Succinimidyl Myristate Chemical Properties

Melting point:

80-81°C

Boiling point:

420.2±28.0 °C(Predicted)

Density 

1.05±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Off-White

Stability:

Moisture Sensitive

InChI

InChI=1S/C18H31NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-18(22)23-19-16(20)14-15-17(19)21/h2-15H2,1H3

InChIKey

NZEDHZOVUDEBGW-UHFFFAOYSA-N

SMILES

C(ON1C(=O)CCC1=O)(=O)CCCCCCCCCCCCC

CAS DataBase Reference

69888-86-4

Safety Information

HS Code 

2933.99.9701

Succinimidyl Myristate Usage And Synthesis

Chemical Properties

Colourless Leaflets

Uses

N-Succinimidyl Myristate is used to make cationic polysaccharide compositions for transfection

Uses

Succinimidyl Myristate is used to make cationic polysaccharide compositions for transfection.

Synthesis

Myristic acid (3.00 g, 13.1 mmol) and N,N'-dicyclohexylcarbodiimide (3.24 g, 15.7 mmol) were dissolved in 26.2 mL of anhydrous tetrahydrofuran and stirred at room temperature for 10 minutes. Subsequently, a solution of N-hydroxysuccinimide (1.81 g, 15.7 mmol) dissolved in 14.1 mL of the same solvent was added and the reaction mixture continued to be stirred for 22.5 h at room temperature. Complete conversion of the feedstock was confirmed by thin layer chromatographic analysis [CHCl3/MeOH (50:1, v/v)]. Upon completion of the reaction, insoluble material was removed by diafiltration. The solvent was removed by concentration under reduced pressure and the residue was recrystallized from ethanol containing traces of water to afford the target product 2,5-dioxopyrrolidin-1-yl tetradecanoate as a colorless solid (3.08 g, 72% yield). The product was characterized by 1H-NMR (300 MHz, CDCl3), 13C-NMR (75 MHz, CDCl3), EI-MS and elemental analysis (CHN), and the data were consistent with the expected structure.

References

[1] RSC Advances, 2015, vol. 5, # 81, p. 66339 - 66354
[2] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 2, p. 233 - 238
[3] Journal of Pharmacology and Experimental Therapeutics, 2004, vol. 309, # 1, p. 340 - 347
[4] Angewandte Chemie, 1996, vol. 108, # 15, p. 1791 - 1794
[5] Journal of Mass Spectrometry, 1995, vol. 30, # 6, p. 900 - 910

Succinimidyl Myristate(69888-86-4)Related Product Information

• BOLTON-HUNTER REAGENT
• N-SUCCINIMIDYLOXYCARBONYLPENTADECYL METHANETHIOSULFONATE
• PENTADECANOIC ACID N-HYDROXYSUCCINIMIDE ESTER
• 3-KETOPALMITIC ACID NHS ESTER
• SUCCINIMIDYL NERVONATE
• N-SUCCINIMIDYL PALMITATE
• Stearic acid-N-hydroxysuccinimide ester
• Succinimidyl Myristate