N,N-Dimethyl-6-propionyl-2-naphthylamine

Specifications

Purity

≥98% (HPLC)

Identity

1H-NMR

Appearance

Light yellow powder

Properties

Fluorescence

λex 361 nm, λem 498 nm in methanol

Melting Point

137 °C

Solvents

methanol, DMF, acetonitrile or acetone

Shipping

AMBIENT

Use / Stability

Stable for at least 2 years after receipt when stored at -20°C.

Handling Advice

Protect from light and moisture.

Long Term Storage

-20°C

Short Term Storage

+4°C

Transportation

Not dangerous goods

Description

N,N-dimethyl-6-propionyl-2-naphthylamine (prodan) has both an electron-donor and an electron-acceptor substituent, resulting in a large excited-state dipole moment and extensive solvent polarity-dependent fluorescence shifts. When prodan is incorporated into membranes, their fluorescence spectra are sensitive to the physical state of the surrounding phospholipids. In membranes, prodan appears to localize at the surface, although Fourier transform infrared measurements indicate some degree of penetration into the lipid interior. Excited-state relaxation of prodan is sensitive to the nature of the linkage between phospholipid hydrocarbon tails and the glycerol backbone. Tubulin and its hydrophobic surfaces have been probed with the enviroment-sensitive probes prodan. Prodan is also used for the generation of peroxy-oxalate chemiluminescence with H2O2.

InChi

InChI=1S/C15H17NO/c1-4-15(17)13-6-5-12-10-14(16(2)3)8-7-11(12)9-13/h5-10H,4H2,1-3H3

References

(1) B.A. Rowe et al.: J. Phys. Chem. B 110(30), 15021 (2006) , (2) E. Omanovic et al.: Int. J. Environm. Anal. Chem. 85(12-13), 853 (2005) , (3) M. Lin et al.: C. Huie: Anal. Chim. Acta 339(1-2), 131 (1997) , (4) A. Chakrabarti et al.: Biochem. Biophys. Res. Commun. 226, 495 (1996) , (5) P.L.G. Chong et al.: Biochemistry 28, 8358 (1989) , (6) P.L.G. Chong et al.: Biochemistry 27, 399 (1988)

InChi Key

MPPQGYCZBNURDG-UHFFFAOYSA-N

Smiles

CCC(=O)C1=CC2=CC=C(C=C2C=C1)N(C)C