CAS Number500-65-2
Synonymstrans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene; 5-[(E)-2-(3-Hydroxy-4-methoxyphenyl)vinyl]-1,3-benzenediol; rhapontigenin; 5-[(E)-2-(3-Hydroxy-4-methoxyphenyl)vinyl]benzene-1,3-diol; (E)-5-(3-Hydroxy-4-methoxystyryl)benzene-1,3-diol; 3,3',5-Trihydroxy-4'-methoxy-trans-stilbene; 5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
Molecular FormulaC15H14O4
Molecular Weight258.27
Purity≥98.0 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point503.6±38.0 °C at 760 mmHg
Melting Point186-187ºC
AppearanceWhite, light gray crystal powder
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 500-65-2 |
| Catalog No. | 2A-9022309 |
| Chinese Name | 丹叶大黄素 |
| Synonyms | trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene; 5-[(E)-2-(3-Hydroxy-4-methoxyphenyl)vinyl]-1,3-benzenediol; rhapontigenin; 5-[(E)-2-(3-Hydroxy-4-methoxyphenyl)vinyl]benzene-1,3-diol; (E)-5-(3-Hydroxy-4-methoxystyryl)benzene-1,3-diol; 3,3',5-Trihydroxy-4'-methoxy-trans-stilbene; 5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol |
| Molecular Formula | C15H14O4 |
| Molecular Weight | 258.27 |
| Purity | ≥98.0 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 503.6±38.0 °C at 760 mmHg |
| Melting Point | 186-187ºC |
| Appearance | White, light gray crystal powder |
| Storage Condition | 0-10°C; store in inert gas; avoid light, air, heat |
| Application | Rhapontigenin is a natural analog of resveratrol with anticancer, antioxidant, antifungal and antibacterial activity. Rhapontigenin is a potent and selective inhibitor of cytochrome P450 1A1 (IC50=400 |
| MDL Number | MFCD00017718 |
| SMILES | O(C)c1c(cc(cc1)\C=C\c2cc(cc(c2)O)O)O |
| InChI | 1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+ |
| InChI Key | PHMHDRYYFAYWEG-NSCUHMNNSA-N |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| MSDS | msds/22309_1_500_65_2.pdf |
| Bioactivity | Rhapontigenin is a natural analog of resveratrol with anticancer, antioxidant, antifungal and antibacterial activities. Rhapontigenin is amechanism-based, potent and selective cytochrome P450 1A1 inactivator (IC50 = 400 nM). Rhapontigenin exhibits 400-fold and 23-fold selectivity for P450 1A1 over P450 1A2 and P450 1B1, respectively[1]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450 Research Areas >> Inflammation/Immunology Target CYP1A1:400 nM (IC50) In Vitro Rhapontigenin (0-250 μM; 24 hours) demonstrates concentration-dependent anti-cancer activity with an IC50 115μM in HEP G2 cells[1]. Rhapontigenin (20 μM; 20 hours) pre-treatment decreases TGF-β triggered increased snail expression in diverse cancer cells[2]. Rhapontigenin (0-20 μM; 6 hours) inhibits TGF-β-induced expression of N-cadherin, vimentin, and CA9 in a dose-dependent manner[2]. Rhapontigenin inhibits ADP- and collagen-induced platelet aggregation with IC50 values of 4 and 70 μg/ml, respectively[3]. Rhapontigenin demonstrates a strong inhibitory activity on the 13-hexosaminidase release induced by DNP-BSA, it exhibits IC50 value of 0.03 mM in RBL 2H3 cells[3]. Western Blot Analysis[2] Cell Line: HeLa, A549,769-P cells Concentration: 0 μM; 2.5 μM; 5 μM; 10 μM; 20 μM Incubation Time: 6 hours Result: Induced ubiquitination and degradation of HIF-1α. In Vivo Rhapontigenin (intraperitoneal injection; 25mg/kg) shows significant protection from death due to pulmonary thrombosis in mice, those samples are orally administered 90 min before tail vein injection of epinephrine and collagen[3]. Animal Model: ICR mice[3] Dosage: 25mg/kg Administration: 25mg/kg; intraperitoneal injection Result: Showed anti-thrombosis activity with 60% protection. References [1]. Roupe KA, et al. Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: applications to metabolism, pharmacokinetics and anti-cancer studies.J Pharm Pharm Sci. 2005 Aug 22;8(3):374-86. [2]. Yeh YH, et al. Rhapontigenin inhibits TGF-β-mediated epithelial‑mesenchymal transition via the PI3K/AKT/mTOR pathway and is not associated with HIF-1α degradation.Oncol Rep. 2016 May;35(5):2887-95. [3]. Park EK, et al. Antithrombotic and antiallergic activities of rhaponticin from Rhei Rhizoma are activated by human intestinal bacteria.Arch Pharm Res. 2002 Aug;25(4):528-33. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 503.6±38.0 °C at 760 mmHg Melting Point 186-187ºC Molecular Formula C15H14O4 Molecular Weight 258.269 Flash Point 258.4±26.8 °C Exact Mass 258.089203 PSA 69.92000 LogP 2.82 Vapour Pressure 0.0±1.3 mmHg at 25°C Index of Refraction 1.722 |
| Use of | Rhapontigenin is a natural analog of resveratrol with anticancer, antioxidant, antifungal and antibacterial activities. Rhapontigenin is amechanism-based, potent and selective cytochrome P450 1A1 inactivator (IC50 = 400 nM). Rhapontigenin exhibits 400-fold and 23-fold selectivity for P450 1A1 over P450 1A2 and P450 1B1, respectively[1]. Properties Name Rhapontigenin Synonym More Synonyms Rhapontigenin Biological Activity Description Rhapontigenin is a natural analog of resveratrol with anticancer, antioxidant, antifungal and antibacterial activities. Rhapontigenin is amechanism-based, potent and selective cytochrome P450 1A1 inactivator (IC50 = 400 nM). Rhapontigenin exhibits 400-fold and 23-fold selectivity for P450 1A1 over P450 1A2 and P450 1B1, respectively[1]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450 Research Areas >> Inflammation/Immunology CYP1A1:400 nM (IC50) References [1]. Roupe KA, et al. Preparative enzymatic synthesis and HPLC analysis of rhapontigenin: applications to metabolism, pharmacokinetics and anti-cancer studies.J Pharm Pharm Sci. 2005 Aug 22;8(3):374-86. [2]. Yeh YH, et al. Rhapontigenin inhibits TGF-β-mediated epithelial‑mesenchymal transition via the PI3K/AKT/mTOR pathway and is not associated with HIF-1α degradation.Oncol Rep. 2016 May;35(5):2887-95. [3]. Park EK, et al. Antithrombotic and antiallergic activities of rhaponticin from Rhei Rhizoma are activated by human intestinal bacteria.Arch Pharm Res. 2002 Aug;25(4):528-33. Chemical & Physical Properties Molecular Formula C15H14O4 Exact Mass 258.089203 PSA 69.92000 Index of Refraction 1.722 |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified |
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