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69888-86-4

69888-86-4 Structure

69888-86-4 Structure
IdentificationBack Directory
[Name]

Succinimidyl Myristate
[CAS]

69888-86-4
[Synonyms]

N-Succinimidyl Myristate
N-Succinimidyl Tetradecanoate
N-Hydroxysuccinimide myristate
Myristic acid N-hydroxysuccinimide ester
1-[(1-oxotetradecyl)oxy]-2,5-Pyrrolidinedione
Tetradecanoic acid N-hydroxysuccinimide ester
[Molecular Formula]

C18H31NO4
[MDL Number]

MFCD00522592
[MOL File]

69888-86-4.mol
[Molecular Weight]

325.44
Chemical PropertiesBack Directory
[Appearance]

Colourless Leaflets
[Melting point ]

80-81°C
[Boiling point ]

420.2±28.0 °C(Predicted)
[density ]

1.05±0.1 g/cm3(Predicted)
[storage temp. ]

Hygroscopic, -20°C Freezer, Under Inert Atmosphere
[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
Hazard InformationBack Directory
[Chemical Properties]

Colourless Leaflets
[Uses]

Used to make cationic polysaccharide compositions for transfection
[Synthesis]

N-Hydroxysuccinimide

6066-82-6

Myristic acid

544-63-8

Succinimidyl Myristate

69888-86-4

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
Safety DataBack Directory
[HS Code ]

2933.99.9701
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