33626-08-3

Basic information

• Product Name: 4'-Methoxyresveratrol
• Synonyms: 4'-Methoxyresveratrol;(E)-3,5-Dihydroxy-4'-methoxystilbene;4'-Methoxy resveratol;(E)-5-(4-Methoxystyryl)benzene-1,3-diol;4'-O-Methylresveratrol;Desoxyrhapontigenin;-5-(4-Methoxystyryl)
• CAS NO: 33626-08-3
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.273
• EINECS: 1312995-182-4
• Mol File: 33626-08-3.mol
• Article Data: 25

Chemical Properties

• Melting Point: 158-166 °C
• Boiling Point: 446.5±14.0 °C(Predicted)
• Appearance: /
• Density: 1.252
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.19±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 4'-Methoxyresveratrol(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Methoxyresveratrol(33626-08-3)
• EPA Substance Registry System: 4'-Methoxyresveratrol(33626-08-3)

Safety Data

• Hazardous Substances Data: 33626-08-3(Hazardous Substances Data)

Usage

Description

4'-Methoxyresveratrol, also known as 4'-O-Methylresveratrol, is a white crystalline powder that serves as an impurity of resveratrol (R150000). It is a naturally occurring compound with potential pharmaceutical applications due to its bioactive properties.

Uses

Used in Anticancer Applications:
4'-Methoxyresveratrol is used as an anticancer agent for its ability to inhibit events associated with tumor initiation, promotion, and progression. It contributes to the overall effectiveness of resveratrol, a well-known compound with cancer-fighting properties.
Used in Pharmaceutical Industry:
4'-Methoxyresveratrol is used as a compound of interest in the pharmaceutical industry for its potential to be developed into a therapeutic agent targeting various types of cancer. Its presence as an impurity in resveratrol suggests that it may have synergistic effects when combined with other anticancer agents, enhancing their efficacy and potentially leading to novel treatment strategies.

Upstream product

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 74-88-4 methyl iodide 
• 192710-88-6 (Z)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene 
• 1963-36-6 4-methoxycinnamaldehyde 
• 62378-72-7 6-(4-methoxyphenyl)-3,5-hexadiene-2-one 
• 637-69-4 4-Methoxystyrene 
• 39192-49-9 3,5-diacetoxybenzoyl chloride 
• 33620-66-5 Desoxy-rhapontigenin-diacetat 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 103929-84-6 [3,5-di(tert-butyldimethylsilanyloxy)phenyl]methanol 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 103929-83-5 methyl 3,5-bis(tert-butyldimethylsilyloxy)benzoate 
• 108-73-6 3,5-dihydroxyphenol 
• 64339-43-1 5-iodoresorcinol 

Downstream Products

• 1428522-15-9 C₂₉H₂₀N₂O₉ 
• 192710-95-5 (E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 42206-94-0 triacetyl-trans-resveratrol 
• 30197-14-9 (E)-3-(β-D-glucopyranosyloxy)-5-hydroxy-4'-methoxystilbene 
• 27208-80-6 polydatin 

Relevant articles and documents

Design, synthesis and biological evaluation of resveratrol-cinnamoyl derivates as tubulin polymerization inhibitors targeting the colchicine binding site

A novel series of resveratrol-cinnamoyl hybrids as tubulin polymerization inhibitors were designed and synthesized, and evaluated for their anti-proliferative activities against A549, MCF-7, HepG2, HeLa and MDA-MB-231 five cancer cell lines. Most designed

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.

Dehydrogenative Formation of Resorcinol Derivatives Using Pd/C-Ethylene Catalytic System

The conversion of substituted 1,3-cyclohexanediones to the alkyl ethers of resorcinol using a Pd/C-ethylene system is reported. In these reactions, ethylene works as a hydrogen acceptor. The efficient synthesis of resveratrol was achieved using this protocol as a key step. In addition, the direct formation of substituted resorcinols was carried out by adding K2CO3 into the reaction media.