6-Hydroxymelatonin

Base Information

• Chemical Name: 6-Hydroxymelatonin
• CAS No.: 2208-41-5
• Molecular Formula: C₁₃H₁₆N₂O₃
• Molecular Weight: 248.282
• Hs Code.: 2933990090
• European Community (EC) Number: 636-648-1
• UNII: TV437T5077
• DSSTox Substance ID: DTXSID00176577
• Nikkaji Number: J102.947I
• Wikipedia: 6-Hydroxymelatonin
• Wikidata: Q20707319
• Pharos Ligand ID: STNG3MMZX2NH
• Metabolomics Workbench ID: 38459
• ChEMBL ID: CHEMBL127421
• Mol file: 2208-41-5.mol

Synonyms:6-hydroxymelatonin;6-oxymelatonin

Chemical Property of 6-Hydroxymelatonin

Chemical Property:

• Vapor Pressure: 2.35E-13mmHg at 25°C
• Melting Point: 172-175oC
• Boiling Point: 564.7°Cat760mmHg
• PKA: 10.12±0.40(Predicted)
• Flash Point: 295.3°C
• PSA: 74.35000
• Density: 1.266g/cm³
• LogP: 1.95160
• Storage Temp.: Refrigerator
• Solubility.: alcohol: soluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 248.11609238
• Heavy Atom Count: 18
• Complexity: 298

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-HydroxyMelatonin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 22-40-51/53-20
• Safety Statements: 36/37-60

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)O
• Description: 6-hydroxy Melatonin is an active metabolite of melatonin . It is formed from melatonin by the cytochrome P450 (CYP) isoform CYP1A2 in human liver microsomes. 6-hydroxy Melatonin is a melatonin 1A (MT1A), MT1B, and MT2 receptor agonist. It inhibits dopamine release from isolated rabbit retina (IC50 = 0.0016 μM). 6-hydroxy Melatonin (10 and 100 μM) reduces increases in the levels of NF-κB, IL-6, and IL-8 and decreases in glutathione (GSH) levels in LPS- and peptidoglycan G-stimulated human umbilical vein endothelial cells (HUVECs) in an in vitro model of sepsis. It reduces iron-induced lipid oxidation in rat hippocampal homogenate when administered at a dose of 10 mg/kg.
• Uses: A major human metabolite of Melatonin 6-Hydroxymelatonin has been used as a melatonin derivative to test its protective effects in ultra violet B (UVB)-induced oxidative stress melanocytes and keratinocytes.

Technology Process of 6-Hydroxymelatonin

There total 8 articles about 6-Hydroxymelatonin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

6-acetoxy-3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester (519186-55-1) → 6-hydroxymelatonin (2208-41-5)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/S0040-4039(02)02763-6

Reference yield:

5-methoxy-N-acetyl-tryptamine (73-31-4) → 6-hydroxymelatonin (2208-41-5) + 5-methoxy-3-[2-(N-acetylamino)ethyl]indol-2(3H)-one (188397-16-2) + 4-hydroxymelatonin (39998-64-6) + 7,7'-bi(5-methoxy-N-acetyltryptamin-4-one)

Guidance literature:

With ferrous ammonium sulphate; edetate disodium; ascorbic acid; dihydrogen peroxide; In phosphate buffer; at 20 ℃; for 0.25h; pH=7.4; Further byproducts given;

DOI:10.1016/S0045-2068(02)00511-4

Reference yield:

5-methoxy-N-acetyl-tryptamine (73-31-4) → 6-hydroxymelatonin (2208-41-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / sodium hydroxide; tetrabutylammonium hydrogensulfate / CH₂Cl₂ / 1 h / 20 °C

2: 84 percent / aluminum chloride / 1,2-dichloro-ethane / 0.5 h / 20 °C

3: 83 percent / trifluoroacetic acid; m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 20 °C

4: 65 percent / NaOH / methanol

With sodium hydroxide; aluminium trichloride; tetra(n-butyl)ammonium hydrogensulfate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol; dichloromethane; 1,2-dichloro-ethane; 2: Friedel-Crafts acylation / 3: Baeyer-Villiger oxidation;

DOI:10.1016/S0040-4039(02)02763-6

upstream raw materials:

5-methoxy-N-acetyl-tryptamine

6-acetoxy-3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester

3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester

N-[2-(6-acetyl-1-carbethoxy-5-methoxyindol-3-yl) ethyl]acetamide

Refernces

• 1、 -. "Uses of melatonin in skin". Page/Page column 2; 7-9; sheet 2; sheet 6. . Retrieved 2008/06/13.
• 2、 Zhang, Houwen,Squadrito, Giuseppe L.,Uppu, Rao,Pryor, William A.. "Reaction of peroxynitrite with melatonin: A mechanistic study". . p. 526 - 534. Retrieved 2007/10/03.