50450-35-6

Basic information

• Product Name: trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside
• CAS NO: 50450-35-6
• Molecular Weight: 418.444
• Mol File: 50450-35-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside(50450-35-6)
• EPA Substance Registry System: trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside(50450-35-6)

Safety Data

• Hazardous Substances Data: 50450-35-6(Hazardous Substances Data)

Usage

General Description

Trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside is a chemical compound that belongs to the stilbene group, which is a derivative of resveratrol. It is commonly found in plants such as Rheum undulatum and is known for its potential medicinal properties, including antioxidant, anti-inflammatory, and anti-cancer effects. The compound has been studied for its ability to inhibit the growth of cancer cells and reduce inflammation in various disease conditions. Additionally, it has been investigated for its potential in preventing and treating cardiovascular diseases and neurodegenerative disorders. Trans-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside has shown promise in various preclinical studies and is considered a valuable compound for further research and development in the field of medicine and pharmacology.

Upstream product

• 537-42-8 3,5-dimethoxy-4'-hydroxy-trans-stilbene 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 58762-96-2 3,4'-dihydroxy-5-methoxy-trans-stilbene 4'-O-β-D-glucopyranoside 
• 74-88-4 methyl iodide 
• 38963-95-0 trans-resveratroloside 
• 952585-00-1 uridine-5'-diphosphoglucose 

Downstream Products

• 1367298-00-7 trans-2,6-dichloro-3,5-dimethoxystilbene-4'-O-β-D-glucopyranoside 
• 1367298-01-8 trans-2,6-dichloro-3,5-dimethoxystilbene-4'-O-β-D-glucuronide 

Relevant articles and documents

Alkylated resveratrol prodrugs and metabolites as potential therapeutics for neurodegenerative diseases

Resveratrol is a naturally occurring stilbene which has shown promising results as treatment for several neurodegenerative diseases. However, its application is limited due to its low efficacy and bioavailability. Here, we have designed and synthesized alkylated resveratrol prodrugs combining structural modification to improve antioxidant and anti-inflammatory properties and the preparation of prodrugs to extend drug bioavailability. For comparison we also studied resveratrol prodrugs and alkylated resveratrol derivatives. Methylated and butylated resveratrol derivatives showed the best in vitro neuroprotective and anti-inflammatory activity. The glucosyl- and glucosyl-acyl- prodrugs of these derivatives showed lower toxicity on zebra fish embryo. When neuroprotection was examined on pentylenetetrazole challenged zebra fish, they were capable of reverting neuronal damage but to a lower extent than resveratrol. Nevertheless, 3-O-(6′-O-octanoyl)-β-D-glucopyranoside resveratrol (compound 8) recovered AChE activity over 100% whereas resveratrol only up to 92%. In a 3-nitropropionic acid mice model of Huntington's disease, resveratrol derivative 8 delayed the onset and reduced the severity of HD-like symptoms, by improving locomotor activity and protecting against weight loss. Its effects involved an equal antioxidant but better anti-inflammatory profile than resveratrol as shown by SOD2 expression in brain tissue and circulating levels of IL-6 (11 vs 18 pg/mL), respectively. Finally, the octanoyl chain in compound 8 could be playing a role in inflammation and neuronal development indicating it could be acting as a double-drug, instead of as a prodrug.

Reaction of several resveratrol glycoside derivatives with hypochlorites in various media

The reactions of pterostilbenoside (trans-3,5-dimethoxystilben-4′-O- β-D-glucoside) and Ar-O-Tr derivatives of resveratroloside (3,5-dihydroxystilben-4′-O-β-D-glucoside) and pinostilbenoside (3-methoxy-5-hydroxystilben-4′-O-β-D-glucoside) with NaOCl and t-BuOCl in the presence of the stable nitroxyl radical TEMPO were studied in various media. It was found that the principal product of pterostilbenoside transformation was its 2,6-dichloroderivative, a part of which was oxidized to form 2,6-dichloropterostilbene glucuronide. Trityl ethers of resveratroloside and pinostilbenoside reacted with the hypochlorites to form mixtures of products.