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72335

Sigma-Aldrich

9-(2,2-Dicyanovinyl)julolidine

BioReagent, suitable for fluorescence, ≥97.0% (HPLC)

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Synonym(s):
9-Julolidinylmethylenemalononitrile, DCVJ
Empirical Formula (Hill Notation):
C16H15N3
CAS Number:
Molecular Weight:
249.31
Beilstein:
413882
MDL number:
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

Quality Level

Assay

≥97.0% (HPLC)

form

crystals

solubility

DMSO: soluble
chloroform: soluble

fluorescence

λex 433 nm; λem 500 nm in 50 mM Tris pH 8.0; 40% glycerol

suitability

suitable for fluorescence

SMILES string

N#C\C(=C/c1cc2CCCN3CCCc(c1)c23)C#N

InChI

1S/C16H15N3/c17-10-13(11-18)7-12-8-14-3-1-5-19-6-2-4-15(9-12)16(14)19/h7-9H,1-6H2

Inchi Key

LROAUBRDKLVBCP-UHFFFAOYSA-N

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This Item
367992188872301
assay

≥97.0% (HPLC)

assay

≥98.0% (HPCE)

assay

≥90% (HPLC)

assay

≥97.0% (HPLC)

form

crystals

form

-

form

solid

form

solid

solubility

DMSO: soluble, chloroform: soluble

solubility

DMF: soluble, DMSO: soluble

solubility

DMF: soluble, DMSO: soluble

solubility

DMSO: soluble, chloroform: soluble

fluorescence

λex 433 nm; λem 500 nm in 50 mM Tris pH 8.0; 40% glycerol

fluorescence

λex 409 nm; λem 473 nm in 0.1 M Tris pH 9.0

fluorescence

λex 492 nm; λem 517 nm in 0.1 M Tris pH 8.0 (esterase)

fluorescence

λex 433 nm; λem 500 nm in 50 mM Tris pH 8.0; 40% glycerol

suitability

suitable for fluorescence

suitability

suitable for fluorescence

suitability

suitable for fluorescence

suitability

suitable for fluorescence

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Fluorescent probe for binding to proteins etc., quantum yield increases by decreasing free rotation; abs at ~450 nm, em at 480-505 nm (solvent dep.)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Dexter N Dean et al.
Biochemistry, 55(15), 2238-2250 (2016-03-26)
Oligomers of amyloid-β (Aβ) have emerged as the primary toxic agents responsible for early synaptic dysfunction and neuronal death in Alzheimer's disease (AD). Characterization of oligomers is an important step in the progress toward delineating the complex molecular mechanisms involved
Mark A Haidekker et al.
Bioorganic & medicinal chemistry, 10(11), 3627-3636 (2002-09-06)
Molecular rotors are fluorescent molecules with a viscosity-sensitive quantum yield that are often used to measure viscosity changes in cell membranes and liposomes. However, commercially available molecular rotors, such as DCVJ (1) do not localize in cell membranes but rapidly
Andrea Hawe et al.
Pharmaceutical research, 27(2), 314-326 (2009-12-31)
The aim was to evaluate fluorescent molecular rotors (DCVJ and CCVJ), which are mainly sensitive to viscosity, for the characterization of polysorbate-containing IgG formulations and compare them to the polarity-sensitive dyes ANS, Bis-ANS and Nile Red. IgG formulations with polysorbate
A Bhattacharya et al.
Protein science : a publication of the Protein Society, 5(10), 2029-2036 (1996-10-01)
9-(Dicyanovinyl) julolidine (DCVJ) is a fluorescent probe, which binds to a unique site on the tubulin dimer and exhibits different properties that are dependent upon its oligomeric state (Kung & Reed, 1989). DCVJ binds to tubulin, the tubulin-colchicine complex, and
James A Levitt et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 12(3), 662-672 (2011-02-18)
We present polarization-resolved fluorescence measurements of fluorescent molecular rotors 9-(2-carboxy-2-cyanovinyl)julolidine (CCVJ), 9-(2,2-dicyanovinyl)julolidine (DCVJ), and a meso-substituted boron dipyrromethene (BODIPY-C(12)). The photophysical properties of these molecules are highly dependent on the viscosity of the surrounding solvent. The relationship between their quantum

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