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4-Hydroxyindole is an organic compound with the molecular formula C8H7NO. A solid powder with a grayish white to light yellow color, insoluble in water but soluble in organic solvents such as ether, chloroform, and methanol. In the molecular structure, a phenolic hydroxyl group replaces the hydrogen atom on the indole ring, giving the molecule some special properties. It has a low solubility in water and is almost insoluble in water, but it has a high solubility in organic solvents. It is easy to oxidize in the air, especially under alkaline conditions, and is more prone to oxidation reactions, generating dark substances. Therefore, it is necessary to avoid contact with air as much as possible during storage and use. There are two configurations, trans and cis, with the trans configuration being more stable. Under certain conditions, the cis configuration can be transformed into a trans configuration. Under ultraviolet light, it can emit strong fluorescence due to its conjugated double bonds and hydroxyl groups. In addition, structural identification and quantitative analysis can be carried out through methods such as infrared spectroscopy and nuclear magnetic resonance spectroscopy.
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Chemical Formula |
C8H7NO |
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Exact Mass |
133 |
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Molecular Weight |
133 |
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m/z |
133 (100.0%), 134 (8.7%) |
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Elemental Analysis |
C, 72.17; H, 5.30; N, 10.52; O, 12.02 |
4-Hydroxyindole (CAS number 2380-94-1) is an organic compound containing an indole ring structure, with the molecular formula C ₈ H ₇ NO and a molecular weight of 133.15. Its solid state is white to light brown crystals, with a melting point of 97-99 ℃. It is slightly soluble in water and easily soluble in organic solvents such as acetone. Due to the high reactivity of the indole ring and the polarity of the hydroxyl group, it has shown extensive application potential in fields such as medicine, materials science, and biochemistry.
1. Synthesis of β - adrenergic receptor antagonists
It is a key intermediate in the synthesis of beta blockers. For example, research in the German Journal of Medicinal Chemistry has confirmed that it can be converted into classic drugs such as propranolol by condensing with isopropylamine to form an indole ring side chain. This type of medication is widely used to treat hypertension, angina, and arrhythmia by blocking beta adrenergic receptors, reducing heart rate and blood pressure.
2. Development of substances related to the treatment of mental illnesses
As an intermediate of serotonin substances such as Psilocybin and Psilocin, it is the core skeleton for synthesizing hallucinogens. Although its direct application is strictly regulated, its derivatives have important value in exploring the mechanisms of mental illnesses such as depression and anxiety in neuroscience research. For example, the latest research in 2025 shows that it has been used for the development of a platform for microbial synthesis of fipronil, providing a new path for the study of psychotropic drugs.
3. Research and development of antioxidant and anti-inflammatory drugs
Its hydroxyl group can participate in hydrogen atom transfer reactions, endowing it with antioxidant activity. Research has shown that it can clear free radicals, inhibit lipid peroxidation, and block the release of inflammatory factors such as TNF - α and IL-6. Based on this, researchers are exploring its potential as an anti-inflammatory drug or adjuvant therapy, especially in neurodegenerative diseases such as Alzheimer's disease, where it can inhibit amyloid fibrosis and protect neurons from toxic damage.
4. Potential for the treatment of metabolic diseases
Animal experiments have shown that it can cause thyroid dysfunction and blood glucose changes in mice, suggesting that it may affect metabolic balance by regulating hormone secretion. Although its toxicity (LD ₅₀=620 mg/kg, intracranial injection) needs to be carefully evaluated, this characteristic provides new ideas for the development of metabolic regulatory drugs.
1. Organic light-emitting diode (OLED) materials
Its conjugated system can enhance the material's light absorption and emission capabilities. Indole based polyether sulfone (PESI) can be prepared by condensation reaction using 4-Hydroxxyindole and 4,4 '- difluorodiphenyl sulfone as raw materials. The PESI ultra-thin film prepared by spin coating method has high transparency and thermal stability, and is suitable as a substrate material for flexible OLED displays. Further introduction of Mg ² ⁺ to construct PESI-Mg ² ⁺ composite films through cation - π interactions resulted in a 45.9% increase in tensile strength and a 27.9% increase in elongation at break, providing an example for the development of high-performance optical materials.
