2-[3-(3,3-dimethyl-1-octadecyl-2,3-dihydro-1H-indol-2-ylidene)prop-1-en-1-yl]-3,3-dimethyl-1-octadecyl-3H-indol-1-ium perchlorate

• ChemBase ID: 151170
• Molecular Formular: C59H97ClN2O4
• Molecular Mass: 933.86548
• Monoisotopic Mass: 932.71368727
• SMILES: CCCCCCCCCCCCCCCCCCN1c2ccccc2C(/C/1=C/C=C/C1=[N+](c2ccccc2C1(C)C)CCCCCCCCCCCCCCCCCC)(C)C.[O-][Cl](=O)(=O)=O
• Canonical SMILES: [O-][Cl](=O)(=O)=O.CCCCCCCCCCCCCCCCCCN1c2ccccc2C(/C/1=C/C=C/C1=[N+](CCCCCCCCCCCCCCCCCC)c2c(C1(C)C)cccc2)(C)C
• InChI: InChI=1S/C59H97N2.ClHO4/c1-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-41-50-60-54-46-39-37-44-52(54)58(3,4)56(60)48-43-49-57-59(5,6)53-45-38-40-47-55(53)61(57)51-42-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-2;2-1(3,4)5/h37-40,43-49H,7-36,41-42,50-51H2,1-6H3;(H,2,3,4,5)/q+1;/p-1
• InChIKey: JVXZRNYCRFIEGV-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[3-(3,3-dimethyl-1-octadecyl-2,3-dihydro-1H-indol-2-ylidene)prop-1-en-1-yl]-3,3-dimethyl-1-octadecyl-3H-indol-1-ium perchlorate
• IUPAC Traditional name: 2-[3-(3,3-dimethyl-1-octadecylindol-2-ylidene)prop-1-en-1-yl]-3,3-dimethyl-1-octadecylindol-1-ium perchlorate
• Synonyms: DiI; 1,1′-Dioctadecyl-3,3,3′,3′-tetramethylindocarbocyanine perchlorate

Database IDs

• CAS Number: 41085-99-8
• MDL Number: MFCD00142354
• Beilstein Number: 8251870
• PubChem SID: 24866515; 162245327; 24870519
• PubChem CID: 5706735

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 18.12517
• LogD (pH = 7.4): 18.12566
• Log P: 18.125666
• Molar Refractivity: 285.7715 cm^3
• Polarizability: 106.92843 Å^3
• Polar Surface Area: 6.25 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; methanol: soluble
• Melting Point: 68 °C (dec.)(lit.)
• Absorption Wavelength: λmax 549 nm
• Fluorescence: λex 550 nm; λem 567 nm in phosphate buffer/SDS pH 7.0

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC); 97%
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C59H97ClN2O4

DETAILS

Sigma Aldrich - 42364

Biochem/physiol Actions
Lipophilic carbocyanine dye used primarily for optical recordings of membrane voltage and for studies of membrane fluidity. Retrograde stain for neurons; provides intense, long-lasting staining of live neurons in vivo and in vitro.
Other Notes
Lipophilic fluorescent probe for studying membranes1,2

Sigma Aldrich - 468495

Biochem/physiol Actions
Lipophilic carbocyanine dye used primarily for optical recordings of membrane voltage and for studies of membrane fluidity. Retrograde stain for neurons; provides intense, long-lasting staining of live neurons in vivo and in vitro.
Packaging
100 mg in glass bottle