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5-Hydroxyindole, is an organic compound that is a white to pale yellow needle shaped or sheet-like crystal with a light special odor. It can be soluble in organic solvents such as water, alcohol, ether, and chloroform, and its solubility is influenced by factors such as temperature, pH value, solvent type, and concentration. It is relatively stable at room temperature and pressure, but oxidation reactions may occur in the presence of light, oxygen, and certain metal ions. The molecule contains an indole ring and a hydroxyl group, with a specific spatial configuration and electron distribution. It has a certain acidity and can be used as an acid to neutralize a base. Its hydroxyl group can undergo proton transfer reaction, causing a change in the pH value of the solution. It exhibits specific kinetic behaviors in some chemical reactions, such as the rate constant and activation energy of oxidation reactions. In the study of neurotransmitters, they play an important role in the research and design of potential drug targets or lead compounds in some drug development processes. By studying the structure and properties of 5 Hydroxyindole, potential therapeutic molecules can be discovered and developed. It also has certain application value in the development of biological analysis methods. For example, analytical methods such as high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS) can be used to detect changes in the content of 5 hydroxyindole, in order to evaluate its metabolism and function in living organisms.
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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 |
5-hydroxyindoleacetic acid (5-HIAA), also known as 5-hydroxyindole, is an important neurotransmitter compound with significant impact on neurological diseases.
1. In neurotransmitter research, the application of 5 Hydroxyindole is mainly reflected in the following aspects:
(1) Research on neurotransmitter synthesis: 5 Hydroxyindole is one of the metabolites of serotonin (5-HT) and plays an important role in the synthesis, metabolism, and function of 5-HT. Studying the synthesis and metabolic pathways of 5 Hydroxyindole helps to gain a deeper understanding of the synthesis and metabolic mechanisms of neurotransmitters, providing a theoretical basis for the treatment of neurological diseases.
(2) Research on the mechanism of action of neurotransmitters: 5 Hydroxyindole, as an important neurotransmitter compound, participates in signal transmission in the central nervous system. Studying the mechanism of action of neurotransmitters helps to gain a deeper understanding of the working principles of the nervous system and the mechanisms of disease occurrence.
(3) Neurotransmitter function research: 5 Hydroxyindole, as a metabolite of serotonin, is involved in regulating emotional, behavioral, and cognitive functions. Studying the role of 5 Hydroxyindole in neurotransmitter function can help discover new drug targets and treatment strategies.
(4) Research on neurotransmitter related diseases: 5 hydroxyindole is closely related to various neurological diseases such as depression, anxiety, schizophrenia, etc. Studying the metabolic and functional changes of 5 hydroxyindole in these diseases can help to gain a deeper understanding of the pathogenesis and treatment strategies of the disease.
2. The application in the development of biological analysis methods is mainly reflected in their detection and analysis as biomarkers and metabolites. Due to its stability and specificity in living organisms, 5 Hydroxyindole can serve as a reliable biomarker for monitoring and diagnosing certain neurological diseases and mental disorders.
(1) Urine and blood detection: By using techniques such as high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS), the content of 5 hydroxyindole in urine and blood can be detected, which is used to evaluate the metabolic status of neurotransmitters and the condition of related diseases. This detection method has the advantages of non-invasive, simple, and reliable, and is suitable for clinical diagnosis and drug development.
(2) Fluorescence detection method: By labeling 5 Hydroxyindole with fluorescent substances and using fluorescence spectroscopy analysis technology, the content of 5 Hydroxyindole in biological samples can be sensitively detected. This method has high sensitivity and selectivity, which helps to further study the metabolism and function of 5 Hydroxyindole in organisms.
(3) Enzyme linked immunosorbent assay (ELISA): By preparing specific antibodies and using enzyme labeling technology, an enzyme-linked immunosorbent assay method for 5 hydroxyindole is established. This method can be used for rapid detection of a large number of samples, with the advantages of simple operation, high sensitivity, and good specificity, and is suitable for clinical and scientific research fields.
(4) Microdialysis sampling technology: Combined with microdialysis sampling technology and liquid chromatography-mass spectrometry analysis, real-time and online monitoring of 5 hydroxyindole in living organisms can be achieved. This method helps to understand the dynamic changes of 5 hydroxyindole in organisms, providing new research tools for drug development and neuroscience.
