1-Methyl-DL-tryptophan

Base Information

• Chemical Name: 1-Methyl-DL-tryptophan
• CAS No.: 26988-72-7
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.255
• Hs Code.: 2933990090
• European Community (EC) Number: 248-157-6
• NSC Number: 721300,77678
• DSSTox Substance ID: DTXSID601314131
• Wikipedia: 1-Methyltryptophan
• Wikidata: Q4545793
• Metabolomics Workbench ID: 66129
• ChEMBL ID: CHEMBL513172
• Mol file: 26988-72-7.mol

Synonyms:1-methyl-DL-Trp;1-methyltryptophan;indoximod

Chemical Property of 1-Methyl-DL-tryptophan

Chemical Property:

• Melting Point: 250 °C
• Boiling Point: 429.3 °C at 760mmHg
• PKA: 2.26±0.10(Predicted)
• Flash Point: 213.4 °C
• PSA: 68.25000
• Density: 1.28 g/cm³
• LogP: 1.83300
• Storage Temp.: 2-8°C
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 218.105527694
• Heavy Atom Count: 16
• Complexity: 270

Purity/Quality:

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

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=CC=CC=C21)CC(C(=O)O)N
• Uses: 1-Methyltryptophan is a reagent that is used in the rational design of a minimalist multifunctional photo-immunotherapy nanoplatform toward boosting immunotherapy capability. 1-Methyl-DL-tryptophan, a competitive inhibitor of indoleamine 2,3 dioxygenase-1 (IDO1), has been used to study inflammation-induced depression in mice and syncytial virus induced bronchiolitis.

Technology Process of 1-Methyl-DL-tryptophan

There total 25 articles about 1-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: 92.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) + methyl iodide (74-88-4) → 1-methyl-L-tryptophan (21339-55-9,26988-72-7,110117-83-4)

Guidance literature:

L-Tryptophan; With iron(III) nitrate monohydrate; ammonia; sodium; at -60 ℃;

methyl iodide; In diethyl ether;

DOI:10.1021/jo802216z

Reference yield: 85.0%

N-tert-butyloxycarbonyl-L-1-methyltryptophan methyl ester → 1-methyl-L-tryptophan (21339-55-9,26988-72-7,110117-83-4)

Guidance literature:

With hydrogenchloride; In water; at 90 ℃; for 5h;

Reference yield:

1-methyl-α-N-acetyl-DL-tryptophan (732-10-5) → 2-amino-3-(1-methyl-1H-indol-3-yl)-propanoic acid (26988-72-7)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo01098a618

upstream raw materials:

3-(Dimethylaminomethyl)indole

ethyl 2-formamido-3-(3-indolyl)-2-carbethoxypropionate

acetylamino-(1-methyl-indol-3-ylmethyl)-malonic acid

acetylamino-indol-3-ylmethyl-malonic acid diethyl ester

Downstream raw materials:

N^α-(tert-butoxycarbonyl)-1-methyl-D-tryptophan

N^α-(tert-butoxycarbonyl)-1-methyl-L-tryptophan

Refernces

• 1、 -. "Method for synthesizing 1 - methyl - L L-tryptophan (by machine translation)". Paragraph 0008; 0009. . Retrieved 2020/08/02.
• 2、 Katayev, Dmitry,Larionov, Evgeny,Nakanishi, Masafumi,Besnard, Cline,Kündig, E. Peter. "Palladium-N-heterocyclic carbene (NHC)-catalyzed asymmetric synthesis of indolines through regiodivergent C(sp3)-H activation: Scope and DFT study". supporting information. p. 15021 - 15030. Retrieved 2015/02/19.