84954-92-7

Basic information

• Product Name: ROSAVIN
• Synonyms: b-D-Glucopyranoside,(2E)-3-phenyl-2-propen-1-yl 6-O-a-L-arabinopyranosyl-;(2E)-3-Phenylprop-2-en-1-yl 6-O-α-L-arabinopyranosyl-β-D-glucopyranoside;(2R,3R,4S,5S,6R)-2-[(E)-3-Phenylprop-2-enoxy]-6-([(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl)oxane-3,4,5-triol;(E)-3-Phenyl-2-propenyl 6-O-a-L-arabinopyranosyl-β-D-glucopyranoside;(2R,3R,4S,5S,6R)-2-(CinnAmyloxy)-6-((((2R,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)o;ROSAVIN;[(E)-3-Phenyl-2-propenyl]6-O-(α-L-arabinopyranosyl)-β-D-glucopyranoside;[(E)-3-Phenyl-2-propenyl]6-O-α-L-arabinopyranosyl-β-D-glucopyranoside
• CAS NO: 84954-92-7
• Molecular Formula: C₂₀H₂₈O₁₀
• Molecular Weight: 428.43
• Product Categories: standardized herbal extract;Miscellaneous Natural Products;Natural Plant Extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).
• Mol File: 84954-92-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 171～173℃
• Boiling Point: 709.1 °C at 760 mmHg
• Flash Point: 382.6 °C
• Appearance: white to beige/
• Density: 1.48 g/cm³
• Vapor Pressure: 4.21E-21mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: ?20°C
• Solubility: H2O: ≥5mg/mL (warmed)
• PKA: 12.89±0.70(Predicted)
• CAS DataBase Reference: ROSAVIN(CAS DataBase Reference)
• NIST Chemistry Reference: ROSAVIN(84954-92-7)
• EPA Substance Registry System: ROSAVIN(84954-92-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 84954-92-7(Hazardous Substances Data)

Usage

Uses

Rosavin is a glycoside antioxidant from Rhadiola rosea that exhibits antidepressant, anxiolytic and adaptogenic properties.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Rosavin is a well-known glycoside antioxidant from Rhadiola rosea (Golden Root, or Arctic Root) that exhibits antidepressant, anxiolytic and adaptogenic properties.

InChI:InChI=1/C20H28O10/c21-12-9-28-19(17(25)14(12)22)29-10-13-15(23)16(24)18(26)20(30-13)27-8-4-7-11-5-2-1-3-6-11/h1-7,12-26H,8-10H2/b7-4+/t12-,13+,14-,15+,16-,17+,18+,19-,20-/m0/s1

Upstream product

• 1083195-64-5 ethyl 2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 869848-87-3 2,3,4-tri-O-acetyl-α/β-L-arabinopyranosyl trichloroacetimidate 
• 14206-56-5 2,3,4-tri-O-benzoyl-β-L-arabinopyranosyl bromide 
• 2595-07-5 allyl β-D-glucopyranoside 
• 866325-72-6 allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside 
• 866325-70-4 allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside 
• 866325-71-5 allyl 6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 
• 14260-08-3 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6')-(1',2',3',4'-tetra-O-acetyl-β-D-glucopyranoside) 
• 916494-81-0 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl-(1->6')-(2',3',4'-tri-O-acetyl-β-methyl-1'-thio-D-glucopyranoside) 
• 916494-82-1 rozavin hexaacetate 
• 866325-74-8 cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside 

Downstream Products

• 4510-34-3 (Z)-cinnamyl alcohol 
• 21040-45-9 Cinnamyl acetate 
• 916494-82-1 rozavin hexaacetate 
• 87-72-9 L-(+)-arabinose 
• 34047-83-1 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-((Z)-3-phenyl-allyloxy)-tetrahydro-pyran-3,4,5-triol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Relevant articles and documents

Synthetic method of rosavin

The present invention provides a synthetic method of rosavin. The method comprises the following steps: in a protective atmosphere and under presence of a water-removing agent, trimethylsilyl trifluoromethanesulfonate catalyzes 2,3,4-tri-O-acetyl-L-arabinofuranoside trichloroacetimide ester and ethyl 2,3,4-tri-O-acetyl-beta-D-thioglucopyranoside to react in an organic solvent, then beta-(E)-cinnamyl alcohol, NIS and TfOH are added in sequence to continue the reaction to completion, a reaction quencher is added, a crude intermediate is obtained by isolation, and then the crude intermediate reacts with sodium methoxide in methanol to separate and purify the rosavin. Commercial L-arabinose donor, D-glucose acceptor and beta-(E)-cinnamyl alcohol are used as raw materials to obtain a high-purity rosavin product through a three-step reaction, the intermediate does not need to be purified and a final product is obtained through crystallization with a total yield of 70% or more. The method isclean in reaction system, the product can be directly crystallized and separated from the system, the product has high yield and high purity, and the method is beneficial to large-scale industrializedpreparation of the rosavin.

Synthesis of Rosavin and its analogues based on a Mizoroki-Heck type reaction

The Rosavin framework could be constructed with either phenylboronic acids, the protected arabinopyranosyl bromide 4 or the protected xylopyranosyl bromide 5, along with allyl O-β-d-glucopyranoside 7 that could be easily prepared based on direct β-glucosidation between allyl alcohol and d-glucose using the immobilized β-glucosidase (EC 3.2.1.21). The key reaction was the Pd(II)-catalyzed Mizoroki-Heck type reaction between allyl β-d- glucopyranoside congeners 9 or 10 and arylboronic acids. Deprotection of the coupling products afforded synthetic Rosavin 1, 4-methoxycinnamyl 6-O-(α-l-arabinopyranosyl)-β-d-glucopyranoside 2, and cinnamyl 6-O-(β-d-xylopyranosyl)-β-d-glucopyranoside 3, which were identical with the natural products in respect to the specific rotation and spectral data.