155-58-8

Basic information

• Product Name: RHAPONTIN
• Synonyms: 3,3',5-TRIHYDROXY-4'-METHOXY-STILBENE 3-O-BETA-D-GLUCOSIDE;4'-METHOXY-3,3',5-STILBENETRIOL-3-GLUCOSIDE;4'-METHOXY-3,3',5-STILBENETROL;RHAPONTICIN;RHAPONTIN;3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)vinyl]phenyl-beta-D-glucopyranoside;RHAPONTIN FROM RHUBARB ROOT;3,3',5-trihydroxy-4'-methoxystilbene 3-o-β-d-glucoside
• CAS NO: 155-58-8
• Molecular Formula: C₂₁H₂₄O₉
• Molecular Weight: 420.41
• EINECS: 205-845-0
• Product Categories: Miscellaneous Natural Products;Cardioglycosides & Glycosides
• Mol File: 155-58-8.mol

Chemical Properties

• Melting Point: 236-240 °C
• Boiling Point: 457.61°C (rough estimate)
• Flash Point: 406.9 °C
• Appearance: light yellow
• Density: 1.2828 (rough estimate)
• Vapor Pressure: 1.39E-23mmHg at 25°C
• Refractive Index: 1.6230 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Acetone (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 9.16±0.10(Predicted)
• Stability: Hygroscopic
• Merck: 13,8258
• CAS DataBase Reference: RHAPONTIN(CAS DataBase Reference)
• NIST Chemistry Reference: RHAPONTIN(155-58-8)
• EPA Substance Registry System: RHAPONTIN(155-58-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 24/25-37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 155-58-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Rhapontin is used as an inhibitor for tyrosinase, which is responsible for the molting process in insects. By inhibiting this enzyme, Rhapontin can help regulate and control the molting process, making it a valuable compound in the development of pharmaceutical solutions for insect-related conditions.
Used in Agriculture:
In the agricultural industry, Rhapontin is utilized as a preventative agent against the undesirable browning of fruits and vegetables. The inhibition of tyrosinase by Rhapontin helps maintain the freshness and visual appeal of these produce items, reducing waste and enhancing their marketability.
Used in Cosmetics Industry:
Rhapontin is employed in the cosmetics industry as a skin-lightening agent. By inhibiting tyrosinase, which is involved in the coloring of skin, hair, and eyes in animals, Rhapontin can help reduce the appearance of pigmentation and promote an even skin tone.
Used in Food Industry:
In the food industry, Rhapontin serves as a natural additive to prevent the browning of fruits and vegetables during processing and storage. This helps maintain the quality and color of these products, ensuring a longer shelf life and improved consumer appeal.

InChI:InChI=1/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1

Upstream product

• 621-58-9 3-hydroxy-4-methoxystyrene 
• 709030-16-0 (3-hydroxy-5-iodophenyl) 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 604-68-2 α-D-glucopyranose peracetylate 
• 10272-07-8 3.5-dimethoxyaniline 
• 25245-27-6 1-iodo-3,5-dimethoxybenzene 
• 621-59-0 isovanillin 
• 94356-23-7 rhaponticin 6-gallate 
• 94356-24-8 rhaponticin 2-gallate 
• 94356-25-9 rhaponticin 2''-O-p-coumarate 
• 124530-57-0 Rhaponticin 6''-O-(E)-p-coumarate 

Downstream Products

• 113042-92-5 Acetic acid (2R,3S,4R,5S,6S)-3,5-diacetoxy-2-{3-acetoxy-5-[(E)-2-(3-acetoxy-4-methoxy-phenyl)-vinyl]-phenoxy}-6-acetoxymethyl-tetrahydro-pyran-4-yl ester 
• 1403836-09-8 rhaponticin 
• 1093135-92-2 C₄₇H₆₇NO₂₉ 
• 266997-55-1 (2S,3R,4S,5R,6R)-2-{3-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-5-methoxy-phenoxy}-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran 
• 500-65-2 rhapontigenin 
• 94356-30-6 cis-3,3',5-trihydroxy-4'-methoxystilbene 3-O-β-D-glucopyranoside 
• 113042-92-5 (E)-3,3'-diacetoxy-4'-methoxy-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene 

