2,5-dioxopyrrolidin-1-yl 3',6'-bis(dimethylamino)-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylate

• ChemBase ID: 131765
• Molecular Formular: C29H25N3O7
• Molecular Mass: 527.5247
• Monoisotopic Mass: 527.16925016
• SMILES: CN(C)c1ccc2c(c1)Oc1cc(ccc1C12c2ccc(cc2C(=O)O1)C(=O)ON1C(=O)CCC1=O)N(C)C
• Canonical SMILES: O=C1CCC(=O)N1OC(=O)c1ccc2c(c1)C(=O)OC12c2ccc(cc2Oc2c1ccc(c2)N(C)C)N(C)C
• InChI: InChI=1S/C29H25N3O7/c1-30(2)17-6-9-21-23(14-17)37-24-15-18(31(3)4)7-10-22(24)29(21)20-8-5-16(13-19(20)28(36)38-29)27(35)39-32-25(33)11-12-26(32)34/h5-10,13-15H,11-12H2,1-4H3
• InChIKey: CXYYHBMOVJJZTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 3',6'-bis(dimethylamino)-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthene]-5-carboxylate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 3',6'-bis(dimethylamino)-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxylate
• Synonyms: 5(6)-Carboxytetramethylrhodamine N-hydroxysuccinimide ester; 5(6)-Carboxytetramethylrhodamine N-succinimidyl ester

Database IDs

• CAS Number: 150408-83-6
• MDL Number: MFCD00077324
• Beilstein Number: 8739319
• PubChem SID: 162226042; 24853135; 24892720
• PubChem CID: 12142572

CALCULATED PROPERTIES

• Acid pKa: 17.69729
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.9230657
• LogD (pH = 7.4): 3.9306326
• Log P: 3.9307294
• Molar Refractivity: 143.9255 cm^3
• Polarizability: 53.386314 Å^3
• Polar Surface Area: 105.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble; DMF: soluble; methanol: soluble
• Fluorescence: λex 543 nm; λem 576 nm in methanol; λex 554 nm; λem 584 nm in 0.1 M phosphate pH 8.0

Safety Information

• 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: ≥70% (coupling to amines); ≥90%
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C29H25N3O7

DETAILS

Sigma Aldrich - 21955

Other Notes
Rhodamine derived label for amine modification and protein conjugation1,2