Detailed steps for laboratory synthesis of 5-Hydroxyindole:
C8H7N + H2O → C8H9NO
Synthesis steps:
a. Dissolve Indole: Add an appropriate amount of indole to the flask, then add an appropriate amount of water and stir with a magnetic stirrer until the indole is completely dissolved. Indole is solid at room temperature and easily soluble in hot water.
b. Add sodium chloride and activated carbon: After the indole is completely dissolved, add an appropriate amount of sodium chloride and activated carbon, and continue stirring evenly. The function of sodium chloride is to increase the ion strength of the solution and promote the reaction; Activated carbon is used to adsorb impurities and colors from the solution.
c. Acidification: Slowly add concentrated hydrochloric acid to the solution while keeping the solution in a boiling state. Hydrochloric acid is added to provide hydrogen ions and form more stable intermediates with the reactants.
d. Nitrification reaction: Continue to slowly add concentrated nitric acid to the boiling solution, paying attention to controlling the addition rate to avoid accidents caused by excessive reaction. In nitration reactions, nitrate ions act as electrophilic reagents and undergo electrophilic substitution reactions with intermediates to generate 5-nitroindole.
e. Reduction reaction: After the nitrification reaction is completed, slowly add an appropriate amount of concentrated sulfuric acid to the solution while keeping the solution in a boiling state. The function of concentrated sulfuric acid is to provide hydrogen ions and sulfate ions, which undergo a reduction reaction with nitro groups to produce 5-aminoindole.
f. Hydrolysis and diazotization reaction: Cool the reduced 5-aminoindole solution to room temperature, then add an appropriate amount of water and adjust the pH to acidic conditions with concentrated hydrochloric acid. Under acidic conditions, 5-aminoindole undergoes hydrolysis and diazotization reactions, producing diazonium salts.
g. Coupling reaction: Mix diazonium salt solution with an appropriate amount of sodium hydroxide solution, adjust the pH value to alkaline conditions. Under alkaline conditions, diazonium salts undergo coupling reactions to form the substance.
h. Post treatment: Filter the reaction solution with filter paper to remove insoluble substances, and then pour the filtrate into an evaporating dish. Heat and evaporate excess water until a dark solid is obtained. At this point, the solid is the crude product.
i. Recrystallization: High purity crystals can be obtained by recrystallizing and purifying crude 5-Hydroxyindole. Recrystallization is a method of removing impurities and improving the purity of compounds through a dissolution crystallization process. The specific operation is as follows: add the crude product to the beaker, add an appropriate amount of hot solvent to completely dissolve it. Then slowly cool the solution to room temperature to allow the crystals to precipitate. Filter and collect crystals, wash with a small amount of solvent. Dry the crystals in a vacuum drying oven to obtain pure 5-Hydroxylindole.
Safety: Systematic assessment from toxicity to protective measures
Melting point and boiling point: The melting point is 106-108°C, and the boiling point is approximately 343°C (760 mmHg), indicating that it is in a solid state at room temperature and has high thermal stability.
Solubility: It is soluble in organic solvents such as ethanol and DMSO, but has a low solubility in water (about 38 g/L), and the choice of solvent should be noted for its impact on reaction efficiency.
Phototoxicity: This substance is sensitive to light, and long-term exposure to light may lead to degradation, requiring protection from light (using brown reagent bottles);
Air sensitivity: It may absorb moisture and form lumps in humid air, and should be stored sealed and dry; it is recommended to be filled with inert gases (such as nitrogen) for protection.
Heat decomposition risk: It may decompose and produce toxic gases (such as carbon monoxide, nitrogen oxides) at high temperatures, and should be kept away from heat sources and high-temperature environments.
Temperature control: Short-term storage can be placed in a refrigerator at 0-6°C, and long-term storage requires freezing at -20°C or below to delay degradation.
Packaging requirements: Use sealed glass or polyethylene containers to avoid contact with metal ions (such as iron, copper), and prevent catalytic degradation.
Stability period: Under recommended storage conditions, the validity period is usually over 2 years, but regular purity and impurity content testing is required.
Oxidation reaction: It may be oxidized to quinone compounds in the presence of strong oxidants (such as potassium permanganate), and should be avoided mixed storage.
Acid-base stability: It may undergo ring-opening or hydrolysis reactions in acidic or alkaline conditions, and the pH value of the reaction should be controlled.
