rhapontigenin
rhapontigenin Basic information
- Product Name:
- rhapontigenin
- Synonyms:
-
- 3-benzenediol
- 5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1
- 5-[(1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL]-1;3-BENZENEDIOL
- 5-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
- rhapontigenin
- (E)-5-[2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol
- 3,3',5-Trihydroxy-4'-methoxy-trans-stilbene trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene
- (E)-4'-Methoxy-3,3',5-stilbenetriol
- CAS:
- 500-65-2
- MF:
- C15H14O4
- MW:
- 258.27
- EINECS:
- 1312995-182-4
- Mol File:
- 500-65-2.mol
rhapontigenin Chemical Properties
- Melting point:
- 189.0 to 193.0 °C
- Boiling point:
- 503.6±38.0 °C(Predicted)
- Density
- 1.345±0.06 g/cm3(Predicted)
- storage temp.
- 4°C, protect from light
- solubility
- ≤30mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
- form
- powder to crystal
- pka
- 9.17±0.10(Predicted)
- color
- White to Light yellow
- InChI
- 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+
- InChIKey
- PHMHDRYYFAYWEG-NSCUHMNNSA-N
- SMILES
- C1(O)=CC(/C=C/C2=CC=C(OC)C(O)=C2)=CC(O)=C1
- CAS DataBase Reference
- 500-65-2
rhapontigenin Usage And Synthesis
Description
Rhapontigenin is a natural analog of resveratrol and an inhibitor of CYP1A1.
Description
Rhapontigenin is a natural analog of resveratrol with antioxidant and anti-
Chemical Properties
Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from Rheum officinale.
Uses
Rhapontigenin is a natural analog of resveratrol with antioxidant and anti-cancer activity. It is a mechanism-based, selective inactivator of cytochrome P450 1A1 (IC50 = 400 nM), an aryl hydrocarbon hydroxylase which activates polycyclic aromatic hydrocarbons that act as procarcinogens. At higher concentrations, rhapontigenin inhibits the proliferation of HepG2 and HL-60R cancer cell lines (IC50 = 48 μM).[Cayman Chemical]
Uses
Rhapontigenin is a natural analog of resveratrol and an inhibitor of CYP1A1.
Definition
ChEBI: Rhapontigenin is a stilbenoid.
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. |
IC 50
CYP1A1: 400 nM (IC50)
References
[1]. chun yj, ryu sy, jeong tc, et al. mechanism-based inhibition of human cytochrome p450 1a1 by rhapontigenin. drug metab dispos. 2001 apr;29(4 pt 1):389-93.
[2]. roberti m1, pizzirani d, simoni d, et al. synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents. j med chem. 2003 jul 31;46(16):3546-54.
[3]. roupe ka1, helms gl, halls sc, 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.
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rhapontigenin(500-65-2)Related Product Information
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