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Merck
CN

72335

9-(2,2-Dicyanovinyl)julolidine

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

Synonym(s):

9-Julolidinylmethylenemalononitrile, DCVJ

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About This Item

Empirical Formula (Hill Notation):
C16H15N3
CAS Number:
58293-56-4
Molecular Weight:
249.31
UNSPSC Code:
12352108
NACRES:
NA.32
PubChem Substance ID:
57652412
MDL number:
MFCD01747392
Beilstein/REAXYS Number:
413882

Key Documents

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InChI key

LROAUBRDKLVBCP-UHFFFAOYSA-N

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

product line

BioReagent

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

Quality Level

100

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN8251
BCCL9005
BCCK1334
BCCH1276
BCCC9453

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A Bhattacharyya et al.
Indian journal of biochemistry & biophysics, 32(6), 442-446 (1995-12-01)
Di(cyano vinyl)julolidine (DCVJ) is a fluorescent probe which has been used to monitor the local mobility of its binding sites on proteins. It shows a concentration dependence of its emission spectrum in water. At higher DCVJ concentrations, a longer wavelength
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
M A Haidekker et al.
American journal of physiology. Heart and circulatory physiology, 278(4), H1401-H1406 (2000-04-06)
Fluid shear stress (FSS) has been shown to be an ubiquitous stimulator of mammalian cell metabolism. Although many of the intracellular signal transduction pathways have been characterized, the primary mechanoreceptor for FSS remains unknown. One hypothesis is that the cytoplasmic
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
T Iio et al.
Journal of biochemistry, 109(4), 499-502 (1991-04-01)
A molecular rotor, 9-(dicyanovinyl)julolidine (DCVJ), is a fluorescent dye whose intramolecular rotation determines its fluorescence yield [Kung, C.E. & Reed, J.K. (1989) Biochemistry 28, 6678-6686]. DCVJ binds to bovine brain calmodulin and emits strong fluorescence. In fluorescence titration experiments, the
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