4-carboxy-2-[6-(dimethylamino)-3-(dimethyliminiumyl)-3H-xanthen-9-yl]benzoate

• ChemBase ID: 155948
• Molecular Formular: C25H22N2O5
• Molecular Mass: 430.45258
• Monoisotopic Mass: 430.15287181
• SMILES: CN(C)c1ccc2c(c1)oc1cc(=[N+](C)C)ccc1c2c1cc(ccc1C(=O)[O-])C(=O)O
• Canonical SMILES: [O-]C(=O)c1ccc(cc1c1c2ccc(=[N+](C)C)cc2oc2c1ccc(c2)N(C)C)C(=O)O
• InChI: InChI=1S/C25H22N2O5/c1-26(2)15-6-9-18-21(12-15)32-22-13-16(27(3)4)7-10-19(22)23(18)20-11-14(24(28)29)5-8-17(20)25(30)31/h5-13H,1-4H3,(H-,28,29,30,31)
• InChIKey: COCMHKNAGZHBDZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-carboxy-2-[6-(dimethylamino)-3-(dimethyliminiumyl)-3H-xanthen-9-yl]benzoate
• IUPAC Traditional name: 4-carboxy-2-[3-(dimethylamino)-6-(dimethyliminio)xanthen-9-yl]benzoate
• Synonyms: 6-TAMRA; 6-Carboxytetramethylrhodamine

Database IDs

• CAS Number: 91809-67-5
• MDL Number: MFCD00467559
• PubChem SID: 24879252; 162250086
• PubChem CID: 2762604

CALCULATED PROPERTIES

• Acid pKa: 2.8407457
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.6117175
• LogD (pH = 7.4): -2.3560724
• Log P: -0.20115152
• Molar Refractivity: 157.019 cm^3
• Polarizability: 45.457 Å^3
• Polar Surface Area: 92.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; methanol: soluble
• Fluorescence: λex 543 nm; λem 575 nm in 0.1 M Tris pH 8.0

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥90% (HPLC)
• Suitability: suitable for fluorescence
• Description: single isomer
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C25H22N2O5

DETAILS

Sigma Aldrich - 55222

Application
The corresponding succinimidyl ester is a single isomer fluorophore most commonly used in automated DNA sequencing.