5-Methoxy-dl-tryptophan

Base Information

• Chemical Name: 5-Methoxy-dl-tryptophan
• CAS No.: 28052-84-8
• Molecular Formula: C12H14 N2 O3
• Molecular Weight: 234.255
• Hs Code.: 29339900
• European Community (EC) Number: 248-800-0
• DSSTox Substance ID: DTXSID50862973
• Nikkaji Number: J2.700.659K
• ChEMBL ID: CHEMBL1491313
• Mol file: 28052-84-8.mol

Synonyms:5-Methoxy-dl-tryptophan;28052-84-8;2-amino-3-(5-methoxy-1H-indol-3-yl)propanoic acid;DL-5-Methoxytryptophan;DL-Tryptophan, 5-methoxy-;dl-5-Methoxy tryptophan;5-METHOXY-TRYPTOPHAN;EINECS 248-800-0;MFCD01074513;5_methoxy_tryptophan;5-Methoxytryptophan #;H-Trp(5-OMe)-OH;bmse000943;H-Trp(5-OCH3)-OH;SCHEMBL122600;H-D-Trp(5-OCH3)-OH;CHEMBL1491313;SCHEMBL18029115;KVNPSKDDJARYKK-UHFFFAOYSA-;DTXSID50862973;CHEBI:194846;MFCD00005650;AKOS005174050;NCGC00142448-01;NCGC00142448-02;LS-04225;SY258336;HY-128731;CS-0102497;FT-0620573;FT-0625409;EN300-258300;M-3570;A819304;5-Methoxy-DL-tryptophan, (SR)-2-Amino-3-(5-methoxyindolyl)propionic acid (H-DL-Trp(5-OMe)-OH)

Chemical Property of 5-Methoxy-dl-tryptophan

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 5.87E-10mmHg at 25°C
• Melting Point: 258-261 °C (dec.)(lit.)
• Refractive Index: 1.6660 (estimate)
• Boiling Point: 478.3°Cat760mmHg
• Flash Point: 243.1°C
• PSA: 88.34000
• Density: 1.347g/cm³
• LogP: 1.83120
• Storage Temp.: −20°C
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 234.10044231
• Heavy Atom Count: 17
• Complexity: 285

Purity/Quality:

98%, ^*data from raw suppliers

5-Methoxy-DL-tryptophan ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC=C2CC(C(=O)O)N
• Uses: 5-Methoxy-DL-tryptophan is a molecule produced by endothelial cells to modulate inflammatory responses and protect against systemic inflammation. It can also suppress lipopolysaccharide-induced inflammatory responses and signaling in macrophages and endotoxemic lung tissues.

Technology Process of 5-Methoxy-dl-tryptophan

There total 24 articles about 5-Methoxy-dl-tryptophan 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: 96.0%

5-methoxy-D-tryptophan methyl ester (89434-07-1,93299-35-5) → 5-methoxy-D-tryptophan (2504-22-5,25197-96-0,28052-84-8,89496-02-6,142436-28-0)

Guidance literature:

With sodium hydroxide; In methanol;

Reference yield: 83.0%

5-methoxy-L-tryptophan methyl ester (89434-07-1,93299-35-5) → 5-methoxy-L-tryptophan (2504-22-5,25197-96-0,28052-84-8,89496-02-6,142436-28-0)

Guidance literature:

With sodium hydroxide; In methanol;

Reference yield: 76.0%

Nα-acetyl-5-methoxy-L-tryptophan (67010-09-7,114926-33-9) → 5-methoxy-L-tryptophan (2504-22-5,25197-96-0,28052-84-8,89496-02-6,142436-28-0)

Guidance literature:

With sodium hydroxide; cobalt(II) chloride; In water; at 37 ℃; for 48h; acylase, pH=7.0;

upstream raw materials:

5-methoxy-D-tryptophan methyl ester

5-trifluoroacetoxy-N_b-methoxycarbonyl-D-tryptophan methyl ester

3-(1H-Indol-3-yl)-2-methoxycarbonylamino-propionic acid methyl ester

3-(5-Hydroxy-1H-indol-3-yl)-2-methoxycarbonylamino-propionic acid methyl ester

Downstream raw materials:

2-Amino-3-(5-methoxy-1H-indol-3-yl)-propionic acid

2-((tert-butoxycarbonyl)amino)-3-(5-methoxy-1H-indol-3-yl)propanoic acid

cecilin

2-amino-3-(5-methoxy-indol-3-yl)-propan-1-ol

Refernces

• 1、 Irie, Kunihiko,Ishida, Akihiko,Nakamura, Tohru,Oh-ishi, Tokuro. "Syntheses of Substituted L- and D-Tryptophans". . p. 2126 - 2139. Retrieved 2007/10/02.