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3,4',5-Trimethoxy-trans-stilbene (TMTS) is a chemical substance belonging to the Stilbene class of compounds. Molecular formula: C18H20O3, CAS 22255-22-7, molecular weight: 284.35 g/mol. It is a solid, commonly in the form of white crystalline powder or crystal. It is an important photosensitive compound with certain luminescent properties. It can absorb ultraviolet and visible light in the area and emit visible light. Its optical properties make it useful in fields such as chemiluminescence and optoelectronics. The infrared spectrum of TMTS can provide information about its molecular structure and functional groups. Typically, characteristic peaks such as benzene ring and ether group are displayed. It is a multifunctional compound with extensive applications in fields such as chemiluminescence, photosensitive materials, optoelectronic devices, chemical synthesis, antibacterial, and antioxidant properties. Its unique properties make TMTS significant in fields such as scientific research, medicine, materials science, and environmental protection.
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Chemical Formula |
C17H18O3 |
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Exact Mass |
270 |
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Molecular Weight |
270 |
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m/z |
270 (100.0%), 271 (18.4%), 272 (1.6%) |
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Elemental Analysis |
C, 75.53; H, 6.71; O, 17.76 |
Chemiluminant:
TMTS is an important chemiluminescent agent that can generate visible light by stimulating luminescence. This chemiluminescence reaction typically involves the reaction of TMTS with oxidants such as oxygen or hydrogen peroxide. The chemiluminescence properties of TMTS have made it widely used in fields such as biomedical research, biological analysis, and ecology. For example, in biosensors, TMTS can be used as a probe to detect the presence and activity of biological molecules.
Photosensitive materials:
TMTS, as a compound with photosensitive properties, can be used to prepare photosensitive materials. Photosensitive materials refer to materials that undergo significant physical or chemical changes under light stimulation. TMTS can be used as monomers or additives for photosensitive polymers, and photosensitive polymer materials can be prepared through photoinduced polymerization reactions. These materials have applications in optical recording, photolithography and Photonics.
Optoelectronic devices:
TMTS has excellent optoelectronic properties, making it an ideal material for preparing optoelectronic devices. For example, TMTS can be used to prepare optoelectronic converter devices, photodiodes, organic light emitting diodes (OLEDs), and organic thin film solar cells. As a charge transfer material or light absorption layer, TMTS can improve the performance of devices and enhance Solar-cell efficiency.
Chemical synthesis intermediates:
TMTS is an important chemical synthesis intermediate that can be used to synthesize other organic compounds. Its ether based structure allows TMTS to undergo various functional group modifications and functionalization reactions, resulting in the synthesis of diverse compounds. TMTS can be used as reaction substrate, catalyst or ligand in the organic synthesis process, such as the synthesis of synthetic drugs, Natural product and material chemistry.
Antibacterial agents:
TMTS has certain antibacterial activity and can be used to develop antibacterial agents and preservatives. Research has shown that TMTS has inhibitory effects on the growth of certain bacteria and fungi. This makes TMTS have potential application prospects in the pharmaceutical and food industries. Its antibacterial properties can also be used to prepare antibacterial coatings, medical devices, and packaging materials.
Antioxidants:
TMTS has antioxidant properties and can be used as an antioxidant in food, cosmetics, and health products. Antioxidants can help protect cells from free radical damage and prevent oxidative stress and aging issues. TMTS can provide antioxidant protection by clearing free radicals or reducing oxidation reactions.
Fluorescent probe:
TMTS has excellent fluorescence properties and can be used as a fluorescence probe to detect and analyze biomolecules or environmental pollutants. By modifying the structure of TMTS or combining with other molecules, selective detection and sensing of specific target substances can be achieved. This makes TMTS widely applicable in biomedical research, environmental monitoring, and biological analysis.
There are various pathways for the laboratory synthesis of 3,4',5-Trimethoxy-trans-stilbene (TMTS).
Synthesis method 1:
TMTS can be synthesized through two steps: lithium bromide alkylation reaction and Wittig reaction. The specific steps are as follows:
P-methoxybenzylbromide (p-neneneba methoxy benzyl bromide) is reacted with propyl lithium to form p-methoxybenzyl lithium (p-methoxybenzyllithium) intermediate.
