2,5-Dioxopyrrolidin-1-yl palmitate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl palmitate
• CAS No.: 14464-31-4
• Molecular Formula: C20H35NO4
• Molecular Weight: 353.502
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID90404977
• Nikkaji Number: J348.393B
• Wikidata: Q72499447
• Mol file: 14464-31-4.mol

Synonyms:14464-31-4;N-Succinimidyl palmitate;2,5-Dioxopyrrolidin-1-yl palmitate;Palmitic acid N-hydroxysuccinimide ester;(2,5-dioxopyrrolidin-1-yl) Hexadecanoate;Hexadecanoic acid, 2,5-dioxo-1-pyrrolidinyl ester;N-palmitoyloxy-Succinimide;succinimidyl palmitate;2,5-Pyrrolidinedione, 1-[(1-oxohexadecyl)oxy]-;SCHEMBL337170;AMY4566;DTXSID90404977;OTNHQVHEZCBZQU-UHFFFAOYSA-N;MFCD00050402;ZB0998;AKOS024375430;CS-W011850;AC-32533;AS-55028;BP-28221;FT-0674723;W12504;A855544;J-007983;Palmitic acid N-hydroxysuccinimide ester, >=98% (TLC)

Chemical Property of 2,5-Dioxopyrrolidin-1-yl palmitate

Chemical Property:

• Appearance/Colour: colourless shiny flakes
• Vapor Pressure: 3.45E-08mmHg at 25°C
• Melting Point: 81 °C
• Refractive Index: 1.488
• Boiling Point: 447.1 °C at 760 mmHg
• Flash Point: 224.2 °C
• PSA: 63.68000
• Density: 1.03 g/cm³
• LogP: 5.01280
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 16
• Exact Mass: 353.25660860
• Heavy Atom Count: 25
• Complexity: 393

Purity/Quality:

98%Min ^*data from raw suppliers

N-SuccinimidylPalmitate ^*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: CCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
• Description: N-Succinimidyl palmitate is an intermidate for synthesis of lipid molecules. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules.
• Uses: N-hydroxysuccinimide ester of palmitic acid. Esters of N-hydroxysuccinimide have been used for the preparation of N-acylamino acids, aminoacyl-tRNA, coenzyme A, thioglycolic acid, ceramides, etc N-hydroxysuccinimide ester of palmitic acid. Esters of N-hydroxysuccinimide have been used for the preparation of N-acylamino acids, aminoacyl-tRNA, coenzyme A, thioglycolic acid, ceramides, etc.

Technology Process of 2,5-Dioxopyrrolidin-1-yl palmitate

There total 7 articles about 2,5-Dioxopyrrolidin-1-yl palmitate 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: 100.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + n-hexadecanoyl chloride (112-67-4) → palmitic acid N-succinimide ester (14464-31-4)

Guidance literature:

With triethylamine; In chloroform; at 20 ℃; for 8h; Cooling with ice;

Reference yield: 98.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 1-hexadecylcarboxylic acid (57-10-3) → palmitic acid N-succinimide ester (14464-31-4)

Guidance literature:

With dicyclohexyl-carbodiimide; In ethyl acetate; for 6h;

DOI:10.1039/c5ra10209j

Reference yield:

N-trifluoroacetoxy succinimide (5672-89-9) + 1-hexadecylcarboxylic acid (57-10-3) → palmitic acid N-succinimide ester (14464-31-4)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 0.666667h;

DOI:10.1134/S1068162019040034

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

1-hexadecylcarboxylic acid

Succinimide

n-hexadecanoyl chloride

Downstream raw materials:

N-n-hexadecanoyl (L)-alanine

(S)-α-Palmitoyl-N_ε-lysine

N-hexadecanoyl-L-aspartic acid

N-palmitoyl-L-serine

Refernces

• 1、 Burov,Yablokova,Dorosh,Shkarubskaya,Blank,Epstein,Fridkin. "Luliberin analogues exhibiting a cytotoxic effect on tumor cells in vitro". . p. 413 - 419. Retrieved 2006.
• 2、 Bonnet,Ollivier,Gras-Masse,Melnyk. "Chemoselective acylation of fully deprotected hydrazino acetyl peptides. Application to the synthesis of lipopeptides". . p. 443 - 449. Retrieved 2001.
• 3、 Guryanov, Ivan,Bondesan, Alex,Visentini, Dario,Orlandin, Andrea,Biondi, Barbara,Toniolo, Claudio,Formaggio, Fernando,Ricci, Antonio,Zanon, Jacopo,Cabri, Walter. "Innovative chemical synthesis and conformational hints on the lipopeptide liraglutide". . p. 471 - 479. Retrieved 2016.
• 4、 Sen, Shantanu,Singh, Prerana,Mishra, Narendra Kumar,Ganesh, Subramaniam,Sivakumar, Sri,Verma, Sandeep. "Blended polar/nonpolar peptide conjugate interferes with human insulin amyloid-mediated cytotoxicity". . . Retrieved 2021.
• 5、 -. "COMPOUNDS AND METHODS FOR THE TREATMENT OF DUCHENNE MUSCULAR DYSTROPHY". Paragraph 0439; 0443; 0495. . Retrieved 2021/06/04.
• 6、 -. "AN IMPROVED PROCESS FOR PREPARATION OF LIRAGLUTIDE". Page/Page column 11. . Retrieved 2021/07/02.