N-benzoylphenylalanylphenylalinol acetate

Base Information

• Chemical Name: N-benzoylphenylalanylphenylalinol acetate
• CAS No.: 56121-42-7
• Molecular Formula: C₂₇H₂₈N₂O₄
• Molecular Weight: 444.53
• DSSTox Substance ID: DTXSID00893272
• Wikidata: Q104398742
• Mol file: 56121-42-7.mol

Synonyms:Benzenepropanamide,N-[1-[(acetyloxy)methyl]-2-phenylethyl]-a-(benzoylamino)-, [S-(R*,R*)]-; Asperglaucide;Aurantiamide acetate; Lyciumamide;O-Acetyl-N-(N'-benzoyl-L-phenylalanyl)-L-phenylalaninol; Sarapeptate;Saropeptate

Chemical Property of N-benzoylphenylalanylphenylalinol acetate

Chemical Property:

• Vapor Pressure: 2.35E-20mmHg at 25°C
• Boiling Point: 716.1°C at 760 mmHg
• Flash Point: 386.9°C
• PSA: 84.50000
• Density: 1.179g/cm³
• LogP: 4.10010
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 444.20490738
• Heavy Atom Count: 33
• Complexity: 620

Purity/Quality:

≥98% ^*data from raw suppliers

Asperglaucide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(CC1=CC=CC=C1)NC(=O)C(CC2=CC=CC=C2)NC(=O)C3=CC=CC=C3
• Isomeric SMILES: CC(=O)OC[C@H](CC1=CC=CC=C1)NC(=O)C(CC2=CC=CC=C2)NC(=O)C3=CC=CC=C3
• General Description: N-Benzoylphenylalanylphenylalinol acetate (also known as aurantiamide acetate) is a bioactive compound isolated from *Arisaema erubescens*, a plant used in traditional Chinese medicine. It has demonstrated potential as a non-toxic anticancer agent, particularly in studies involving K562 human leukemia cells, where it showed no cytotoxicity. N-benzoylphenylalanylphenylalinol acetate was successfully isolated and synthesized, with its structure confirmed through NMR analysis, supporting its further investigation for therapeutic applications.

Technology Process of N-benzoylphenylalanylphenylalinol acetate

There total 15 articles about N-benzoylphenylalanylphenylalinol acetate 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%

benzoyl chloride (98-88-4) + Acetic acid (S)-2-((S)-2-amino-3-phenyl-propionylamino)-3-phenyl-propyl ester; compound with trifluoro-acetic acid (138772-73-3) → aurantiamide acetate (80780-41-2,112924-28-4,125276-43-9,138812-57-4,139893-26-8,56121-42-7)

Guidance literature:

With triethylamine; In ethyl acetate; for 3h; Ambient temperature;

DOI:10.1016/0031-9422(91)80083-D

Reference yield: 87.0%

(S)-2-((S)-2-amino-3-phenylpropanamido)-3-phenylpropyl acetate + benzoyl chloride (98-88-4) → aurantiamide acetate (80780-41-2,112924-28-4,125276-43-9,138812-57-4,139893-26-8,56121-42-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

Reference yield: 83.0%

benzoyl chloride (98-88-4) + Acetic acid (R)-2-((R)-2-amino-3-phenyl-propionylamino)-3-phenyl-propyl ester; compound with trifluoro-acetic acid (138783-19-4) → asperglaucide (56121-42-7,80780-41-2,112924-28-4,125276-43-9,139893-26-8,138812-57-4)

Guidance literature:

With triethylamine; In ethyl acetate; for 3h; Ambient temperature;

DOI:10.1016/0031-9422(91)80083-D

upstream raw materials:

N-(N-benzoyl-L-phenylalanyl)-L-phenylalaninol

acetic anhydride

benzoyl chloride

Acetic acid (S)-2-((S)-2-amino-3-phenyl-propionylamino)-3-phenyl-propyl ester; compound with trifluoro-acetic acid

Downstream raw materials:

DL-N-benzoylphenylalanine

N-(N-benzoyl-L-phenylalanyl)-L-phenylalaninol

Refernces

Isolation of aurantiamide acetate from Arisaema erubescens

10.1055/s-2006-957878

The research focuses on the isolation and synthesis of aurantiamide acetate, a compound with potential anticancer properties, from the plant Arisaema erubescens, which is traditionally used in Chinese medicine. The purpose of the study was to identify the active agents responsible for the plant's anticancer effects. Through chromatographic separation of a methanol extract, aurantiamide acetate was isolated and its structure was confirmed by synthesis. The chemicals used in the process included methanol for extraction, hexane and chloroform for partitioning, and ethyl acetate as an eluent in chromatography. The conclusions of the research were that aurantiamide acetate was successfully isolated and synthesized, and its structure was confirmed by matching the NMR spectra of the synthetic product with that isolated from A. erubescens. Additionally, aurantiamide acetate was found to be non-toxic to K562 human leukemia cells, suggesting its potential as a safe anticancer agent.