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2,5-Dihydroxybenzaldehyde is an organic compound with the molecular formula C7H6O3 and CAS 1194-98-5. It is a light yellow crystalline form, usually present in powder or crystal form, with a special aldehyde taste, similar to the odor of bitter almonds. During the melting process, it will gradually turn yellow and sublimate at high temperatures. It can be soluble in water, but its solubility is not high. It is also slightly soluble in organic solvents such as alcohols and ethers. This compound consists of a benzene ring, an aldehyde group, and a hydroxyl group. Among them, the aldehyde group is located at the adjacent position of the benzene ring, and both hydroxyl groups are located at the intermediate position of the benzene ring. It is a reducing compound that can react with alkali to generate corresponding phenolic salts. It can undergo benzoin condensation reaction with acetaldehyde under acidic conditions, producing benzoic acid. In addition, it can also undergo nucleophilic addition reactions with ammonia or amine compounds. There are various uses in the preparation of benzoin, including as an aldehyde source, protectant, condensation agent, impurity removal, catalyst, solvent, pre-treatment raw material, modification of structure, and synthesis of analogues. These uses make the product an indispensable and important compound in the process of preparing benzoin.
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Chemical Formula |
C7H6O3 |
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Exact Mass |
138 |
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Molecular Weight |
138 |
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m/z |
138 (100.0%), 139 (7.6%) |
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Elemental Analysis |
C, 60.87; H, 4.38; O, 34.75 |
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Chemical Formula: C7H6O3, Exact Mass: 138.03, Molecular Weight: 138.12, m/z: 138.03 (100.0%), 139.04 (7.6%), Elemental Analysis: C, 60.87; H, 4.38; O, 34.75
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Additional information of chemical compound: Melting point 97-99 °C (lit.), Boiling point 213.5°C (rough estimate), Density 1.2667 (Rough estimate), Refractive index 1.4797 (Estimate), Storage Store below +30°C, Solubility 13.8g/L soluble
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2,5-Dihydroxybenzaldehyde can be synthesized in the laboratory through various methods. The following is one of the commonly used synthesis methods, along with detailed steps and corresponding chemical equations:
Synthesis method:
Raw materials and reagents: catechol, stannous chloride, concentrated hydrochloric acid, concentrated ammonia water, sodium carbonate, activated carbon.
Equipment: Round bottomed flask, condenser tube, and separating funnel.
Steps:
1. Add catechol to a round bottomed flask, then slowly add stannous chloride while stirring, and the temperature inside the flask will rise.
2. Continue to add an appropriate amount of concentrated hydrochloric acid, then heat and reflux the reaction for a period of time, allowing catechol to fully react with stannous chloride to produce dichlorophenoxyethanol.
3. Cool the reaction solution to room temperature, then add an appropriate amount of concentrated ammonia water to achieve a neutral pH value of the solution.
4. Wash the upper organic layer in a separating funnel with sodium carbonate solution to remove unreacted stannous chloride and hydrochloric acid, and then add an appropriate amount of activated carbon for decolorization.
5. Filter and remove the activated carbon, then perform column chromatography to separate and purify the product.
Chemical equation:
C6H4(OH)2 + SnCl2 + 2HCl → C6H4(OCH2Cl)2 + SnCl2 + 2H2O
C6H4(OCH2Cl)2 + 2NH3 → C6H4(OH)(OC2H5)2 + 2NH4Cl
C6H4(OH)(OC2H5)2 + H2O → C6H4(OH)CHO + 2C2H5OH
In the above synthesis method, the first step is to generate dichlorophenoxyethanol by reacting catechol and stannous chloride with hydrochloric acid; The second step is to adjust the pH of the neutral solution of dichlorophenoxy ethanol to neutral by adding ammonia water; The third step is to separate and purify the product through column chromatography.
2,5-Dihydroxybenzaldehyde has multiple uses in the preparation of benzoin.
1. The aldehyde source for synthesizing benzoin: can be used as the aldehyde source for synthesizing benzoin. Benzoin is a compound with a special aroma, widely used in fields such as spices, medicine, and cosmetics. By using 25 dihydroxybenzaldehyde as a raw material, various types of benzoin can be conveniently synthesized, such as type A benzoin, type B benzoin, etc.
2. Aldehyde protecting agent: In the process of synthesizing benzoin, it can also be used as a protective agent for aldehyde groups. Due to the fact that aldehyde groups are active functional groups that are easily oxidized or react with other compounds, the use of this substance can protect aldehyde groups, improve synthesis efficiency and yield.
3. Condensing agent: can be used as a condensing agent to synthesize benzoin. In a condensation reaction, it can react with another compound to generate a new compound, such as Knoevenagel condensation with benzaldehyde to produce benzoic acid.
4. Removing impurities: In the process of synthesizing benzoin, there are often some impurities, such as unreacted raw materials and by-products. The use of this product can easily remove these impurities, improve the purity and quality of the product.
5. Catalyst: It can be used as a catalyst in the process of synthesizing benzoin. By using catalysts, the reaction rate can be accelerated, and the yield and quality of products can be improved.
6. Solvent: In the process of synthesizing benzoin, it can be used as a solvent. It can dissolve some insoluble raw materials or products, improving the efficiency of the reaction.
7. Pre treated raw materials: Before synthesizing benzoin, this substance can be used to pre treat the raw materials. For example, it can react with raw materials to generate intermediates such as semi acetals or acetals, facilitating subsequent synthesis steps.
