5-Methoxytryptophol

Base Information

• Chemical Name: 5-Methoxytryptophol
• CAS No.: 712-09-4
• Molecular Formula: C11H13 N O2
• Molecular Weight: 191.23
• Hs Code.: 2933990090
• European Community (EC) Number: 211-919-3
• DSSTox Substance ID: DTXSID00221394
• Nikkaji Number: J64.788H
• Wikidata: Q27162034
• Metabolomics Workbench ID: 37917
• ChEMBL ID: CHEMBL14485
• Mol file: 712-09-4.mol

Synonyms:5-methoxytryptophol;methoxytryptophol

Chemical Property of 5-Methoxytryptophol

Chemical Property:

• Appearance/Colour: White to off white powder
• Vapor Pressure: 6.55E-07mmHg at 25°C
• Refractive Index: 1.5220 (estimate)
• Boiling Point: 393.9 °C at 760 mmHg
• PKA: 14.90±0.10(Predicted)
• Flash Point: 192 °C
• PSA: 45.25000
• Density: 1.224 g/cm³
• LogP: 1.71130
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 186

Purity/Quality:

98% ^*data from raw suppliers

5-Methoxytryptophol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC=C2CCO
• Description: 5-methoxy Tryptophol (5-MTOH) is a natural indole that is produced by the pineal gland. It is a product of melatonin metabolism that may be biologically active. The levels of 5-MTOH in plasma vary in a diurnal pattern in rodents and humans.
• Uses: 5-Methoxytryptophol is a compound known to play a significant role in bone metabolism. 5-Methoxytryptophol can inhibit osteoclastogenesis and promote osteoblast differentiation.

Technology Process of 5-Methoxytryptophol

There total 17 articles about 5-Methoxytryptophol 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: 97.0%

5-methoxy-1H-indole-3-acetic acid (3471-31-6,142396-09-6) → 5-methoxytryptophol (712-09-4)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2h; Reflux; Inert atmosphere;

DOI:10.1002/anie.201610974

Reference yield: 92.0%

2,3-dihydro-2H-furan (1191-99-7,75454-45-4) + 4-Methoxyphenylhydrazine (3471-32-7) → 5-methoxytryptophol (712-09-4)

Guidance literature:

With L-(+)-tartaric acid-urea melt; at 70 ℃;

DOI:10.1021/ol302034r

Reference yield: 90.0%

2,3-dihydro-2H-furan (1191-99-7,75454-45-4) + 4-methoxyphenylhydrazine hydrochloride (19501-58-7) → 5-methoxytryptophol (712-09-4)

Guidance literature:

With sulfuric acid; In N,N-dimethyl acetamide; water; at 60 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.201803702

upstream raw materials:

(5-methoxy-1H-indol-3-yl)acetic acid ethyl ester

1-(tert-Butyldimethylsilyl)-3-(2-hydroxyethyl)-5-methoxyindole

2-ethoxytetrahydrofuran

4-methoxyphenylhydrazine hydrochloride

Downstream raw materials:

N,N-dimethyl-5-methoxytryptamine

4-chlorobenzoic acid 2-[5-methoxy-1H-indol-3-yl]ethyl ester

3-(2-chloroethyl)-5-methoxy-1H-3-indole

5-m-tolyl-oxazole-4-carboxylic acid {1-[2-(5-methoxy-1H-indol-3-yl)-ethyl]-1H-pyrazol-4-yl}-amide

Refernces

• 1、 Chen, Guzhou,Liu, Peng-Yu,Zou, Huanhuan,Hu, Jiadong,Fang, Xiaowu,Xu, Dongyang,He, Yu-Peng,Wei, Hongbo,Xie, Weiqing. "Au(I)-Catalyzed Domino Cyclization of 1,6-Diynes Incorporated with Indole". supporting information. p. 2279 - 2284. Retrieved 2021/04/05.
• 2、 Christoffers, Jens,Schmidtmann, Marc,Wachtendorf, Daniel. "Improved and Flexible Synthetic Access to the Spiroindole Backbone of Cebranopadol". supporting information. p. 6420 - 6423. Retrieved 2020/09/02.