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22255-22-7

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22255-22-7 Usage

Description

trans-trismethoxy Resveratrol is a polyketide synthase-derived stilbene originally isolated from Virola cuspidata that has diverse biological activities. It is cytotoxic to several cancer cell lines, including PC3, KB, HT-29, SW480, and HL-60 cells (IC50s =3.6, 10.2, 16.1, 54, and 2.5 μM, respectively). trans-trismethoxy Resveratrol (15 μM) inhibits TNF-α-induced activation of NF-κB in HEK293T cells in a reporter assay. It inhibits angiogenesis in zebrafish embryos when used at a concentration of 0.1 μM.

Chemical Properties

Pale Yellow Oil

Uses

Different sources of media describe the Uses of 22255-22-7 differently. You can refer to the following data:
1. A resveratrol analog with a variety of pharmacology action, including anti-cancer properties, anti-allergic activity, estrogenic activity, antiangiogenic activity, and vascular-targeting activity against microtubule-destabilization
2. A resveratrol analog with a variety of pharmacology action, including inst microtubule-destabilization
3. Phenolic compounds, particularly flavonoids, from plant sources have long been observed to have antioxidant activity with potential benefits for human health. Resveratrol is a potent phenolic antioxidant found in grapes and red wine that also has antiproliferative and anti-inflammatory activity. When the three phenolic hydroxyl groups of resveratrol are converted to methyl ethers, the inhibition of cell growth and pro-apoptotic activities of resveratrol are enhanced.

Check Digit Verification of cas no

The CAS Registry Mumber 22255-22-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,2,5 and 5 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 22255-22:
(7*2)+(6*2)+(5*2)+(4*5)+(3*5)+(2*2)+(1*2)=77
77 % 10 = 7
So 22255-22-7 is a valid CAS Registry Number.
InChI:InChI=1/C17H18O3/c1-18-15-8-6-13(7-9-15)4-5-14-10-16(19-2)12-17(11-14)20-3/h4-12H,1-3H3/b5-4+

22255-22-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • TCI America

  • (T1829)  3,4',5-Trimethoxy-trans-stilbene  >98.0%(GC)

  • 22255-22-7

  • 5g

  • 2,990.00CNY

  • Detail
  • Sigma

  • (SML0051)  E-Resveratrol Trimethyl Ether  ≥98% (HPLC)

  • 22255-22-7

  • SML0051-10MG

  • 389.61CNY

  • Detail
  • Sigma

  • (SML0051)  E-Resveratrol Trimethyl Ether  ≥98% (HPLC)

  • 22255-22-7

  • SML0051-50MG

  • 1,606.41CNY

  • Detail

22255-22-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-dimethoxy-5-[(E)-2-(4-methoxyphenyl)ethenyl]benzene

1.2 Other means of identification

Product number -
Other names O-permethylated E-resveratrol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22255-22-7 SDS

22255-22-7Relevant articles and documents

Complete assignment of the1H and13C NMR spectra of resveratrol derivatives

Koh, Dongsoo,Park, Kwan Ha,Jung, Jihyun,Yang, Heejung,Hun Mok,Lim, Yoongho

, p. 768 - 770 (2001)

Contract/grant sponsor: Korea Ministry of Marine Affairs and Fishery The complete 1H and 13C chemical shift assignments of six derivatives of resveratrol [(E)-5-[2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol] that possess leukotriene D

Heterogeneous heck coupling in multivariate metal-organic frameworks for enhanced selectivity

Brown, Jonathan W.,Jarenwattananon, Nanette N.,Otto, Trenton,Wang, James L.,Gl?ggler, Stefan,Bouchard, Louis-S.

, p. 105 - 107 (2015)

Abstract Highly selective heterogeneous Heck coupling has been demonstrated inside a series of metal-organic frameworks (MOFs). These MOFs, Zn4O(BDC-NH2)n(BDC)(3 - n) (n = 3, 2.4, 1.8, 1.2, 0.9, 0.75, 0.6, 0.3,

Novel resveratrol-based flavonol derivatives: Synthesis and anti-inflammatory activity in vitro and in vivo

Chen, Liu Zeng,Yao, Li,Jiao, Ming Ming,Shi, Jing Bo,Tan, Yue,Ruan, Ban Feng,Liu, Xin Hua

, p. 114 - 128 (2019)

