Product Details
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73-31-4 Name |
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Name |
Melatonine |
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Synonym |
Melatonin (AS);Melatonine,N-(2-(5-Methoxyindol-3-yl)ethyl)acetaMide;MELATONINE FOR SYNTHESIS 1 G;MELATONINE FOR SYNTHESIS 5 G;Melatonin solution ;N-[2-(5-METHOXY-1H-INDOL-3-YL)ETHYL]ACETAMIDE;N-(2-(5-methoxyindol-3-yl)ethyl)acetamide;MLT |
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73-31-4 Biological Activity |
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Related Catalog |
Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> GPCR/G Protein >> Melatonin Receptor Signaling Pathways >> Neuronal Signaling >> Melatonin Receptor Signaling Pathways >> Autophagy >> Mitophagy Research Areas >> Neurological Disease Natural Products >> Others |
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Target |
Human Endogenous Metabolite |
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73-31-4 Chemical & Physical Properties |
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Melting point |
116.5-118 °C(lit.) |
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Boiling point |
459.8±55.0 °C at 760 mmHg |
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Density |
1.2±0.1 g/cm3 |
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Molecular Formula |
C13H16N2O2 |
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Molecular Weight |
232.278 |
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Flash Point |
231.9±31.5 °C |
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PSA |
54.12000 |
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LogP |
1.94 |
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Exact Mass |
232.121185 |
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Vapour Pressure |
0.0±1.2 mmHg at 25°C |
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Index of Refraction |
1.580 |
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Storage condition |
15°C |
Melatonin is a hormone that has been studied in various scholarly articles for its potential applications. One of its primary uses is as a sleep aid, as it is involved in the regulation of the sleep-wake cycle. It has been found to be effective in improving sleep quality and reducing the time it takes to fall asleep, particularly in individuals with sleep disorders such as insomnia. Additionally, Melatonin has been investigated for its potential applications in the treatment of various conditions, such as migraine, depression, and anxiety. It has also been studied for its potential antioxidant and anti-inflammatory properties, which may have applications in the prevention and treatment of certain diseases, such as cardiovascular disease and cancer. However, further research is needed to fully explore and understand the extent of its applications and potential benefits in these areas.
InChI:InChI=1/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
Water increases the selectivity in the Rh-phosphine catalysed hydroformylation of N-allylacetamide; an aqueous-organic biphasic system, containing a hydrophobic Rh-catalyst, provided facile catalyst/product separation, after which the aqueous product phase could be used in a one-pot synthesis of N-acetyl-5-methoxytryptamine (melatonin).
O-Methylation of N-acetylserotonin (NAS) has been identified as the bottleneck in melatonin biosynthesis pathway. In the present paper, caffeic acid O-methyltransferase from Arabidopsis thaliana (AtCOMT) was engineered by rational design to improve its catalytic efficiency in conversion of NAS to melatonin. Based on the notable difference in the terminal structure of caffeic acid and NAS, mutants were designed to strengthen the interactions between the substrate binding pocket of the enzyme and the terminal structure of the unnatural substrate NAS. The final triple mutant (C296F-Q310L-V314T) showed 9.5-fold activity improvement in O-methylation of NAS. Molecular dynamics simulations and binding free energy analysis attributed the increased activity to the higher affinity between the substrate terminal structure and AtCOMT, resulting from the introduction of N–H?π interaction by Phe296 substitution, hydrophobic interaction by Thr314 substitution and elimination of electrostatic repulsion by substitution of Gln310 with Leu310. This work provides hints for O-methyltransferase engineering and meanwhile lays foundation for biotechnological production of melatonin.
A new type of physiologically relevant nitrosamines have been recently recognized, the N1-nitrosoindoles. The possible pathways by which N1-nitrosomelatonin (NOMel) can react in physiological environments have been studied. Our results show that NOMel slowly decomposes spontaneously in aqueous solution, generating melatonin as the main organic product (k = (3.7 ± 1.1) × 10-5 s-1, Tris-HCl (0.2 M) buffer, pH 7.4 at 37°C, anaerobic). This rate is accelerated by acidification (kpH 5.8 = (4.5 ± 0.7) × 10-4 s-1, kpH 8.8 = (3.9 ± 0.6) × 10-6 s-1 Tris-HCl (0.2 M) buffer at 37°C), by the presence of O2 (k o = (9.8 ± 0.1) × 10-5 s-1 pH 7.4, 37°C, [NOMel] = 0.1 mM, P(O2) = 1 atm), and by the presence of the spin trap TEMPO (2,2,6,6-tetramethylpiperidine 1-oxyl; ko = (2.0 ± 0.1) × 10-4 s-1, pH 7.4, 37°C, [NOMel] = 0.1 mM, [TEMPO] = 9 mM). We also found that NOMel can transnitrosate to L-cysteinate, producing S-nitrosocysteine and melatonin (k = 0.127 ± 0.002 M-1 s-1, Tris-HCl (0.2 M) buffer, pH 7.4 at 37°C). The reaction of NOMel with ascorbic acid as a reducing agent has also been studied. This rapid reaction produces nitric oxide and melatonin. The saturation of the observed rate constant (k = (1.08 ± 0.04) × 10-3 s-1, Tris-HCl (0.2 M) buffer, pH 7.4 at 37°C) at high ascorbic acid concentration (100-fold with respect to NOMel) and the pH independence of this reaction in the pH range 7-9 indicate that the reactive species are ascorbate and melatonyl radical originated from the reversible homolysis of NOMel. Taking into account kinetic and DFT calculation data, a comprehensive mechanism for the denitrosation of NOMel is proposed. On the basis of our kinetics results, we conclude that under physiological conditions NOMel mainly reacts with endogenous reducing agents (such as ascorbic acid), producing nitric oxide and melatonin.