Metal catalysis: Contact with certain metals (such as palladium, nickel) may cause catalytic degradation, and an inert catalyst should be selected.
Stability: Comprehensive consideration from storage conditions to reaction activity
Physical stability
Melting point and boiling point: The melting point is 106-108°C, and the boiling point is approximately 343°C (760 mmHg), indicating that it is in a solid state at room temperature and has high thermal stability.
Solubility: It is soluble in organic solvents such as ethanol and DMSO, but has a low solubility in water (about 38 g/L), and the choice of solvent should be noted for its impact on reaction efficiency.
Chemical stability
Phototoxicity: This substance is sensitive to light, and long-term exposure to light may lead to degradation, requiring protection from light (using brown reagent bottles);
Air sensitivity: It may absorb moisture and form lumps in humid air, and should be stored sealed and dry; it is recommended to be filled with inert gases (such as nitrogen) for protection.
Heat decomposition risk: It may decompose and produce toxic gases (such as carbon monoxide, nitrogen oxides) at high temperatures, and should be kept away from heat sources and high-temperature environments.
Optimized storage conditions
Temperature control: Short-term storage can be placed in a refrigerator at 0-6°C, and long-term storage requires freezing at -20°C or below to delay degradation.
Packaging requirements: Use sealed glass or polyethylene containers to avoid contact with metal ions (such as iron, copper), and prevent catalytic degradation.
Stability period: Under recommended storage conditions, the validity period is usually over 2 years, but regular purity and impurity content testing is required.
Reaction activity and compatibility
Oxidation reaction: It may be oxidized to quinone compounds in the presence of strong oxidants (such as potassium permanganate), and should be avoided mixed storage.
Acid-base stability: It may undergo ring-opening or hydrolysis reactions in acidic or alkaline conditions, and the pH value of the reaction should be controlled.
Metal catalysis: Contact with certain metals (such as palladium, nickel) may cause catalytic degradation, and an inert catalyst should be selected.
Safety and stability practices in industry applications
As precursors to serotonin and melatonin, their stability directly impacts drug purity. Production requires strict monitoring of temperature, light exposure, and humidity to prevent side reactions.
Case Study: A pharmaceutical company resolved product degradation caused by storage temperature fluctuations by optimizing cryogenic storage conditions.
When studying 5-HT3 receptor function, reagent purity (≥98%) must be ensured to prevent impurities from interfering with experimental results.
Protection Recommendations: Laboratories should be equipped with biosafety cabinets, and operators must receive specialized training to reduce long-term exposure risks.
Inert gas protection and automated control systems can significantly reduce human operational risks while enhancing product stability.
Trend: The adoption of green chemistry processes (e.g., solvent-free synthesis) holds promise for further alleviating safety and environmental pressures.
Frequently Asked Questions
Why is it rarely used as a supplement as a direct precursor of serotonin?
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Because it is difficult to effectively cross the blood-brain barrier and enter the central nervous system, and peripheral administration (such as oral administration) is preferentially metabolized into inactive products such as 5-hydroxyindoleacetic acid by monoamine oxidase (MAO) and aldehyde dehydrogenase in the liver, lungs, etc., it cannot effectively increase the level of serotonin in the brain.
Why is it a key biomarker for the diagnosis of "carcinoid syndrome" in oncology?
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Cancer like tumor cells convert large amounts of tryptophan into serotonin and its metabolites. The abnormal elevation of 5-hydroxyindole and its main metabolite 5-hydroxyindoleacetic acid in blood or urine is direct and specific laboratory evidence for the diagnosis of this syndrome.
It exists in a "free" form in plants (such as bananas and tomatoes), which is fundamentally different from its role in animals?
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In plants, it does not directly act as a neurotransmitter precursor. Its function may be related to growth and development regulation, antioxidant stress, or it may be a defensive alkaloid intermediate against herbivorous animals, with functions completely different from those in animal bodies.
Why is it a unique tool for studying the gut brain axis and the gut 5-hydroxytryptamine system?
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About 90% of serotonin in the human body is produced by chromaffin cells in the intestine. 5-hydroxyindole can be locally absorbed in the intestine and directly converted into serotonin, affecting intestinal peristalsis, secretion, etc., without affecting the brain. This makes it an ideal molecular tool for precise research on the separation function of peripheral and central serotonin systems.
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