sodium 3-{2-[4-(1,3-dibutyl-4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)but-2-en-1-ylidene]-2,3-dihydro-1,3-benzoxazol-3-yl}propane-1-sulfonate

• ChemBase ID: 147678
• Molecular Formular: C26H32N3NaO6S2
• Molecular Mass: 569.66855
• Monoisotopic Mass: 569.16302204
• SMILES: CCCCN1C(=O)C(=C/C=C/C=c\2/n(c3ccccc3o2)CCCS(=O)(=O)[O-])C(=O)N(C1=S)CCCC.[Na+]
• Canonical SMILES: CCCCN1C(=O)C(=C/C=C/C=c/2\oc3c(n2CCCS(=O)(=O)[O-])cccc3)C(=O)N(C1=S)CCCC.[Na+]
• InChI: InChI=1S/C26H33N3O6S2.Na/c1-3-5-16-28-24(30)20(25(31)29(26(28)36)17-6-4-2)12-7-10-15-23-27(18-11-19-37(32,33)34)21-13-8-9-14-22(21)35-23;/h7-10,12-15H,3-6,11,16-19H2,1-2H3,(H,32,33,34);/q;+1/p-1
• InChIKey: OSQUFVVXNRMSHL-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 3-{2-[4-(1,3-dibutyl-4,6-dioxo-2-sulfanylidene-1,3-diazinan-5-ylidene)but-2-en-1-ylidene]-2,3-dihydro-1,3-benzoxazol-3-yl}propane-1-sulfonate
• IUPAC Traditional name: sodium merocyanine 540(1-)
• Synonyms: Merocyanine 540; 部花青 540

Database IDs

• CAS Number: 62796-23-0
• MDL Number: MFCD00013438
• Beilstein Number: 3585252
• PubChem SID: 162241865; 24859412; 24882975
• PubChem CID: 5702743

CALCULATED PROPERTIES

• Acid pKa: -0.8852447
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 2.5114522
• LogD (pH = 7.4): 2.5114112
• Log P: 4.8878093
• Molar Refractivity: 158.6348 cm^3
• Polarizability: 57.175312 Å^3
• Polar Surface Area: 110.29 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: alcohols: soluble; DMSO: soluble; H2O: soluble
• Melting Point: 285 °C (dec.)(lit.)
• Absorption Wavelength: λmax 555 nm
• Fluorescence: λex 555 nm; λem 578 nm in methanol

Safety Information

• RTECS: DM4866500
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (HPLC)
• Grade: for fluorescence
• Compostion: Dye content, 90%
• Empirical Formula (Hill Notation): C26H32N3NaO6S2

DETAILS

Sigma Aldrich - 323756

Packaging
100 mg in glass bottle
Application
Fluorescent axonal stain.1

Sigma Aldrich - 63876

Other Notes
Sensitive probe for membrane potential1,2,3; Selective staining of immature hemopoietic cells in flow cytometry4; Review5