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

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

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

• 192710-87-5 (E)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene 
• 587870-72-2 cis-3,5-diisopropoxy-4'-methoxystilbene 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 74-88-4 methyl iodide 
• 26153-38-8 3,5-dihydroxybenzaldehyde 
• 1530-38-7 ((4-methoxyphenyl)methyl)triphenylphosphonium bromide 
• 187803-40-3 3,5-bis(tert-butyldimethylsilyloxy)benzaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 192710-88-6 (Z)-3,5-di-(tert-butyldimethylsilyloxy)-4'-methoxystilbene 
• 104-01-8 4-Methoxyphenylacetic acid 
• 94169-64-9 3,5-diisopropyloxyphenylcarboxaldehyde 
• 587870-62-0 α-(4-methoxyphenyl)-m,m-diisopropoxycinnamic acid 
• 3462-97-3 (4-methoxybenzyl)triphenylphosphonium bromide 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 90332-29-9 α,β-dihydro-3,5-dihydroxy-4'-methoxystilbene 
• 197440-96-3 (E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene 
• 192710-95-5 (E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene 
• 14310-21-5 1-(4-methoxyphenyl)-2-phenylethane 
• 42206-94-0 triacetyl-trans-resveratrol 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 1428522-15-9 C₂₉H₂₀N₂O₉ 

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

Resveratrol derivative or medical application thereof in fibrosis resistance

The invention relates to an application of a resveratrol derivative as shown in a formula I or pharmaceutically acceptable salt thereof in preparation of drugs for treating fibrosis diseases. In the structural formula I, R1 is hydrogen atom or C1-C4 alkyl

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.

Method for synthesizing artificially all-trans-resveratrol and derivative thereof

The invention discloses a method for synthesizing artificially all-trans-resveratrol and a derivative thereof. In the method, the precursors of all-trans-resveratrol and the derivative thereof are prepared by means of constructing a conjugated fused ring, thus the all-trans-spatial structure of resveratrol and the derivative thereof is restricted completely, to prepare all-trans-resveratrol and the derivative thereof. The resulting product of the preparation method of 1,2-stilbene or the derivative thereof in the invention is of all-trans configuration, so as to meet the demand of biologically active substance chemicals. Compared to the previous processes, the method provided by the invention has the advantages of simple processes and mild conditions, thereby meeting the green chemistry concept.

Synthesis of resveratrol derivatives as new analgesic drugs through desensitization of the TRPA1 receptor

A series of 31 resveratrol derivatives was designed, synthesized and evaluated for activation and inhibition of the TRPA1 channel. Most acted as activators and desensitizers of TRPA1 channels like resveratrol or allyl isothiocyanate (AITC). Compound 4z (HUHS029) exhibited higher inhibitory activity than resveratrol with an IC50 value of 16.1?μM. The activity of 4z on TRPA1 was confirmed in TRPA1-expressing HEK293 cells, as well as in rat dorsal root ganglia neurons by a whole cell patch clamp recording. Furthermore, pretreatment with 4z exhibited an analgesic effect on AITC-evoked TRPA1-related pain behavior in vivo.

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.

Alkyl derivative manufacturing method

PROBLEM TO BE SOLVED: To provide a new method for producing an alkyl derivative of a polyphenol. SOLUTION: The method for producing an alkyl derivative of a polyphenol includes a step of reacting an acetic acid salt and an alkylating agent with the polyphenol. COPYRIGHT: (C)2013,JPOandINPIT

Antifungal activity of resveratrol derivatives against Candida Species

trans-Resveratrol (1a) is a phytoalexin produced by plants in response to infections by pathogens. Its potential activity against clinically relevant opportunistic fungal pathogens has previously been poorly investigated. Evaluated herein are the candidacidal activities of oligomers (2a, 3-5) of 1a purified from Vitis vinifera grape canes and several analogues (1b-1j) of 1a obtained through semisynthesis using methylation and acetylation. Moreover, trans-ε-viniferin (2a), a dimer of 1a, was also subjected to methylation (2b) and acetylation (2c) under nonselective conditions. Neither the natural oligomers of 1a (2a, 3-5) nor the derivatives of 2a were active against Candida albicans SC5314. However, the dimethoxy resveratrol derivatives 1d and 1e exhibited antifungal activity against C. albicans with minimum inhibitory concentration (MIC) values of 29-37 μg/mL and against 11 other Candida species. Compound 1e inhibited the yeast-to-hyphae morphogenetic transition of C. albicans at 14 μg/mL.

Unexpected O-alkylation and ester migration in phenolic 2,3-diaryl-2,3-dihydrobenzo[b]furans

O-alkylation of 2-(4-methoxyphenyl)-5-hydroxy-3-[1,3-phenylene-bis(4- nitrobenzoate)]-2,3-dihydrobenzo[b]furan results in the unexpected hydrolysis of the nitrobenzoate esters, transfer of a 4-nitrobenzoic acid group to the 5-hydroxyl group and double alkylation of the newly formed 3,5-diphenol moiety. A range of alkyl halides can be used and give access to O-alkyl analogues of -viniferin.

Heck arylation of styrenes promoted by an air-stable phosphinito complex with palladium(II); Synthesis of resveratrol

An air-stable phosphinito complex of palladium(II) was found to be an efficient catalyst in the Heck reaction of a variety of aryl halides and styrenes. Resveratrol was concisely synthesized in 63% overall yield; the reactions were performed under conventional and microwave heating. Georg Thieme Verlag Stuttgart New York.