Rheum tanguticum maxim. Ex Balf. by high-speed counter-current chromatography. Phytochem Anal. 2013 Feb;24(2):171-5. doi: 10.1002/pca.2397. Epub 2012 Aug 31. PMID: 22936596. 14: Li CL, Ye YW. [Effects of rhapontin of rheum hotaoense on serum lipid and lipoprotein levels (serum)]. Yao Xue Xue Bao. 1981 Sep;16(9):699-702. Chinese. PMID: 7331819. 15: Ouyang X, Li X, Liu J, Liu Y, Xie Y, Du Z, Xie H, Chen B, Lu W, Chen D. Structure-activity relationship and mechanism of four monostilbenes with respect to ferroptosis inhibition. RSC Adv. 2020 Aug 21;10(52):31171-31179. doi: 10.1039/d0ra04896h. PMID: 35520676; PMCID: PMC9056428. 16: Gao S, Yuan S, Quan Y, Jin W, Shen Y, Li R, Liu B, Wang Y, Yi L, Wang S, Hou X, Wang Y. Targeting AI-2 quorum sensing: harnessing natural products against Streptococcus suis biofilm infection. Vet Res. 2025 Feb 4;56(1):26. doi: 10.1186/s13567-025-01450-x. PMID: 39905565; PMCID: PMC11796197. 17: Lam RY, Woo AY, Leung PS, Cheng CH. Antioxidant actions of phenolic compounds found in dietary plants on low-density lipoprotein and erythrocytes in vitro. J Am Coll Nutr. 2007 Jun;26(3):233-42. doi: 10.1080/07315724.2007.10719606. PMID: 17634168. 18: Kim N, Kim JK, Hwang D, Lim YH. The possible mechanism of rhapontigenin influencing antifungal activity on Candida albicans. Med Mycol. 2013 Jan;51(1):45-52. doi: 10.3109/13693786.2012.689021. Epub 2012 Jun 4. PMID: 22662760. 19: Peigen X, Liyi H, Liwei W. Ethnopharmacologic study of Chinese rhubarb. J Ethnopharmacol. 1984 May;10(3):275-93. doi: 10.1016/0378-8741(84)90016-3. PMID: 6748707. 20: Yang T, Wang Q, Qu Y, Feng C, Li C, Yang Y, Sun Z, Alahmadi TA, Alharbi SA, Bao S. Protective effect of rhaponticin on ovariectomy-induced osteoporosis in rats. J Biochem Mol Toxicol. 2021 Sep;35(9):e22837. doi: 10.1002/jbt.22837. Epub 2021 Jul 5. PMID: 34227182.