Related news

Protective role of RHAPONTIN (cas 155-58-8) in experimental pulmonary fibrosis in vitro and in vivo09/29/2019

Pulmonary fibrosis is a scaring process related to chronic lung injury of all causes. The treatment options for pulmonary fibrosis are very limited. Rhapontin has anti-inflammatory effect and anti-proliferative activity which is widely distributed in the medicinal plants of Rheum genus in China....detailed

RHAPONTIN (cas 155-58-8) ameliorates colonic epithelial dysfunction in experimental colitis through SIRT1 signaling09/28/2019

Rhapontin (3, 3′, 5-trihydroxy-4′-methoxystilbene-3-O-glucoside) has anti-thrombotic, anti-allergic and anti-diabetic activities. This study aimed to assess the protective effects of rhapontin on intestinal damage in vivo and in vitro. In a dextran sodium sulfate (DSS)-induced mouse model, ora...detailed

Relevant articles and documents

A short synthesis of rhaponticin and its 3''-fluoroanalog via a wittig/heck-mizoroki route

Rhaponticin and its 3''-fluoroanalog have been prepared from easily accessible starting materials. The key step of these syntheses is the silver carbonate-mediated glycosidation reaction employed for the selective formation of a β -glycosidic bond. A palladium acetate-catalyzed Heck-Mizoroki reaction in triethanolamine established an (E) configuration in the stilbene with simultaneous deprotection of the carbohydrate.

USE OF HYDROXYSTILBENES FOR DYEING, READY-TO-USE COMPOSITION CONTAINING THEM AND DYEING PROCESS

The invention relates to the use of hydroxystilbenes for dyeing, to ready-to-use dye compositions comprising them, to a dyeing process using them and to a multi-compartment device containing the compositions used in the processes of the invention.

Studies on Rhubarb (Rhei Rhizoma). VI. Isolation and Characterization of Stilbenes

Nineteen stilbene derivatives (I-XIX), of which five are novel cis-stilbenes, have been obtained from a rhubarb of low quality (commercial name:, Imo-Daio).Based on chemical and spectroscopic evidence, these compounds have been characterized as rhapontigenin (I), rhaponticin (II), rhapontigenin 3'-O-β-D-glucopyranoside (III), rhaponticin 6''-O-gallate (IV), rhaponticin 2''-O-gallate (V), rhaponticin 2''-O-p-coumarate (VI), piceatannol (VII), piceatannol 3-O-β-D-glucopyranoside (VIII), piceatannol 3'-O-β-D-glucopyranoside (IX), piceatannol 3'-O-β-D-xylopyranoside (X), piceatannol 3-O-β-D-(6''-O-galloyl) glucopyranoside (XI), desoxyrhaponticin (XII), desoxyrhaponticin 6''-O-gallate (XIII), 3,4',5-trihydroxystilbene 4'-O-β-D-(6''-O-galloyl) glucopyranoside (XIV), cis-3,3',5-trihydroxy-4'-methoxystilbene 3-O-β-D-glucopyranoside (XV), cis-3,3',5-trihydroxy-4'-methoxystilbene 3-O-β-D-(6''-O-galloyl) glucopyranoside (XVI), cis-3,5-dihydroxy-4'-methoxystilbene 3-O-β-D-glucopyranoside (XVII), cis-3,3',5-trihydroxy-4'-methoxystilbene 3-O-β-D-(2''-O-galloyl) glucopyranoside (XVIII) and cis-3,3',5-trihydroxy-4'-methoxystilbene (XIX).Keywords - rhubarb; Polygonaceae; trans-stilbene; cis-stilbene; gallic acid ester; p-coumaric acid ester; rhaponticin; desoxyrhaponticin; piceatannol; 3,4',5-trihydroxystilbene