Laurdan

Specifications

Purity

≥97% (HPLC)

Appearance

Light yellow solid

Identity

1H-NMR

Properties

Solvents

methanol, DMF, acetonitrile, chloroform

Melting Point

88 °C (lit.)

Fluorescence

λex 366 nm, λem 497 nm in methanol

Documentation

Safety Data Sheet (SDS)

CDX D0098 MSDS.pdf

Shipping

AMBIENT

Short Term Storage

+4°C

Long Term Storage

-20°C

Handling Advice

Protect from light and moisture.

Use / Stability

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

Transportation

Not dangerous goods

Description

N,N-Dimethyl-6-dodecanoyl-2-naphthylamine (Laurdan) is used as an environmentally sensitive probe for the labeling of plasma membranes. The lauroyl-sidechain integrates into the hydrophobic core of biological membranes, the polar fluorescent moiety is at level of the glycerol-backbone. Dipolar relaxation processes of the naphtylamine-moiety with neighboring polar molecules lead to wavelength-shifts of the emission-spectra. The physical state of the membrane and effects of temperature, cholesterol or ethanol on various membrane-systems have been monitored.

Smiles

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

InChi Key

JHDGGIDITFLRJY-UHFFFAOYSA-N

References

(1) S.S. Antollini et al.: Meth. Mol. Biol. 400, 531 (2007) , (2) Y.L. Zhang et al.: Biochem. Biophys. Res. Comm. 347(3), 838 (2006) , (3) L. Bagatolli et al.: Biochimica et Biophysica Acta 1325, 80 (1997) , (4) L.I. Hellgren et al.: Plant Physiol. Biochem. 34(4), 455 (1996) , (5) G. Weber et al.: Biochemistry 18(14), 3075 (1979)

InChi

InChI=1S/C24H35NO/c1-4-5-6-7-8-9-10-11-12-13-24(26)22-15-14-21-19-23(25(2)3)17-16-20(21)18-22/h14-19H,4-13H2,1-3H3