8. Structure modification: By using this substance as a modifier, specific modifications can be made to the structure of benzoin. For example, other functional groups can be introduced or the position of substituents can be changed.
9. Synthetic analogues: This product allows for the convenient synthesis of compounds similar to benzoin. These compounds have similar properties and uses to benzoin, but may have slightly different structures.
10. Research purpose: It is also an important experimental reagent for studying the synthesis and properties of benzoin. By using it and other experimental reagents, it is convenient to conduct synthesis experiments and mechanism studies.
2,5-Dihydroxybenzaldehyde (CAS No. 1194-98-5), also known as 2,5-dihydroxybenzaldehyde or gentian aldehyde, has a wide range of research value and application potential in the pharmaceutical field. The following is a detailed analysis of its research, application cases and development status in the pharmaceutical field:
1. Research value
2,5-Dihydroxybenzaldehyde acts as a natural anti-microbial agent with inhibitory effects on a wide range of microorganisms, which makes it potentially valuable for application in the pharmaceutical field. In addition, its unique chemical structure provides new ideas for new drug development.
2. Application Cases
Antimicrobial agent:
Studies have shown that 2,5-Dihydroxybenzaldehyde has significant antibacterial activity against bacteria such as Staphylococcus aureus, so it can be used as an antibacterial agent for the disinfection treatment of medical equipments and medicines.
Pharmaceutical intermediates:
In the process of pharmaceutical synthesis, 2,5-Dihydroxybenzaldehyde can be used as an important intermediate in the synthesis of compounds with specific pharmacological activities. For example, it can be used to synthesize drugs with anti-tumor activity.
New drug discovery:
Due to its ability to inhibit the growth and proliferation of microorganisms, 2,5-Dihydroxybenzaldehyde has also been widely recognized in new drug discovery. Researchers are exploring its potential as a new drug candidate with a view to developing new drugs with more efficient and safer antimicrobial effects.
3. Development status
Research progress:
At present, scholars at home and abroad have carried out in-depth research on the antibacterial mechanism, pharmacological effects and synthetic methods of 2,5-Dihydroxybenzaldehyde. By modifying and optimizing its chemical structure, its antibacterial activity and pharmacological effect can be further improved.
Application development:
With the deepening of the research on 2,5-Dihydroxybenzaldehyde, its application scope in the field of medicine is also expanding. In addition to being used as an antimicrobial agent and pharmaceutical intermediate, researchers are also exploring its application in new drug development, drug delivery systems and biomedical materials.
Market demand:
With the growing concern for health and quality of medical care, the demand for drugs and medical supplies with efficient and safe antimicrobial effects is increasing. Therefore, the application of 2,5-Dihydroxybenzaldehyde in the field of medicine is promising, and the market demand potential is huge.
In summary, 2,5-Dihydroxybenzaldehyde has extensive research value and application potential in the pharmaceutical field. With the deepening of research and the continuous progress of technology, it is believed that its application in the pharmaceutical field will be more extensive and in-depth.
adverse reaction
2,5-dihydroxybenzaldehyde is an important organic compound with a molecular formula of C ₇ H ₆ O ∝ and a yellow crystalline powder appearance. As an intermediate in the pharmaceutical and dye chemical industries, it is widely used in laboratory research and synthesis processes, such as playing a key role in antibacterial drug synthesis, natural product extraction, and organic synthesis reactions. However, its chemical properties determine that it may cause a series of adverse reactions during use.
Toxicity mechanism and classification of adverse reactions
Skin and mucosal irritation
Direct contact: Powder or solution can cause skin redness, itching, and even contact dermatitis. The mechanism involves cross-linking between aldehyde groups and skin proteins, disrupting the stratum corneum barrier.
Eye exposure: 0.1% solution can cause conjunctival congestion and tearing, and high concentrations (>5%) may cause corneal epithelial damage.
Respiratory irritation
Inhalation of dust or aerosols can irritate the upper respiratory mucosa, causing coughing and sore throat. Animal experiments showed that rats inhaled LC ₅₀ at a concentration of 4.2 mg/L (4-hour exposure).
Gastrointestinal reactions
In ingestion or oral experiments, a dose of 0.5 g/kg can cause reduced activity and rapid breathing in mice, with a mortality rate of 30% within 1 hour. The main mechanism is the direct corrosion of gastrointestinal mucosa by aldehyde groups.
Chronic exposure risk
Organ toxicity
Liver: Long term exposure (>90 days, 50 mg/kg/d) leads to edema and steatosis of rat liver cells, with a 2-3 fold increase in serum ALT/AST levels.
Kidney: vacuolization of proximal tubular epithelial cells and increased urinary NAG enzyme activity indicate tubular injury.
Neurological system: Exposure to high doses (200 mg/kg/d) resulted in decreased motor coordination in mice and a 15% decrease in dopamine levels in brain tissue.
Genotoxicity
Ames test: The TA98 strain showed weak positivity in the absence of S9 activation conditions (with a 1.8-fold increase in the number of revertant colonies).
Rodent micronucleus test: After intraperitoneal injection of 50 mg/kg in mice, the micronucleus rate of bone marrow cells increased from 0.2% to 0.8%.
Carcinogenicity controversy
Animal experiment: After oral administration to rats for 2 years, the incidence of hepatocellular carcinoma in the 50 mg/kg/d group increased from 8% to 15%, but did not reach statistical significance.
Human data: Currently, there is no epidemiological evidence to support its carcinogenicity, but IARC has not classified it.
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