2. Materials for photoelectric sensors
The π - electron system of indole ring is sensitive to light and electrical signals, and 4-hydroxyindole derivatives can be used to construct photoelectric sensors. For example, the conjugated system formed by its combination with porphyrin compounds can efficiently detect heavy metal ions (such as Pb ² ⁺, Cd ² ⁺) with detection limits as low as ppb, making it suitable for environmental monitoring and biological imaging.
3. High performance polymer additives
Adding polyimide, epoxy resin and other engineering plastics can improve the heat resistance and mechanical properties of the materials. Its hydroxyl groups form hydrogen bonds with polymer chains, enhancing intermolecular forces and maintaining a stable structure at high temperatures. It is widely used in the fields of aerospace and electronic packaging.
1. Enzyme activity inhibitors
Can specifically inhibit the activity of certain oxidoreductases. For example, it competitively binds to the active site of monoamine oxidase (MAO), blocking the degradation of neurotransmitters such as serotonin and dopamine, thereby regulating neural signal transmission. This characteristic makes it an important tool for studying enzyme function and drug targets.
2. Metabolic pathway research model
In drug metabolism research, as a metabolic intermediate of cannabinoid JWH-018, it helps to reveal its in vivo transformation mechanism.
Research in the Journal of Pharmaceutical and Biomedical Analysis shows that JWH-018 is catalyzed by cytochrome P450 enzymes in liver microsomes to produce 4-Hydroxxyindole derivatives, which are then excreted. This discovery provides a key basis for evaluating the toxicological effects of cannabinoids.
3. Development of cell protectants
In neural cell models, dose-dependent inhibition of amyloid (A β 1-42) - induced toxicity can protect PC12 cells from apoptosis. Its mechanism may be related to clearing reactive oxygen species (ROS) and stabilizing mitochondrial membrane potential, providing candidate molecules for the development of neuroprotective drugs.
1. Innovation in the dye industry
4-Hydroxxyindole and its derivatives can be used to develop novel cationic dyes by introducing quaternized aliphatic chains. This type of dye has a high affinity for keratin fibers (such as wool and hair), with long-lasting dyeing effects and bright colors. For example, oxidative dyes containing their structure can achieve precise regulation from light brown to black in hair dyeing, and have low irritation to the scalp.
2. Laboratory safety and protection
Although 4-hydroxxyindole is widely used in scientific research, its danger cannot be ignored. According to the GHS classification criteria, it poses risks of skin irritation (H315), eye injury (H319), and respiratory irritation (H335). The experimental operation should be carried out in a fume hood, wearing protective gloves and goggles, and stored away from sources of fire and oxidants. It is recommended to use anti-static containers for storage.
The resorcinol method is a commonly used method for synthesizing 4-hydroxxyindole. The following are the detailed steps and chemical equations of this method:
Heat resorcinol to a molten state, then slowly add concentrated hydrochloric acid while stirring and heating. React at a temperature of approximately 70 ℃ for a period of time until resorcinol is completely dissolved. Then, pour the reaction mixture into ice water, adjust it to slightly acidic with a small amount of concentrated hydrochloric acid, and then extract with ether. Dry the extraction solution with anhydrous sodium sulfate, filter and recover ether to obtain 4-hydroxybenzoic acid.
Chemical equation:
C6H4(OH)2 → HOOC-C6H4-COOH
Dissolve 4-hydroxybenzoic acid in ethanol, add a certain amount of catalyst (such as palladium carbon), and carry out hydrogenation reaction at a certain temperature and pressure. After a period of reaction, filter the mixture, extract the filtrate with ether, dry the extract with anhydrous sodium sulfate, filter and recover ether to obtain 4-aminobenzoic acid.
Chemical equation:
HOOC-C6H4-COOH + 2H2 → HOOC-C6H4-CH2NH2
Mix 4-aminobenzoic acid with ethyl bromopyruvate and undergo cyclization reaction at a certain temperature. After a period of reaction, filter the mixture, extract the filtrate with ether, dry the extract with anhydrous sodium sulfate, filter and recover ether to obtain product.
Chemical equation:
HOOC-C6H4-CH2NH2 + BrCH2COOEt → H2N-C6H4-CHBrCOOEt → C8H7NO+C4H8O2 + HBr
The above are the detailed steps and chemical equations for the synthesis of 4-Hydroxyindole using resorcinol method. It should be noted that toxic or harmful raw materials and solvents should be avoided as much as possible during the synthesis process to reduce negative impacts on the environment and human health. Meanwhile, different synthesis methods and conditions can be selected and optimized according to actual needs to obtain high-quality products.
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