2,5-dioxopyrrolidin-1-yl dodecanoate

• ChemBase ID: 102866
• Molecular Formular: C16H27NO4
• Molecular Mass: 297.38988
• Monoisotopic Mass: 297.19400835
• SMILES: CCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: CCCCCCCCCCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-10-11-16(20)21-17-14(18)12-13-15(17)19/h2-13H2,1H3
• InChIKey: LRKGVVJOUNKTGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl dodecanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl dodecanoate
• Synonyms: Succinimidyl laurate; LAURIC ACID-N-HYDROXYSUCCINIMIDE ESTER; Lauric acid N-hydroxysuccinimide ester

Database IDs

• CAS Number: 14565-47-0
• MDL Number: MFCD00050401
• PubChem SID: 162091204; 24896358
• PubChem CID: 2802515

CALCULATED PROPERTIES

• Acid pKa: 17.709124
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.8478935
• LogD (pH = 7.4): 3.8478935
• Log P: 3.8478935
• Molar Refractivity: 79.2334 cm^3
• Polarizability: 31.542976 Å^3
• Polar Surface Area: 63.68 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ~98% (TLC)
• Empirical Formula (Hill Notation): C16H27NO4

DETAILS

MP Biomedicals - 02104817

Acetylating Agent

Sigma Aldrich - L3900

Biochem/physiol Actions
Lauric acid N-hydroxysuccinimide ester may be used for the synthesis of N-acylamino acids and lipidization of polypeptides or other applications that use N-hydroxysuccinimide ester conjugation chemistry.