2,5-dioxopyrrolidin-1-yl 1-[2-({4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutanoyl}oxy)ethyl] butanedioate

• ChemBase ID: 104985
• Molecular Formular: C18H20N2O12
• Molecular Mass: 456.3576
• Monoisotopic Mass: 456.10162409
• SMILES: O=C(CCC(=O)ON1C(=O)CCC1=O)OCCOC(=O)CCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(CCC(=O)ON1C(=O)CCC1=O)OCCOC(=O)CCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C18H20N2O12/c21-11-1-2-12(22)19(11)31-17(27)7-5-15(25)29-9-10-30-16(26)6-8-18(28)32-20-13(23)3-4-14(20)24/h1-10H2
• InChIKey: QLHLYJHNOCILIT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 1-[2-({4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutanoyl}oxy)ethyl] butanedioate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 1-[2-({4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutanoyl}oxy)ethyl] butanedioate
• Synonyms: ETHYLENE GLYCOL bis(SUCCINIMIDYL SUCCINATE); Ethylene glycol-bis[succinimidyl succinate]; ETHYLENE GLYCOL-bis(SUCCINIC ACID N-HYDROXYSUCCINIMIDE ESTER); Di(N-succinimidyl) ethylene glycol disuccinate; EGS; Ethylene glycol bis(succinimidyl succinate); Ethylene glycol disuccinate di(N-succinimidyl) ester; Ethylene glycol-bis(succinic acid N-hydroxysuccinimide ester)

Database IDs

• CAS Number: 70539-42-3
• MDL Number: MFCD00049057
• Beilstein Number: 9167119
• PubChem SID: 24894501; 24886621; 162091818
• PubChem CID: 123663

CALCULATED PROPERTIES

• Acid pKa: 17.408009
• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): -1.937532
• LogD (pH = 7.4): -1.937532
• Log P: -1.937532
• Molar Refractivity: 95.7508 cm^3
• Polarizability: 38.677525 Å^3
• Polar Surface Area: 179.96 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetic acid: water (1:1): ≤50 mg/mL; DMF: soluble
• Apperance: powder

Safety Information

• Storage Condition: 2-8°C, Store Under Nitrogen
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥99.0% (CHN)
• Grade: purum
• Empirical Formula (Hill Notation): C18H20N2O12

DETAILS

MP Biomedicals - 05203394

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 73912

Other Notes
Cleavable crosslinking reagent for protein crosslinking and reversible immobilization1,2

Sigma Aldrich - E3257

Application
A homobifunctional, cleavable cross-linking reagent. Typically, coupled to molecules containing primary amines by amide bonds buffered at pH 7.5 (6.5-8.5). The linkage provides a 12-atom spacer.
Features and Benefits
The ethylene glycol linkage is cleavable by hydroxylamine.

REFERENCES

• Massague, J., Guillette, B.J. and Czech, M.P., J. Biol. Chem. , 256 : 2122 (1981).