Chemical equation:
C8H9OBr+C3H7Li → C8H9OLi+C3H7Br
The p-methoxybenzyl lithium obtained in the previous step was subjected to Wittig reaction with the corresponding aromatic aldehyde to generate the target product 3,4 ', 5-TRIMETHOXY-TRANS-STILBENE (TMTS).
Chemical equation:
C8H9OLi+Ph CHO → Ph CH=C (Ph) - OCH3+LiOH
Comprehensive Chemical equation:
C8H9OBr+C3H7Li+Ph CHO → Ph CH=C (Ph) - OCH3+C3H7Br+LiOH
This is a common method for synthesizing TMTS, but there are other methods available for synthesizing TMTS. The specific experimental conditions and reaction temperature need to be determined based on the specific situation to ensure the efficiency and selectivity of the synthesis reaction.
Synthesis Method 2:
The following is another method of synthesizing TMTS in the laboratory and the corresponding Chemical equation:
Benzoic acid and formaldehyde react under acidic conditions to produce methyl benzylate.
Chemical equation:
C6H5COOH+CH2O → C6H5CH2COOCH3+H2O
Benzoic acid is obtained by heating the methyl ester of benzyl formate or hydrolyzing it with NaOH solution.
Chemical equation:
C6H5CH2COOC2H5+NaOH → C6H5CH2COOH+C2H5OH
Benzoic acid is reacted with Sodium bisulfite (NaHSO3) or Sodium hypochlorite (NaClO) to produce styrene dimethyl ether.
Chemical equation:
C6H5CH2COOH+NaHSO3 → C6H5CH=CH2+NaHSO4+H2O
or
C6H5CH2COOH+NaClO → C6H5CH=CH2+NaCl+H2O
Styrene dimethyl ether is reacted with sodium hydroxide (NaOH) in alcohol solvent to obtain 3,4 ', 5-TRIMETHOXY-TRANS-STILBENE through decarboxylation and Isomerization.
Chemical equation:
C6H5CH=CH2+2NaOH → C6H5CHOHCH2Na+H2O
C6H5CHOHCH2Na → C6H5CH=CH2+NaCHO+H2O
Comprehensive Chemical equation:
C6H5COOH+CH2O → C6H5CH2COOCH3+H2O
C6H5CH2COOCH3+NaOH → C6H5CH2COOH+CH3OH
C6H5CH2COOH+NaHSO3 → C6H5CH=CH2+NaHSO4+H2O
or
C6H5CH2COOH+NaClO → C6H5CH=CH2+NaCl+H2O
C6H5CH=CH2+2NaOH → C6H5CHOHCH2Na+H2O
C6H5CHOHCH2Na → C6H5CH=CH2+NaCHO+H2O
This method gradually synthesized 3,4',5-Trimethoxy-trans-stilbene (TMTS) by reacting benzoic acid and formaldehyde. It should be noted that during the experimental process, reaction conditions should be strictly controlled and appropriate solvents, reagents, and equipment should be used to ensure the safety and efficiency of the experiment.
why choose it
3,4 ', 5-trimethoxy-trans-diphenylethene is a chemical substance, with the English name 3,4', 5-TRIMETHOXY-TRANS-STILBENE and CAS number 22255-22-7. It is also known as resveratrol trimethyl ether.
In terms of chemical structure, this compound has a specific molecular formula and structural formula, and its molecular formula is C17H18O3. This compound has important applications in the field of fine chemicals and is widely used in various colleges, research institutions, and chemical enterprises, receiving praise from users.
In addition, 3,4 ', 5-trimethoxy-trans-diphenylethene also has some downstream products, such as resveratrol and 2,4,6-trimethoxyphenanthrene. These downstream products may have specific applications in their respective fields.
