N-Acetyl-L-tryptophan

Base Information

• Chemical Name: N-Acetyl-L-tryptophan
• CAS No.: 1218-34-4
• Molecular Formula: C13H14N2O3
• Molecular Weight: 246.266
• Hs Code.: 29339900
• European Community (EC) Number: 214-935-9
• UNII: U9264T8OAE
• DSSTox Substance ID: DTXSID10883669
• Nikkaji Number: J61.737G
• Wikidata: Q27144794
• NCI Thesaurus Code: C77305
• RXCUI: 1368212
• Metabolomics Workbench ID: 87144
• ChEMBL ID: CHEMBL54170
• Mol file: 1218-34-4.mol

Synonyms:acetyltryptophan;N-acetyl-D-tryptophan;N-acetyltryptophan;N-acetyltryptophanate sodium

Chemical Property of N-Acetyl-L-tryptophan

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 1.32E-14mmHg at 25°C
• Melting Point: 186 °C
• Refractive Index: 1.645
• Boiling Point: 586.6 °C at 760 mmHg
• PKA: 3.65±0.10(Predicted)
• Flash Point: 308.6 °C
• PSA: 82.19000
• Density: 1.33g/cm3
• LogP: 1.69060
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 246.10044231
• Heavy Atom Count: 18
• Complexity: 332

Purity/Quality:

99% ^*data from raw suppliers

N-Acetyl-L-Tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)O
• Uses: N-Acetyl-L-Tryptophan, is a derivative of L-Tryptophan (T947210), that can be used as competitive inhibitor to identify and characterize tryptophanases. It can also be used as an NK1 tachykinin receptor antagonist, that may help to develop a novel therapeutic intervention for the treatment of reperfusion injury in acute ischemic stroke.

Technology Process of N-Acetyl-L-tryptophan

There total 50 articles about N-Acetyl-L-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: 99.0%

N-acetyltryptophan methyl ester (2824-57-9,16108-06-8,36060-94-3) → N-AcTrp (1218-34-4) + AcTrpOMe (2824-57-9,16108-06-8,36060-94-3)

Guidance literature:

With sodium hydroxide; phosphate buffer; pronase EC 3.4.24.4; In tetrahydrofuran; Ambient temperature;

Reference yield: 80.0%

acetyl chloride (75-36-5) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-AcTrp (1218-34-4)

Guidance literature:

With sodium hydroxide; In acetone; at 20 ℃; pH=> 10;

DOI:10.1016/j.bmc.2014.08.035

Reference yield: 76.0%

tiolacetic acid (507-09-5) + L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-AcTrp (1218-34-4)

Guidance literature:

tiolacetic acid; With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

L-Tryptophan; With 2,4-Dinitrofluorobenzene; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1002/anie.200805782

upstream raw materials:

tetrachloromethane

acetic anhydride

L-Tryptophan

N-acetyl-DL-tryptophan

Downstream raw materials:

N-acetyl-L-tryptophane ethyl ester

D,L-1-Methyl-3,4-dihydro-β-carboline-3-carboxylic acid

L-Tryptophan

acetyltryptophan ethylester

Refernces

• 1、 Oversby. "-". . p. 1393. Retrieved 1958.
• 2、 Mueller, Karsten,Korth, Hans-Gert,De Groot, Herbert,Kirsch, Michael. "Reaction of vitamin e compounds with n-nitrosated tryptophan derivatives and its analytical use". . p. 7532 - 7542. Retrieved 2007.
• 3、 Huang,Niemann. "-". . p. 1541,1547. Retrieved 1951.
• 4、 Shabica,Tishler. "-". . p. 3251. Retrieved 1949.
• 5、 Castro, Albino,Iglesias, Emilia,Leis, J. Ramon,Pena, M. Elena,Tato, Jose Vazquez,Williams, D. Lyn H.. "Kinetics and Mechanism of the Nitrosation of N-Acetyltryptophan and of the Denitrosation of N-Acetyl-N1-nitrosotryptophan". . p. 1165 - 1168. Retrieved 1986.
• 6、 Peissker, Fabian,Fischer, Lutz. "Crosslinking of imprinted proteases to maintain a tailor-made substrate selectivity in aqueous solutions". . p. 2231 - 2237. Retrieved 1999.
• 7、 Cativiela, Carlos,Mayoral, Jose A.,Melendez, Enrique,Oro, Luis A.,Pinillos, Maria T.,Uson, Rafael. "Influence of the Hetercyclic Ring on the Asymmetric Synthesis of β-Hetarylalanines by Homogeneous Catalytic Hydrogenation". . p. 2502 - 2504. Retrieved 1984.
• 8、 Kwon, Hongmok,Ha, Hyunsoo,Jeon, Hayoung,Jang, Jaebong,Son, Sang-Hyun,Lee, Kiho,Park, Song-Kyu,Byun, Youngjoo. "Structure-activity relationship studies of dipeptide-based hepsin inhibitors with Arg bioisosteres". supporting information. . Retrieved 2020/12/25.
• 9、 Kochetova,Kustova,Kuritsyn. "Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media". . p. 80 - 85. Retrieved 2018/03/09.