In order to discover novel anti-inflammatory agents, total thirty-seven new resveratrol-based flavonol derivatives were designed and synthesized. All compounds have been screened for their anti-inflammatory activity by evaluating their inhibition effect of LPS-induced NO production in RAW 264.7 macrophages. Their toxicity was also assessed in vitro. Structure-activity relationships (SARs)have been concluded, and finally 2-(2,4-dimethoxy-6-(4-methoxystyryl)phenyl)-3-hydroxy-4H-chromen-4-one was found to be the most active scaffold with low toxicity. This compound could significantly decrease productions of NO, IL-6 and TNF-α with IC50 values of 1.35, 1.12 and 1.92 μM, respectively in RAW 264.7 macrophages. Preliminary mechanism studies indicated that it could inhibit the expression of TLR4 protein, resulting in activation of the NF-?B cell signaling pathway. The in vivo anti-inflammatory activity of this compound could reduce pulmonary inflammation by mouse model of LPS-induced acute lung injury (ALI). We believe these findings would further support studies of rational design of more efficient acute lung injury regulatory inhibitors.

Jiewei, Tian,Lei, Wang,Xiufeng, Long,Heming, Zhang,Xiaoguang, Li,Haiyan, Fu,Yongqiang, Tian

, p. 2343 - 2346 (2018)

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Ingham,J.L.

, p. 1791 - 1793 (1976)

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An expedient synthesis of resveratrol through a highly recoverable palladium catalyst

Martínez, Alejandro V.,García, José I.,Mayoral, José A.

, p. 5581 - 5584 (2017)

A straightforward two-step synthesis of resveratrol is described, with total isolated yields in the range of 75–80%. The key synthetic step, a Heck–Mizoroki C[sbnd]C cross-coupling reaction, is efficiently promoted by a heterogeneous catalyst consisting of palladium nanoparticles supported on synthetic clay. This solid catalyst is quite handy and displays high stability and robustness under reaction conditions. The catalyst can be easily recovered and reused at least 10 times, which improves the overall catalytic efficiency of the system. Moreover, the use of solvents is limited, and the reaction procedure allows a facile separation and purification of the desired product, free from the concomitant ionic by-product and from palladium contamination.

Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis

Babu, Reshma,Balaraman, Ekambaram,Midya, Siba P.,Subaramanian, Murugan,Yadav, Vinita

, p. 7552 - 7562 (2021/06/28)

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

Non-Chelate-Assisted Palladium-Catalyzed Aerobic Oxidative Heck Reaction of Fluorobenzenes and Other Arenes: When Does the C?H Activation Need Help?

Albéniz, Ana C.,Villalba, Francisco

supporting information, p. 4795 - 4804 (2021/09/06)

The pyridone fragment in the ligand [2, 2’-bipyridin]-6(1H)-one (bipy-6-OH) enables the oxidative Heck reaction of simple arenes with oxygen as the sole oxidant and no redox mediator. Arenes with either electron-donating or electron-withdrawing groups can be functionalized in this way. Experimental data on the reaction with toluene as the model arene shows that the C?H activation step is turnover limiting and that the ligand structure is crucial to facilitate the reaction, which supports the involvement of the pyridone fragment in the C?H activation step. In the case of fluoroarenes, the alkenylation of mono and 1,2-difluoro benzenes requires the presence of bipy-6-OH. In contrast, this ligand is detrimental for the alkenylation of 1,3-difluoro, tri, tetra and pentafluoro benzenes which can be carried out using just [Pd(OAc)2]. This correlates with the acidity of the fluoroarenes, the most acidic undergoing easier C?H activation so other steps of the reaction such as the coordination-insertion of the olefin become kinetically important for polyfluorinated arenes. The use of just a catalytic amount of sodium molybdate as a base proved to be optimal in all these reactions. (Figure presented.).

A Simple Nickel Catalyst Enabling an E-Selective Alkyne Semihydrogenation

Thiel, Niklas O.,Kaewmee, Benyapa,Tran Ngoc, Trung,Teichert, Johannes F.

, p. 1597 - 1603 (2020/02/05)

Stereoselective alkyne semihydrogenations are attractive approaches to alkenes, which are key building blocks for synthesis. With regards to the most atom-economic reducing agent dihydrogen (H2), only few catalysts for the challenging E-selective alkyne semihydrogenation have been disclosed, each with a unique substrate scope profile. Here, we show that a commercially available nickel catalyst facilitates the E-selective alkyne semihydrogenation of a wide variety of substituted internal alkynes. This results in a simple and broadly applicable overall protocol to stereoselectively access E-alkenes employing H2, which could serve as a general method for synthesis.

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