rhapontin
glucopyranoside, rhapontigenin-3, beta-D-
 
Notes:
constituent of rhubarb rhizome.
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      Product(s):
      155-58-8 Rhaponticin
       
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CAS Number: 155-58-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 205-845-0
FDA UNII: K691M2Z08V
Nikkaji Web: J193.662J
MDL: MFCD00010117
XlogP3: 0.50 (est)
Molecular Weight: 420.41508000
Formula: C21 H24 O9
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
Google Books: Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Alfa Biotechnology
For experimental / research use only.
Rhapontin 98%
BOC Sciences
For experimental / research use only.
Rhaponticin
ExtraSynthese
For experimental / research use only.
Rhapontin (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Rhapontin 95%
Sigma-Aldrich
For experimental / research use only.
Rhapontin analytical standard
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 637213
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Chemidplus: 0000155588
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References:
 (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 637213
Pubchem (sid): 135033004
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C10288
HMDB (The Human Metabolome Database): Search
FooDB: FDB008525
Export Tariff Code: 2932.90.4100
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 rhubarb root
Search Trop  Picture
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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
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Articles:
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].
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