2,5-dioxopyrrolidin-1-yl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate

• ChemBase ID: 70719
• Molecular Formular: C14H16N2O6
• Molecular Mass: 308.28664
• Monoisotopic Mass: 308.10083624
• SMILES: C(=O)(CCCCCN1C(=O)C=CC1=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCCCCN1C(=O)C=CC1=O
• InChI: InChI=1S/C14H16N2O6/c17-10-5-6-11(18)15(10)9-3-1-2-4-14(21)22-16-12(19)7-8-13(16)20/h5-6H,1-4,7-9H2
• InChIKey: VLARLSIGSPVYHX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 6-(2,5-dioxopyrrol-1-yl)hexanoate
• Synonyms: N-Succinimidyl 6-maleimidohexanoate; 6-Maleimidocaproic acid N-succinimidyl ester; N-(ε-Maleimidocaproyloxy)succinimide; N-Succinimidyl 6-maleimidocaproate; EMCS; 6-Maleimidohexanoic acid N-hydroxysuccinimide ester; 6-马来酰亚氨基己酸 N-琥珀酰亚胺酯; N-(ε-马来酰亚胺己酰氧)琥珀酰亚胺; N-琥珀酰亚胺 6-马来酰亚胺己酸酯; 6-(马来酰亚胺基)己酸琥珀酰亚胺酯

Database IDs

• CAS Number: 55750-63-5
• MDL Number: MFCD00043043
• Beilstein Number: 1499815
• PubChem SID: 162036432; 24882444; 24880215
• PubChem CID: 5091655

CALCULATED PROPERTIES

• Acid pKa: 17.709124
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.1498469
• LogD (pH = 7.4): -0.1498469
• Log P: -0.1498469
• Molar Refractivity: 73.5429 cm^3
• Polarizability: 28.35547 Å^3
• Polar Surface Area: 101.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble100 mg/mL; DMF: soluble (lit.)
• Apperance: powder
• Melting Point: 67-73 °C; 70-73 °C(lit.)

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/37/38-40
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: false
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H351
• GHS Precautionary statements: P261-P281-P305 + P351 + P338; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%; ≥98.0% (HPLC); 95+%; 98%
• Empirical Formula (Hill Notation): C14H16N2O6

DETAILS

Sigma Aldrich - M9794

Application
A heterobifunctional cross-linking reagent incorporating an extended spacer with amine and sulfhydryl reactivity. Typically, coupled initially to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5) The second coupling is specific for molecules containing free sulfhydryl by thioether linkage buffered at pH 6.8 (6.5-7.0). Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates. Contains 9 atom linker. An extended aliphatic spacer stabilizes the maleimide prior to coupling compared to aromatic spacers.

Sigma Aldrich - 568600

Packaging
500 mg in glass bottle

Sigma Aldrich - 63177

Other Notes
Reagent for cross-linking and immobilisation of proteins1,2,3