1-Hydroxymelatonin, 5-bromo- and 5,7-dibromo-1-hydroxytryptamine derivatives, 1,4-dihydroxy-5-nitroindole, 1-hydroxy-3-methylsulfinylmethylindole, and 5-acetyl-1,3,4,5-tetrahydro-1-hydroxypyrrolo[4,3,2-de]quinoline were synthesized for the first time. 1-Hydroxyindoles revealed potent inhibitory activities on platelet aggregation.
The pineal hormone melatonin is conveniently prepared in simple one pot operation by treating 4-methoxyphenylhydrazine hydrochloride(6) with acetic anhydride and 4-aminobutyraldehyde dimethylacetal(4) in a mixed solvent system of acetic acid/ethanol/water.
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The structures of melatonin and ferulic acid were merged into tertiary amide-based histone deacetylase 6 (HDAC6) inhibitors to develop multi-target-directed inhibitors for neurodegenerative diseases to incorporate antioxidant effects without losing affinity and selectivity at HDAC6. Structure-activity relationships led to compound 10b as a hybrid molecule showing pronounced and selective inhibition of HDAC6 (IC50 = 30.7 nM, > 25-fold selectivity over other subtypes). This compound shows comparable DPPH radical scavenging ability to ferulic acid, comparable ORAC value to melatonin and comparable Cu2+ chelating ability to EDTA. It also lacks neurotoxicity on HT-22 cells, exhibits a pronounced immunomodulatory effect, and is active in vivo showing significantly higher efficacy in an AD mouse model to prevent both Aβ25-35-induced spatial working and long-term memory dysfunction at lower dose (0.3 mg/kg) compared to positive control HDAC6 inhibitor ACY1215 and an equimolar mixture of the three entities ACY1215, melatonin and ferulic acid, suggesting potentially disease-modifying properties.
The invention discloses a synthesis method of melatonin, and belongs to the technical field of pharmaceutical chemistry synthesis. According to the method, 5-hydroxytryptamine hydrochloride is used as a raw material, 5-methoxytryptamine is obtained through a methylation reaction of hydroxyl through a one-pot feeding method, a crude melatonin product is prepared through an acetylation reaction of amino, and finally, the finished melatonin is obtained through one-step refining and purification. The melatonin synthesis method provided by the invention avoids waste caused by step-by-step purification of the product, and has the characteristics of short synthesis route, short synthesis period, few raw material types and the like, the obtained product is high in yield, and the purity can meet the market demand. The synthesis method of the melatonin provided by the invention saves the cost and is easy for industrial production.
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.
2-(5-methoxyindol-3-yl)ethylamine
acetyl chloride
5-methoxy-N-acetyl-tryptamine
| Conditions | Yield |
|---|---|
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In dichloromethane; at 25 - 30 ℃; Temperature;
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98.3% |
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With triethylamine; In toluene; at 8 - 20 ℃; for 7.5h; Inert atmosphere;
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92.6% |
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With triethylamine; In dichloromethane; at 20 ℃;
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|
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With triethylamine; In dichloromethane; at 0 - 20 ℃; for 5h;
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5-methoxytryptamine hydrochloride
acetic anhydride
5-methoxy-N-acetyl-tryptamine
| Conditions | Yield |
|---|---|
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With triethylamine; In dichloromethane; at 0 - 25 ℃; for 3h;
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90% |
5-methoxyindole-3-acetonitrile
Nb,Nb-diacetyl-5-methoxytryptamine
4-methoxyphenylhydrazine hydrochloride
N-acetyl-2-methoxypyrrolidine
2-(2,4-dinitrophenylsulfenyl)melatonin
2',3'-O-isopropylideneuridine
5-<3-<2-(acetylamino)ethyl>-5-methoxy-1H-indol-2-yl>-2',3'-O-(1-methylethylidene)uridine
2-iodomelatonin
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