rhapontin
glucopyranoside, rhapontigenin-3, beta-D-
Identification
| Name | rhapontin |
| IUPAC | (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol |
| CAS Number | 155-58-8 |
| EINECS | 205-845-0 |
| FDA UNII | K691M2Z08V |
| Molecular Formula | C21 H24 O9 |
| Molecular Weight | 420.41508000 |
| MDL Number | MFCD00010117 |
| Nikkaji Number | J193.662J |
| XlogP3 | 0.50 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 749.30 °C. @ 760.00 mm Hg (est) |
| Flash Point | 764.00 °F. TCC ( 406.90 °C. ) (est) |
| logP (o/w) | 0.680 (est) |
| Soluble in | water, 1484 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for rhapontin usage levels up to | not for fragrance use. |
| Recommendation for rhapontin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
beta-d-
glucopyranoside, 3-hydroxy-5-(2-(3-hydroxy-4-methoxyphenyl)ethenyl)phenyl (9CI)
glucopyranoside, rhapontigenin-3, beta-D-
3-
hydroxy-5-(2-(3-hydroxy-4-methoxyphenyl)ethenyl)phenyl-beta-d-glucopyranoside
3-
hydroxy-5-(2-(3-hydroxy-4-methoxyphenyl)vinyl)phenyl-beta-D-glucopyranoside
(2S,3R,4S,5S,6R)-2-[3-
hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
ponticin
rhaponticin
rhaponticine
rhapontigenin, 3-beta-D-glucopyranoside
PubMed:
Antihyperlipidemic effects of rhapontin and rhapontigenin from rheum undulatum in rats fed a high-cholesterol diet.
PubMed:
[Study on preparation of deoxyrhaponti-beta-cyclodextrin super-molecular inclusion complex and performance of inclusion complex].
PubMed:
Inhibitory effect of desoxyrhaponticin and rhaponticin, two natural stilbene glycosides from the Tibetan nutritional food Rheum tanguticum Maxim. ex Balf., on fatty acid synthase and human breast cancer cells.
PubMed:
Enhanced pharmacokinetics and anti-tumor efficacy of PEGylated liposomal rhaponticin and plasma protein binding ability of rhaponticin.
PubMed:
Quantitative assessment of traditional Oriental herbal formulation Samhwangsasim-tang using UPLC technique.
PubMed:
A simple and rapid spectrofluorimetric method for determining the pharmacokinetics and metabolism of rhaponticin in rat plasma, feces and urine using a cerium probe.
PubMed:
Rhapontigenin converted from rhapontin purified from Rheum undulatum enhances the inhibition of melanin synthesis.
PubMed:
Solvent effects on the absorption and fluorescence spectra of rhaponticin: experimental and theoretical studies.
PubMed:
Synthesis and biological evaluation of a folate-targeted rhaponticin conjugate.
PubMed:
Preparative isolation and purification of three stilbene glycosides from the tibetan medicinal plant Rheum tanguticum maxim. Ex Balf. by high-speed counter-current chromatography.
PubMed:
Magnetic molecularly imprinted polymer for the detection of rhaponticin in Chinese patent medicines.
PubMed:
The possible mechanism of rhapontigenin influencing antifungal activity on Candida albicans.
PubMed:
One-step preparative separation of two polyhydroxystilbenes from Rheum likiangense Sam. by high-speed counter-current chromatography.
PubMed:
Pharmacokinetics, bioavailability and metabolism of rhaponticin in rat plasma by UHPLC-Q-TOF/MS and UHPLC-DAD-MSn.
PubMed:
Studies on the binding of rhaponticin with human serum albumin by molecular spectroscopy, modeling and equilibrium dialysis.
PubMed:
[Binding mechanism of rhaponticin and human serum albumin].
PubMed:
Chemical-based species classification of rhubarb using simultaneous determination of five bioactive substances by HPLC and LDA analysis.
PubMed:
Assessment for the light-induced cis-trans isomerization of rhapontigenin and its glucoside rhaponticin by capillary electrophoresis and spectrometric methods.
PubMed:
Regulating volume transitions of highly responsive hydrogel scaffolds by adjusting the network properties of microgel building block colloids.
PubMed:
Evaluation of the antibacterial activity of rhapontigenin produced from rhapontin by biotransformation against Propionibacterium acnes.
PubMed:
Rhaponticin from rhubarb rhizomes alleviates liver steatosis and improves blood glucose and lipid profiles in KK/Ay diabetic mice.
PubMed:
Coumarin, anthroquinone and stilbene derivatives with anticholinesterase activity.
PubMed:
Polymer-associated liposomes as a novel delivery system for cyclodextrin-bound drugs.
PubMed:
Antioxidant actions of phenolic compounds found in dietary plants on low-density lipoprotein and erythrocytes in vitro.
PubMed:
Induction of apoptosis by rhapontin having stilbene moiety, a component of rhubarb (Rheum officinale Baillon) in human stomach cancer KATO III cells.
PubMed:
Protective effect of rhubarb derivatives on amyloid beta (1-42) peptide-induced apoptosis in IMR-32 cells: a case of nutrigenomic.
PubMed:
Desoxyrhaponticin (3,5-dihydroxy-4'-methoxystilbene 3-O-beta-D-glucoside) inhibits glucose uptake in the intestine and kidney: In vitro and in vivo studies.
PubMed:
Insulin sensitizing and alpha-glucoamylase inhibitory action of sennosides, rheins and rhaponticin in Rhei Rhizoma.
PubMed:
[Determination of six effective components in Rheum by cyclodextrin modified micellar electrokinetic chromatography].
PubMed:
[A new ecdysone hormone rhaponticum from Rhaponticum uniflorum (L.) DC].
PubMed:
Antithrombotic and antiallergic activities of rhaponticin from Rhei Rhizoma are activated by human intestinal bacteria.
PubMed:
Stable isotope labeling pattern of resveratrol and related natural stilbenes.
PubMed:
Downregulation of the cyclin D1/Cdk4 complex occurs during resveratrol-induced cell cycle arrest in colon cancer cell lines.
PubMed:
Metabolism of rhaponticin and chrysophanol 8-o-beta-D-glucopyranoside from the rhizome of rheum undulatum by human intestinal bacteria and their anti-allergic actions.
PubMed:
Inhibitory effects of hydroxystilbenes on cyclooxygenase from sheep seminal vesicles.
PubMed:
[Quantitative determination of rhapontin in root of Rheum hotaoense by TLC-scanning].
PubMed:
[Determination of anthraquinone derivatives in rhubarb grown for export].
PubMed:
Ethnopharmacologic study of Chinese rhubarb.
PubMed:
[Effects of rhapontin of rheum hotaoense on serum lipid and lipoprotein levels (serum)].
PubMed:
Substrate specificity in vivo and in vitro in the formation of stilbenes. Biosynthesis of rhaponticin.
PubMed:
[A preliminary study of the correlation between phylogeny, chemical constituents and therapeutic effects of Rheum species].