2,5-dioxopyrrolidin-1-yl hexadecanoate

• ChemBase ID: 102676
• Molecular Formular: C20H35NO4
• Molecular Mass: 353.4962
• Monoisotopic Mass: 353.25660861
• SMILES: CCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
• 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
• InChIKey: OTNHQVHEZCBZQU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl hexadecanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl hexadecanoate
• Synonyms: N-(Palmitoyloxy)succinimide; N-Succinimidyl palmitate; Palmitic acid N-succinimidyl ester; PALMITIC ACID-N-HYDROXYSUCCINIMIDE ESTER; Palmitic acid N-hydroxysuccinimide ester; Palmitic Acid N-hydroxysuccinimide Ester; 2,5-Dioxo-1-pyrrolidinyl Ester Hexadecanoic Acid; N-Succinimidyl Palmitate

Database IDs

• CAS Number: 14464-31-4
• MDL Number: MFCD00050402
• Beilstein Number: 1547411
• PubChem SID: 24898166; 162088494
• PubChem CID: 4620598

CALCULATED PROPERTIES

• Acid pKa: 17.709124
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.6261683
• LogD (pH = 7.4): 5.6261683
• Log P: 5.6261683
• Molar Refractivity: 97.6374 cm^3
• Polarizability: 38.89 Å^3
• Polar Surface Area: 63.68 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; THF
• Apperance: White Shiny Flakes
• Melting Point: 87-88°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive; Store in Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C20H35NO4

DETAILS

MP Biomedicals - 02102556

Acetylating Agent

Sigma Aldrich - P1162

Application
Useful in the synthesis of hexadecanoyl derivatives of amino- and thio-compounds such as amino acids, aminoacyl-tRNA, coenzyme A, thioglycolic acid, etc.

Toronto Research Chemicals - S691400

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.

REFERENCES

• Lapidot, Y., et al.: J. Lipid Res., 8, 142 (1967)
• Lapidot, Y., et al.: Biochim. Biophys. Acta, 145, 292 (1967)
• Al-Arif, A., et al.: J. Lipid Res., 10, 344 (1967)
• Ong, D.E., and Brady, R.N., J. Lipid Res., 13, 819 (1972)