24144-92-1

Basic information

• Product Name: TMS
• Synonyms: (E)-2,3',4,5'-TETRAMETHOXYSTILBENE;2,3',4,5'-TETRAMETHOXYSTILBENE;1-[(1E)-2-(3,5-DIMETHOXYPHENYL)ETHENYL]-2,4-DIMETHOXY-BENZENE;1-[2,(3,5-DIMETHOXYPHENYL)ETHENYL]-2,4-DIMETHOXYBENZENE;3,5,2’,4’-Tetramethoxystilbene;Benzene, 1-[(1E)-2-(3,5-diMethoxyphenyl)ethenyl]-2,4-diMethoxy-;(E)-1-(3,5-Dimethoxystyryl)-2,4-dimethoxybenzene;TMS, >=98%
• CAS NO: 24144-92-1
• Molecular Formula: C₁₈H₂₀O₄
• Molecular Weight: 300.35
• Product Categories: Antitumour
• Mol File: 24144-92-1.mol
• Article Data: 17

Chemical Properties

• Melting Point: 78-79 °C
• Boiling Point: 459.9 °C at 760 mmHg
• Flash Point: 152.3 °C
• Appearance: /
• Density: 1.117g/cm³
• Storage Temp.: Store at RT
• CAS DataBase Reference: TMS(CAS DataBase Reference)
• NIST Chemistry Reference: TMS(24144-92-1)
• EPA Substance Registry System: TMS(24144-92-1)

Safety Data

• Hazardous Substances Data: 24144-92-1(Hazardous Substances Data)

Usage

Chemical Description

TMS and TBS are silyl protecting groups used in organic synthesis.

Chemical Description

TMS (tetramethylsilane) is a volatile liquid used as an internal standard in NMR spectroscopy.

Chemical Description

TMS (trimethylsilyl) is used to cap the hydroxyl groups on the oligomers.

Chemical Description

TMS is a reference compound used in NMR spectroscopy to calibrate chemical shifts.

Chemical Description

TMS is short for tetramethylsilane, which is used as an internal reference in NMR spectroscopy.

Description

TMS, also known as 2,4,3',5'-Tetramethoxystilbene, is a potent and selective inhibitor of human cytochrome P450 1B1 (CYP1B1). It has been observed to inhibit cell growth and induce apoptosis in cancer cells. TMS is characterized by its ability to differentiate between various CYP450 families and its effectiveness in cultured human colon cancer cells.

Uses

Used in Pharmaceutical Industry:
TMS is used as an inhibitor for CYP1B1, which is an extrahepatic enzyme that oxidatively metabolizes both endogenous compounds (such as steroids and eicosanoids) and exogenous xenobiotics like polyaromatic hydrocarbons. Its high selectivity for CYP1B1 (50-fold over CYP1A1) makes it a valuable tool for differentiating between various CYP450 families.
Used in Cancer Treatment:
TMS is used as an anticancer agent, particularly in the treatment of human colon cancer cells. It has been shown to induce apoptosis and inhibit cell growth with an IC50 of 0.8 μg/ml, making it a promising candidate for cancer therapy.
Used in Drug Development and Research:
TMS serves as a useful tool in drug development and research, as it helps in understanding the role of CYP1B1 in various biological processes and its potential as a therapeutic target. Its ability to selectively inhibit CYP1B1 can aid in the design and development of new drugs targeting this enzyme.

Biological Activity

Potent, selective and competitive inhibitor of cytochrome P450 1B1, an enzyme overexpressed in certain tumors (IC 50 = 6 nM). 50- and 520-fold selective over P450 1A1 and 1A2 respectively. Inhibits cancer cell growth in vitro .

Upstream product

• 93340-42-2 (E)-3-(2,4-Dimethoxy-phenyl)-acrylic acid 3,5-dimethoxy-phenyl ester 
• 4721-07-7 oxyresveratrol 
• 74-88-4 methyl iodide 
• 6652-32-0 3,5-dimethoxybenzylchloride 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 20578-92-1 (E)-3,5,2',4'-tetramethoxystilbene 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 745026-69-1 ethyl 4-bromo-3,5-dimethoxybenzoate 
• 24082-46-0 2,4,3',5'-tetramethoxy-deoxybenzoin 
• 25245-27-6 1-iodo-3,5-dimethoxybenzene 

Downstream Products

• 4721-07-7 oxyresveratrol 
• 24131-34-8 2,4,3',5'-tetramethoxy-bibenzyl 
• 20578-92-1 (Z)-2,3',4,5'-tetramethoxystilbene 

Relevant articles and documents

Antiproliferative activity of stilbene derivatives and other constituents from the stem bark of Morus nigra L

The antiproliferative activities of 2′,3,4′,5,5′-pentahydroxy-cis-stilbene 1, resveratrol 2, oxyresveratrol 3, norartocarpetin 4, kuwanon C 5, morusin 6, cudraflavone A7, kuwanon G 8, albafuran C 9, mulberrofuran G 10, 3-acetyl-O-α-amyrin 11, 3-acetyl-O-β

Total synthesis of (±)-kuwanol e

The total synthesis of the Diels-Alder-type adducts (±)-kuwanol E and the heptamethyl ether derivative of (±)-kuwanon Y has been accomplished via a convergent strategy involving 2′-hydroxychalcone 6 or 9 and dehydroprenylstilbene 7, in nine steps. The syn

Oxyresveratrol: Structural modification and evaluation of biological activities

Oxyresveratrol (2,4,3' ,5' -tetrahydroxystilbene, 1), a phytoalexin present in large amounts in the heartwood of Artocarpus lacucha Buch.-Ham., has been reported to possess a wide variety of biological activities. As part of our continuing studies on the structural modification of oxyresveratrol, a library of twenty-six compounds was prepared via O-alkylation, aromatic halogenation, and electrophilic aromatic substitution. The two aromatic rings of the stilbene system of 1 can be chemically modulated by exploiting different protecting groups. Such a strategy allows for selective and exclusive modifications on either ring A or ring B. All compounds were evaluated in vitro for a panel of biological activities, including free radical scavenging activity, DNA protective properties, antiherpetic activity, inhibition of α-glucosidase and neuraminidase, and cytotoxicity against some cancer cell lines. Several derivatives were comparably active or even more potent than the parent oxyresveratrol and/or the appropriate positive controls. The partially etherified analogs 5' -hydroxy-2,3' ,4-trimethoxystilbene and 3' ,5' -dihydroxy-2,4-dimethoxystilbene demonstrated promising anti-herpetic and DNA protective activities, offering new leads for neuropreventive agent research, whereas 5' -hydroxy-2,3' ,4,-triisopropoxystilbene displayed anti-α-glucosidase effects, providing a new lead molecule for anti-diabetic drug development. 3' ,5' -Diacetoxy-2,4-diisopropoxystilbene showed potent and selective cytotoxicity against HeLa cancer cells, but the compound still needs further in vivo investigation to verify its anticancer potential.