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3,4,5-trimethoxybenzaldehyde, usually appears as white to slightly yellow needle shaped crystals or powder. Molecular formula C10H12O4, CAS 86-81-7, has low solubility in water and exhibits slight solubility. But in organic solvents such as methanol, its solubility is relatively high, reaching 0.1 g/mL. This good solubility in organic solvents makes it easier to mix and react with other compounds in chemical reactions. It is a multifunctional organic compound with wide applications in fields such as medicine and chemical engineering. In the medical field, it is mainly used for synthesizing sulfonamide drugs, antimicrobial enhancers TMP, and drugs for treating bronchial asthma and asthmatic bronchitis. In the field of chemical engineering, it can be used as an intermediate for organic synthesis raw materials and dye pigment synthesis. In addition, it can also be used as a research reagent and pesticide intermediate.
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Chemical Formula |
C10H12O4 |
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Exact Mass |
196 |
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Molecular Weight |
196 |
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m/z |
196 (100.0%), 197 (10.8%) |
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Elemental Analysis |
C, 61.22; H, 6.17; O,32.62 |
3,4,5-trimethoxybenzaldehyd (CAS number: 86-81-7) is an organic compound with a unique molecular structure. Its benzene ring contains three methoxy groups (- OCH ∝) and one aldehyde group (- CHO), giving it high reactivity and wide application value. The compound appears as white to slightly yellow needle shaped crystals with a melting point range of 72-78 ℃. It is insoluble in water but easily soluble in organic solvents such as methanol and ethanol. Its chemical properties are stable, but it needs to be stored in a sealed manner away from light and moisture.
It is a key intermediate for synthesizing the antibacterial and synergistic drug trimethoprim (TMP). TMP inhibits bacterial dihydrofolate reductase, blocks bacterial nucleic acid synthesis, and can enhance antibacterial effects when combined with sulfonamide drugs. Its synthesis pathway involves multiple reactions:
Methylation and esterification: Using gallic acid or tannic acid as raw materials, methyl trimethoxybenzoate is generated by methylation with dimethyl sulfate, with a yield of up to 106-110%.
Hydrazine reaction: Methyl trimethoxybenzoate and hydrazine hydrate are refluxed at 90-95 ℃ for 3 hours to generate trimethoxybenzoyl hydrazine, with a melting point of 159-161 ℃.
Oxidation reaction: Trimethoxybenzoyl hydrazine reacts with hematite (potassium ferrocyanide) in an ammonia and toluene system to produce 3,4,5-trimethoxybenzaldehyde with a yield of 77-81%.
In addition, the compound can also be used for the synthesis of the anti anxiety drug trimethoxyline, the cough suppressant and expectorant drug Chuansu Ning, and the anti hypertensive drug Trasxifloxacin. For example, in the synthesis of quercetin, cinnamic acid ester derivatives are generated through condensation reactions to further optimize drug activity.
1. Spices and additives
Its aldehyde group can participate in the synthesis of various fragrances. For example:
Methyl trimethoxycinnamate: formed by condensation with dimethyl malonate, it has a compound aroma of woody and fruity, and is widely used in cosmetics and daily chemical products.
Trimethoxybenzoic acid: It is prepared by oxidation reaction and used for food essence preparation, giving the product sweet and floral fragrance.
2. Pesticide intermediates
This compound exhibits outstanding performance in pesticide synthesis. For example:
Dimethoxybenzoyl hydrazine: generated through hydrazine reaction, it is an intermediate of the insecticide fipronil and can effectively control Lepidoptera pests.
Brominated derivatives: 3,4,5-trimethoxybenzaldehyd undergoes bromination reaction to generate brominated products, which are further synthesized into herbicide active ingredients.
3. Dyes and pigments
Its methoxy structure can enhance the molecular conjugation system and improve the color fastness of dyes. For example:
Disperse dye: Condenses with azo compounds to form triazine dyes, suitable for dyeing polyester fibers.
Fluorescent whitening agent: By reacting with aniline compounds, a whitening agent with blue light effect is generated to enhance the whiteness of textiles.
1. Polymer materials
Its aldehyde group can participate in polymerization reactions to generate polymer materials with special propertes:
Polyester resin: It condenses with diols to form linear polyester, which is used in coatings and adhesives to enhance chemical resistance.
Crosslinking agent: Introducing this compound into epoxy resin can enhance the thermal stability and mechanical strength of the material.
2. Metal organic frameworks (MOFs)
Its methoxy and aldehyde groups can coordinate with metal ions to construct porous MOFs materials:
Gas adsorption: By coordinating with zinc and copper ions, MOFs with high specific surface area are generated for CO ₂ capture and hydrogen storage.
Catalytic carrier: After loading palladium nanoparticles, MOFs materials can efficiently catalyze olefin hydrogenation reactions.
3. Nanomaterials
Can be used as a surface modifier to regulate the morphology of nanoparticles:
Gold nanorods: By reacting aldehyde groups with gold precursors, controllable length gold nanorods are generated for photothermal therapy.
Quantum dots: Methoxy groups can stabilize surface defects of quantum dots, improve fluorescence efficiency, and be applied in biological imaging.
1. Biomedical applications
Antibacterial material: It ethanolamine Schiff base has an inhibition rate of over 90% against Escherichia coli and Staphylococcus aureus, and can be used for medical dressing coatings.
Antitumor drug: its derivatives can inhibit the proliferation of breast cancer cells by inducing tumor cell apoptosis, with IC ≮ ₀ value of 12.5 μ M.
2. Energy technology
Organic solar cells: As a donor material, after blending with fullerene derivatives, the photoelectric conversion efficiency is increased to 8.2%.
