4-Methyl-DL-tryptophan

Base Information

• Chemical Name: 4-Methyl-DL-tryptophan
• CAS No.: 1954-45-6
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• Hs Code.: 2933990090
• European Community (EC) Number: 217-785-2
• NSC Number: 71048
• ChEMBL ID: CHEMBL563629
• Mol file: 1954-45-6.mol

Synonyms:4-Methyl-DL-tryptophan;1954-45-6;2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid;H-4-Me-DL-Trp-OH;EINECS 217-785-2;MFCD00055987;Tryptophan, 4-methyl-;4-Methyltryptophan #;H-Trp(4-Me)-OH;SCHEMBL109837;CHEMBL563629;SCHEMBL18028997;NSC71048;NSC 71048;NSC-71048;AKOS022926987;CS-W020502;DS-13334;SY263324;FT-0619080;DL-2-Amino-3-(4-methylindolyl)propionic acid;EN300-369975;F52887;M-5000;2-amino-3-(4-methyl-1H-indol-3-yl)propanoicacid;A934658;(2R)-2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid

Chemical Property of 4-Methyl-DL-tryptophan

Chemical Property:

• Boiling Point: 454.1 °C at 760 mmHg
• Flash Point: 228.4 °C
• PSA: 79.11000
• Density: 1.313 g/cm³
• LogP: 2.13100
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 270

Purity/Quality:

98%min ^*data from raw suppliers

4-Methyl-DL-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C2C(=CC=C1)NC=C2CC(C(=O)O)N
• Uses: 4-Methyl-DL-tryptophan?is used in preparation of Indolocarbazoles and related compounds as AP-70 kinase inhibitors.

Technology Process of 4-Methyl-DL-tryptophan

There total 7 articles about 4-Methyl-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: 85.0%

4-methyl-1H-indole (16096-32-5,261352-49-2) + serin (302-84-1,83245-15-2) → 2-amino-3-(4-methyl-1H-indol-3-yl)propionic acid (1954-45-6,33468-33-6,1139-73-7,141979-69-3)

Guidance literature:

With acetic anhydride; acetic acid; at 75 ℃; for 12h; Inert atmosphere;

Reference yield:

acetylamino-(4-methyl-indol-3-ylmethyl)-malonic acid → 2-amino-3-(4-methyl-1H-indol-3-yl)propionic acid (1954-45-6,33468-33-6,1139-73-7,141979-69-3)

Guidance literature:

With nitrogen; at 160 ℃; Erwaermen des Reaktionsprodukts mit Ba(OH)2 in H₂O;

DOI:10.1039/jr9480000705 DOI:10.1021/ja01104a028

Reference yield:

2-Formylamino-2-(4-methyl-1H-indol-3-ylmethyl)-malonic acid diethyl ester → 2-amino-3-(4-methyl-1H-indol-3-yl)propionic acid (1954-45-6,33468-33-6,1139-73-7,141979-69-3)

Guidance literature:

With sodium hydroxide; acetic acid; Yield given. Multistep reaction; 2.) heating;

DOI:10.1016/0040-4039(95)00001-S

upstream raw materials:

4-methyl-1H-indole

N,N-dimethyl-1-(4-methyl-1H-indol-3-yl)methanamine

N-(2,3-dimethylphenyl)formamide

acetylamino-(4-methyl-indol-3-ylmethyl)-malonic acid diethyl ester

Downstream raw materials:

(R)-2-amino-3-(4-methyl-1H-indol-3-yl)propanoic acid

Refernces

• 1、 Nettekoven, Matthias,Psiorz, Manfred,Waldmann, Herbert. "Synthesis of enantiomerically pure 4-alkylsubstituted tryptophan derivatives by a combination of organometallic reactions with enantioselective enzymatic transformations". . p. 1425 - 1428. Retrieved 2007/10/02.