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72335

Sigma-Aldrich

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
Beilstein:
413882
MDL number:
MFCD01747392
UNSPSC Code:
12352108
PubChem Substance ID:
57652412
NACRES:
NA.32

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

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

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

Certificates of Analysis (COA)

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Markus J Schmidt et al.
Journal of biological engineering, 11, 24-24 (2017-08-09)
The molecular rotor 9-(2-Carboxy-2-cyanovinyl)julolidine (CCVJ) is presumed to have a sensitivity towards velocity or shear which is supposed to result in a change in fluorescence quantum yield. Furthermore, a previously reported photoisomeric behavior may contribute to the measured fluorescence intensity
Christian Lubich et al.
Pharmaceutical research, 32(9), 2863-2876 (2015-03-20)
Sub-visible particles were shown to facilitate unwanted immunogenicity of protein therapeutics. To understand the root cause of this phenomenon, a comprehensive analysis of these particles is required. We aimed at establishing a flow-cytometry-based technology to analyze the amount, size distribution
T Furuno et al.
Immunology letters, 33(3), 285-288 (1992-08-01)
A confocal fluorescence microscope was used to study the exocytotic secretory processes of mast cells in combination with an fluorescent molecular rotor, 9-(dicyanovinyl)julolidine (DCVJ). DCVJ is known to be an unique fluorescent dye which increases its quantum yield with decreasing
C E Kung et al.
Biochemistry, 28(16), 6678-6686 (1989-08-08)
9-(Dicyanovinyl)julolidine (DCVJ) is a fluorescent dye whose intramolecular rotational relaxation is solvent dependent. Since its quantum yield increases with decreasing free volume, this molecule has been very useful in monitoring synthetic polymer reactions and measuring local microviscosity changes in phospholipid
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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