Hexadecanoic acid,2,5-dioxo-1-pyrrolidinyl ester (14464-31-4)

The IUPAC name of Palmitic acid N-hydroxysuccinimide ester is (2,5-dioxopyrrolidin-1-yl) hexadecanoate. With the CAS registry number 14464-31-4, it is also named as Hexadecanoic acid,2,5-dioxo-1-pyrrolidinyl ester. The product's categories are various intermediates, intermediates and miscellaneous reagents. In addition, it is colourless shiny flakes, which should be stored at the temperature of -20 °C. Besides,  its molecular formula is C₂₀H₃₅NO₄ and molecular weight is 353.5.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 5.63; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.63; (4)ACD/LogD (pH 7.4): 5.63; (5)ACD/BCF (pH 5.5): 11241.71; (6)ACD/BCF (pH 7.4): 11241.71; (7)ACD/KOC (pH 5.5): 27616.9; (8)ACD/KOC (pH 7.4): 27616.9; (9)H bond acceptors: 5; (10)H bond donors: 0; (11)Freely Rotating Bonds: 16; (12)Polar Surface Area: 63.68 Å²; (13)Index of Refraction: 1.488; (14)Molar Refractivity: 98.58 cm³; (15)Molar Volume: 342 cm³; (16)Polarizability: 39.08×10^-24cm³ ; (17)Surface Tension: 40.7 dyne/cm; (18)Density: 1.03 g/cm³; (19)Flash Point: 224.2 °C; (20)Melting Point: 81 °C; (21)Enthalpy of Vaporization: 70.54 kJ/mol; (22)Boiling Point: 447.1 °C at 760 mmHg; (23)Vapour Pressure: 3.45E-08 mmHg at 25 °C.

Preparation of Palmitic acid N-hydroxysuccinimide ester: this chemical can be prepared by N-hydroxy-succinimide and Hexadecanoic acid.



This reaction needs Ethyl acetate and Dicyclohexylcarbodiimide. The yield is 83 %.

Uses of Palmitic acid N-hydroxysuccinimide ester: this chemical is used for the preparation of N-acylamino acids, aminoacyl-tRNA, coenzyme A, thioglycolic acid, ceramides, etc. It also can react with Glycine to get N-palmitoyl-glycine.



This reaction needs NaHCO₃, H₂O and Tetrahydrofuran at ambient temperature. The yield is 78 %.

People can use the following data to convert to the molecule structure.
(1)SMILES:O=C1N(OC(=O)CCCCCCCCCCCCCCC)C(=O)CC1
(2)InChI:InChI=1/C20H35NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(24)25-21-18(22)16-17-19(21)23/h2-17H2,1H3
(3)InChIKey:OTNHQVHEZCBZQU-UHFFFAOYAN
(4)Std. InChI:InChI=1S/C20H35NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(24)25-21-18(22)16-17-19(21)23/h2-17H2,1H3
(5)Std. InChIKey:OTNHQVHEZCBZQU-UHFFFAOYSA-N