N-Acetyl-DL-tryptophan

Base Information

• Chemical Name: N-Acetyl-DL-tryptophan
• CAS No.: 87-32-1
• Deprecated CAS: 10385-85-0
• Molecular Formula: C₁₃H₁₄N₂O₃
• Molecular Weight: 246.266
• Hs Code.: 29339990
• European Community (EC) Number: 201-739-3
• NSC Number: 90726,49124
• UNII: 4460NBV53F
• DSSTox Substance ID: DTXSID40861672
• Wikidata: Q27139225
• NCI Thesaurus Code: C77305
• RXCUI: 1368212
• Metabolomics Workbench ID: 103793
• ChEMBL ID: CHEMBL1905494
• Mol file: 87-32-1.mol

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

Chemical Property of N-Acetyl-DL-tryptophan

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.32E-14mmHg at 25°C
• Melting Point: 204-206 °C (dec.)(lit.)
• Refractive Index: 1.6450 (estimate)
• Boiling Point: 586.6 °C at 760 mmHg
• PKA: 3.65±0.10(Predicted)
• Flash Point: 308.6 °C
• PSA: 82.19000
• Density: 1.33 g/cm³
• LogP: 1.69060
• Storage Temp.: 2-8°C
• Solubility.: Slightly soluble in water, very soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.
• Water Solubility.: INSOLUBLE IN COLD WATER
• 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:

99.5% ^*data from raw suppliers

N-Acetyl-DL-tryptophan ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: CC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O
• Uses: N-Acetyl-DL-tryptophan is produced via chemical synthesis using the standard amino acid, tryptophan. It can be used in downstream applications of biopharmaceutical production as a transfer agent or stabilizer.

Technology Process of N-Acetyl-DL-tryptophan

There total 25 articles about N-Acetyl-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: 89.0%

tiolacetic acid (507-09-5) + Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7) → N-acetyl-DL-tryptophan (1218-34-4,87-32-1)

Guidance literature:

With copper(II)-grafted guanidine acetic acid-modified magnetite nanoparticles; In water; at 20 ℃; for 0.0833333h; chemoselective reaction; Green chemistry;

DOI:10.1002/aoc.3744

Reference yield: 73.0%

isopropylidene acetamido<(3-indolyl)methyl>malonate (82431-06-9) → N-acetyl-DL-tryptophan (1218-34-4,87-32-1)

Guidance literature:

With sodium carbonate; In ethanol; water; Heating;

DOI:10.1021/jo00140a038

Reference yield:

3-indolyl-2-acetylaminoprop-2-enoic acid (55629-73-7) → N-acetyl-DL-tryptophan (1218-34-4,87-32-1)

Guidance literature:

With acetic acid; zinc; at 50 ℃; for 4h; Temperature;

upstream raw materials:

indole

N-Acetamidoacrylic acid

acetic anhydride

acetylamino-indol-3-ylmethyl-malonic acid

Downstream raw materials:

(R,S)-α-(acetylamino)-N-(phenylmethyl)-1H-indole-3-propanamide

N-acetyl-N¹-nitrosotryptophan

L-Tryptophan

Nα-acetyl-N'-formylkynurenine

Refernces

• 1、 -. "Feed additive method for preparing DL-tryptophan". Paragraph 0027; 0035; 0036. . Retrieved 2016/10/07.
• 2、 Brahmbhatt, Keyur G.,Ahmed, Nafees,Sabde, Sudeep,Mitra, Debashis,Singh, Inder Pal,Bhutani, Kamlesh K.. "Synthesis and evaluation of β-carboline derivatives as inhibitors of human immunodeficiency virus". body text. p. 4416 - 4419. Retrieved 2010/09/18.