Lithium ion battery: 3,4,5-trimethoxybenzaldehyde polymer derivatives serve as solid electrolytes, with an ion conductivity of 10 ⁻ S/cm and excellent cycling stability at room temperature.
With its unique molecular structure and multifunctional reactivity, it has become an indispensable key intermediate in the fields of medicine, chemical engineering, materials science, and emerging industries.
Playing a pivotal role as an intermediate in the synthesis of sulfonamide drugs, a category renowned for its broad-spectrum antibacterial propertes. These drugs are extensively utilized in the medical field to combat a multitude of infections, including those affecting the urinary tract, respiratory system, and intestines, caused by susceptible bacterial strains.
The incorporation as a key intermediate facilitates the creation of sulfonamide derivatives that exhibit enhanced antibacterial activity and an expanded antibacterial spectrum. The methoxy groups attached to the benzaldehyde moiety modify the compound's electronic and physicochemical propertes, which in turn influence its binding affinity and interaction with bacterial targets. This leads to the development of more potent and effective antibiotics that can address a wider range of bacterial infections.
The synthesis process often involves the condensation with sulfonamide precursors, followed by additional chemical transformations to yield the desired sulfonamide drug. This intermediate's unique structure and reactivity make it an indispensable building block in the preparation of advanced therapeutic agents with superior antibacterial profiles.
In summary, the significance as an intermediate in sulfonamide drug synthesis cannot be overstated. Its contribution to the development of more effective antibiotics with broader antibacterial activity underscores its importance in the ongoing fight against bacterial infections.
In the pharmaceutical industry, it stands out as a crucial intermediate in the synthesis of Trimethoprim (TMP), an antibacterial enhancer that plays a significant role in enhancing the efficacy of sulfonamide drugs. TMP, when used in conjunction with sulfonamide antibiotics, exhibits a synergistic effect that not only amplifies the antibacterial activity of these drugs but also broadens their antibacterial spectrum and mitigates the risk of bacterial resistance development.
The incorporation into the TMP synthesis pathway is vital, as it contributes to the formation of a chemical structure that is essential for TMP's antibacterial enhancing propertes. This intermediate's specific reactivity and chemical propertes allow for the creation of TMP molecules that can effectively inhibit bacterial dihydrofolate reductase, an enzyme crucial for bacterial growth and replication. By blocking this enzyme, TMP disrupts bacterial folate metabolism, leading to bacterial cell death and, consequently, enhanced antibacterial activity.
The combination of TMP with sulfonamide drugs is particularly advantageous, as sulfonamides inhibit the synthesis of bacterial dihydropteroate, another essential component in folate metabolism. Together, these drugs create a double block in the folate synthesis pathway, making it more difficult for bacteria to develop resistance. This synergistic effect not only improves patient outcomes but also prolongs the usefulness of sulfonamide-based therapies by reducing the likelihood of bacterial resistance emergence.
In conclusion, its role as an intermediate in TMP synthesis underscores its importance in the pharmaceutical industry. Its contribution to the development of potent antibacterial combinations that enhance sulfonamide drug efficacy, broaden their antibacterial spectrum, and reduce drug resistance represents a significant advancement in antibacterial therapy.
It continues to demonstrate its versatility as an intermediate in the synthesis of various pharmaceutical compounds, including Tretoquinol, a drug used in the treatment of bronchial asthma and asthmatic bronchitis. Tretoquinol, also known as Tretoquinolum or its brand name Chuansu Ning, exhibits its anti-asthma effects through multiple mechanisms.
One of the primary mechanisms by which Tretoquinol alleviates asthma symptoms is by relaxing the bronchial smooth muscle. This action helps to widen the airways, making it easier for air to flow in and out of the lungs, thereby reducing the frequency and severity of asthma attacks. Additionally, Tretoquinol inhibits the release of inflammatory mediators, such as histamine and leukotrienes, which are known to contribute to airway inflammation and narrowing. By blocking the release of these mediators, Tretoquinol further reduces airway inflammation and improves breathing.
The synthesis of Tretoquinol often involves the use as a key intermediate. This compound's specific chemical propertes and reactivity make it an ideal building block for the creation of Tretoquinol's therapeutic structure. The incorporation into the synthesis pathway ensures that the final drug product possesses the necessary pharmacological propertes to effectively treat bronchial asthma and asthmatic bronchitis.
In summary, its role as an intermediate in the synthesis of Tretoquinol underscores its importance in the development of asthma treatment options. Its contribution to the creation of a drug that relaxes bronchial smooth muscle and inhibits inflammatory mediator release represents a significant advancement in the management of bronchial asthma and asthmatic bronchitis.
3,4,5-Trimethoxybenzaldehyde is an organic compound with a distinct chemical structure and propertes. This aromatic aldehyde features a benzaldehyde backbone where three methoxy (-OCH₃) groups are attached to the carbon atoms at positions 3, 4, and 5 of the benzene ring. The aldehyde functional group (-CHO) is located at the para position relative to these methoxy substituents, contributing to its unique reactivity and physical characteristics.
Due to the presence of three methoxy groups, it exhibits enhanced solubility in polar organic solvents such as ethanol and acetone compared to unsubstituted benzaldehyde. These methoxy groups also influence its electronic propertes, making it a valuable intermediate in the synthesis of various organic compounds, particularly those requiring specific substitution patterns and aldehyde functionality.
In the field of organic synthesis, it serves as a precursor for the preparation of dyes, pharmaceuticals, and agrochemicals. Its aldehyde group can undergo a wide range of reactions, including condensation, reduction, and oxidation, enabling the synthesis of complex molecules with diverse applications.
Moreover, the compound's UV-absorbing propertes and fluorescence make it useful in the development of optical materials and sensors. Researchers have also explored its potential in biological studies, particularly in understanding the interactions between small molecules and biological macromolecules.
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