| Identification | Back Directory | [Name]
rhapontigenin | [CAS]
500-65-2 | [Synonyms]
Protigenin
3-benzenediol
rhapontigenin
Rhapontigenin >
rhapontigenin USP/EP/BP
-5-(3-Hydroxy-4-methoxystyryl)
(E)-4'-Methoxy-3,3',5-stilbenetriol
3,3',5-Trihydroxy-4'-methoxy-trans-stilbene
5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-1
(E)-5-(3-Hydroxy-4-Methoxystyryl)benzene-1,3-diol
5-[2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
(E)-5-[2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol
5-[(1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL]-1;3-BENZENEDIOL
1,3-Benzenediol,5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]-
trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene
3,3',5-Trihydroxy-4'-methoxy-trans-stilbene
trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C15H14O4 | [MDL Number]
MFCD00017718 | [MOL File]
500-65-2.mol | [Molecular Weight]
258.272 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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] | [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) | [storage]
4°C, protect from light | [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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