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Sigma-Aldrich

9-(2-Carboxy-2-cyanovinyl)julolidine

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

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Synonym(s):
9-([E]-2-Carboxy-2-cyanovinyl)julolidine, CCVJ
Empirical Formula (Hill Notation):
C16H16N2O2
CAS Number:
Molecular Weight:
268.31
MDL number:
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

Assay

≥97.0% (HPLC)

form

solid

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

OC(=O)\C(=C\c1cc2CCCN3CCCc(c1)c23)C#N

InChI

1S/C16H16N2O2/c17-10-14(16(19)20)9-11-7-12-3-1-5-18-6-2-4-13(8-11)15(12)18/h7-9H,1-6H2,(H,19,20)/b14-9+

InChI key

JXENNHTVELFRHV-NTEUORMPSA-N

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This Item
218887233521882
assay

≥97.0% (HPLC)

assay

≥90% (HPLC)

assay

≥97.0% (HPLC)

assay

≥95% (TLC)

form

solid

form

solid

form

crystals

form

solid

solubility

DMSO: soluble, chloroform: soluble

solubility

DMF: soluble, DMSO: soluble

solubility

DMSO: soluble, chloroform: soluble

solubility

DMF: soluble, DMSO: soluble, H2O: soluble (pH ≥ 5)

fluorescence

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

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

fluorescence

λex 504 nm; λem 529 nm in 0.1 M Tris pH 8.0

suitability

suitable for fluorescence

suitability

suitable for fluorescence

suitability

suitable for fluorescence

suitability

suitable for fluorescence

Application

Fluorescent probe for binding to proteins etc., quantum yield increases by decreasing free rotation: fluorescent molecular rotor.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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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Christopher Rumble et al.
The journal of physical chemistry. A, 116(44), 10786-10792 (2012-10-27)
The photochemistry of the rotor probe 9-(2-carboxy-2-cyanovinyl)julolidine (CCVJ) was studied to elucidate a curious effect of fluid flow previously reported. The apparent sensitivity to fluid motion observed in CCVJ but not in the closely related molecule 9-(dicyanovinyl)julolidine (DCVJ) is found
Elisabeth Ablinger et al.
International journal of pharmaceutics, 441(1-2), 255-260 (2012-12-04)
A differential scanning fluorimetry (DSF) based high-throughput screening assay with the fluorescent molecular rotor CCVJ (9-(2-carboxy-2-cyanovinyl)julolidine) was developed. CCVJ is mainly sensitive to viscosity and less to polarity in comparison to polarity-sensitive dyes like SYPRO Orange, which was commonly used
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
Xingyun Peng et al.
Carbohydrate polymers, 250, 116859-116859 (2020-10-15)
Fluorescence emissions of molecular rotors (MRs) are affected by local restrictions to molecular motion, and therefore it was considered that MRs can be used as structural probes of biopolymers. In this study, 9-(2-carboxy-2-cyanovinyl)-julolidine (CCVJ), a hydrophilic MR, was used to
Sagar Satpathi et al.
Organic & biomolecular chemistry, 17(21), 5392-5399 (2019-05-21)
Here, we have explored the light-up property of coumarin 343 (C343) selectively towards various i-motif DNAs based on the recognition of hemi-protonated cytosine-cytosine base pairing, unlike other DNA structures. We have also demonstrated the versatile ability of this i-motif ligand

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