The development history of 3,4 ', 5-trimethoxy-transstilbene (CAS number 22255-22-7) can be traced back to the chemical modification research of resveratrol. Its development process reflects the scientific evolution from the exploration of natural product derivatives to the development of functional compounds, which can be divided into the following stages:
Resveratrol, as a natural polyphenolic compound found in plants such as grapes and peanuts, has attracted much attention for its antioxidant, anti-inflammatory, and anti-tumor activities. At the end of the 20th century and the beginning of the 21st century, researchers discovered that the stilbene core structure of resveratrol has the potential for chemical modification, and its biological activity can be optimized by introducing functional groups such as methoxy. This substance is the product of this idea: by methylating the hydroxyl group of resveratrol to form a fully methoxylated derivative, it aims to enhance its lipid solubility, metabolic stability, and targeting.
Early research focused on optimizing synthesis methods. For example, in 2011, a team from Central South University proposed using resveratrol as the raw material, which was dissolved in ethyl acetate, catalyzed by anhydrous potassium carbonate, and methylated with dimethyl sulfate. The reaction was carried out at 35-75 ℃ for 4-8 hours, and finally purified by ethanol recrystallization with a yield of 74.5%. This method avoids the difficulties in separating cis trans isomers and the high cost of column chromatography purification in traditional Wittig reactions, laying the foundation for industrial production.
Since 2008, synthetic technology has continued to improve. The researchers used metal catalytic methods such as Wittig Horner reaction, Corey Fuchs reaction, and Suzuki coupling, combined with low-temperature reaction control, to improve the purity of the product. For example, the team from Tianjin Normal University prepared its crystal through the Wittig Horner reaction and analyzed its triclinic structure, revealing the influence of intramolecular π - π stacking on stability.
Between 2012 and 2015, industrial synthesis technology matured. Multiple enterprises, such as Hubei Shixing Chemical and Nanjing Chunqiu Biology, have achieved kilogram level production using a two-step crystallization method of ethyl acetate/ethanol, with a purity of 99% and a cost reduction of 10-100 yuan per kilogram, meeting the demand for pharmaceutical intermediates.
In 2014, a study published in the Chinese Journal of Pharmacy confirmed that the compound has significant anti-inflammatory effects on a rat model of osteoarthritis. Its activity in inhibiting tumor necrosis factor alpha (TNF - α) and cyclooxygenase-2 (COX-2) is superior to that of the clinical drug diacerein. In 2020, a team from South China University of Technology discovered its antibacterial activity against gray mold, expanding its potential applications in the agricultural field.
Mechanism studies have revealed that methoxylation modification enhances the lipophilicity of molecules, promotes their penetration through cell membranes, and improves the binding efficiency with target proteins by stabilizing the trans conformation. Quantum chemistry calculations further confirm that the energy difference between the two conformations in its crystal structure is only 5.51 kJ/mol, ensuring the stability of its biological activity.
At present, 3,4',5-Trimethoxy-trans-stilbene has entered the pharmaceutical intermediate market as a leading compound in the development of anti-tumor and anti-inflammatory drugs. For example, Shanghai Aladdin Biochemical Technology Co., Ltd. provides 97% purity products for cell signaling research; Hubei Cuiyuan Biotechnology Co., Ltd. uses it as a standard and supplies it to global research institutions.
In the field of materials, its conjugated styrene structure is used to prepare luminescent materials and polymer additives. In 2018, a team from Tianjin University developed a derivative with aggregation induced luminescence (AIE) properties by introducing trifluoromethyl groups, which was applied in biological imaging.
Frequently Asked Questions
What is trihydroxy trans-stilbene?
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Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi.
What are the benefits of stilbenes?
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Natural antifungal, antibacterial, and antiviral compounds, stilbenes have also been shown to have anti-inflammatory properties, estrogen receptor agonist activities, and effects on cell proliferation, cell signaling pathways, and apoptosis [94,95]. trans-Stilbenes make up the majority of all-natural stilbenes.
What not to mix with resveratrol?
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Medications that slow blood clotting (Anticoagulant / Antiplatelet drugs) interacts with Resveratrol. Resveratrol might slow blood clotting. Taking resveratrol along with medications that also slow blood clotting might increase the risk of bruising and bleeding.
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