bis(2,5-dioxopyrrolidin-1-yl) octanedioate

• ChemBase ID: 127155
• Molecular Formular: C16H20N2O8
• Molecular Mass: 368.3386
• Monoisotopic Mass: 368.12196561
• SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCCCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCCCCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C16H20N2O8/c19-11-7-8-12(20)17(11)25-15(23)5-3-1-2-4-6-16(24)26-18-13(21)9-10-14(18)22/h1-10H2
• InChIKey: ZWIBGKZDAWNIFC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(2,5-dioxopyrrolidin-1-yl) octanedioate
• IUPAC Traditional name: disuccinimidyl suberate
• Synonyms: DSS; Suberic acid bis(N-hydroxysuccinimide ester); Disuccinimidyl suberate; Suberic acid bis(N-hydroxysuccinimide ester); Disuccinimidyl suberate; Disuccinimidyl octanedioate; Disuccinimidyl suberate (DSS); Suberic acid bis(N-hydroxysuccinimide ester); 双琥珀酰亚胺辛二酸酯; 双琥珀酰亚胺辛二酸酯; 辛二酸二琥珀酰亚胺酯 (DSS); 辛二酸双(N-羟基琥珀酰亚胺酯)

Database IDs

• CAS Number: 68528-80-3
• MDL Number: MFCD00049059
• PubChem SID: 24899500; 162221477
• PubChem CID: 100658
• Wikipedia Title: Disuccinimidyl_suberate

CALCULATED PROPERTIES

• Acid pKa: 17.408092
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.11896247
• LogD (pH = 7.4): 0.11896247
• Log P: 0.11896247
• Molar Refractivity: 83.0486 cm^3
• Polarizability: 33.16146 Å^3
• Polar Surface Area: 127.36 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: aqueous buffer: slightly soluble (may require 5-10% organic solvent in coupling mixture.); chloroform: soluble50 mg/mL; DMF: soluble
• Apperance: powder; Solid
• Melting Point: 166-170°C

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%; 97%
• Empirical Formula (Hill Notation): C16H20N2O8

DETAILS

Sigma Aldrich - S1885

Application
Homobifunctional cross-linking reagent with amine reactivity. Typically coupled to molecules containing primary amine by amide bond buffered at pH 7.5 (6.5-8.5). Incorporates 8-atom linker.
Packaging
1, 5 g in poly bottle
500 mg in poly bottle