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40227

Sigma-Aldrich

6-Dodecanoyl-N,N-dimethyl-2-naphthylamine

≥97.0% (HPLC), suitable for fluorescence

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Synonym(s):
2-(Dimethylamino)-6-dodecanoylnaphthalene, Laurdan, N,N-Dimethyl-6-dodecanoyl-2-naphthylamine
Empirical Formula (Hill Notation):
C24H35NO
CAS Number:
74515-25-6
Molecular Weight:
353.54
Beilstein:
7379104
MDL number:
MFCD00467560
PubChem Substance ID:
57649941
NACRES:
NA.32

Quality Level

100

Assay

≥97.0% (HPLC)

mp

88 °C (lit.)

solubility

DMF: soluble
acetonitrile: soluble
methanol: soluble

fluorescence

λex 366 nm; λem 497 nm in methanol

suitability

suitable for fluorescence

SMILES string

CCCCCCCCCCCC(=O)c1ccc2cc(ccc2c1)N(C)C

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

InChI key

JHDGGIDITFLRJY-UHFFFAOYSA-N

Related Categories

Application

6-Dodecanoyl-N,N-dimethyl-2-naphthylamine (Laurdan) is a fluorescent probe used to study membrane structure, order and dynamic processes such as fluidity.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Fluorescent membrane probe

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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    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What is the appearance of Product No. 40227 (6-Dodecanoyl-N,N-dimethyl-2-naphthylamine, also known as Laurdan)?

    Product 40227 (6-Dodecanoyl-N,N-dimethyl-2-naphthylamine) is described as powder to fine flakes.

  6. What is the solubility of Product No. 40227(6-Dodecanoyl-N,N-dimethyl-2-naphthylamine, also known as Laurdan)?

    Product 40227 (6-Dodecanoyl-N,N-dimethyl-2-naphthylamine) is soluble in N,N-dimethylformamide (DMF), methanol and acetonitrile.  It is also reported to be soluble in chloroform, according to Journal of Biological Chemistry, 248, 40186-40197 (2003).

  7. What are some of the physical properties of Product No. 40227 (6-Dodecanoyl-N,N-dimethyl-2-naphthylamine, also known as Laurdan)?

    The physical properties of  6-Dodecanoyl-N,N-dimethyl-2-naphthylamine are:Boiling Point: 497.4 °C at atmospheric pressure (760 mm Hg)Flash Point: 177.4 °CMelting Point: 88°C(lit.)Density: 0.987 g/cm3Vapor Pressure: 4.95-10 mm Hg at 25°CRefractive Index: 1.553

  8. What are the spectral properties (excitation and emission maxima) of 6-Dodecanoyl-N,N-dimethyl-2-naphthylamine, Laurdan, Product 40227?

    The spectral properties of 6-Dodecanoyl-N,N-dimethyl-2-naphthylamine are: ?ex 366 nm; ?em 497 nm in methanol.

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Keita Hayashi et al.
Colloids and surfaces. B, Biointerfaces, 87(1), 28-35 (2011-05-31)
The surface properties of Span 80 vesicles at various cholesterol contents, together with those of various liposomes, were characterized by using fluorescence probes. The membrane fluidity of the Span 80 vesicles was measured by 1,6-diphenyl-1.3.5-hexatriene (DPH) and trimethlyammonium-DPH (TMA-DPH), and
Adéla Melcrová et al.
Scientific reports, 6, 38035-38035 (2016-12-03)
Understanding interactions of calcium with lipid membranes at the molecular level is of great importance in light of their involvement in calcium signaling, association of proteins with cellular membranes, and membrane fusion. We quantify these interactions in detail by employing
Simmon Hofstetter et al.
Journal of microbiological methods, 91(1), 93-100 (2012-08-14)
A method for measuring the fluidity of inner membranes of populations of endospores of Clostridium spp. with a fluorescent dye was developed. Cells of Clostridium beijerinckii ATCC 8260 and Clostridium sporogenes ATCC 7955 were allowed to sporulate in the presence
L A Bagatolli et al.
Biochimica et biophysica acta, 1325(1), 80-90 (1997-04-03)
Laurdan (6-dodecanoyl-2-dimethylamine-naphthalene) is a fluorescent membrane probe of recent characterization. It was shown that this probe discriminates between phase transitions, phase fluctuations and the coexistence of phase domains in phospholipid multilamellar aggregates. We measured the excitation and emission generalized polarization
L.I. Hellgren
Plant Physiology and Biochemistry, 34, 455-455 (1996)
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