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Sigma-Aldrich

N,N,N-Trimethyl-4-(6-phenyl-1,3,5-hexatrien-1-yl)phenylammonium p-toluenesulfonate

BioReagent, suitable for fluorescence, ≥96.0% (TLC)

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Synonym(s):
1,6-Diphenyl-1,3,5-hexatriene-4′-trimethylammonium tosylate, 1-(4-Trimethylammoniophenyl)-6-phenyl-1,3,5-hexatriene p-toluenesulfonate, 4′-(Trimethylammonio)diphenylhexatriene p-toluenesulfonate, TMA-DPH
Linear Formula:
C21H24N · C7H7O3S
CAS Number:
Molecular Weight:
461.62
MDL number:
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

Quality Level

assay

≥96.0% (TLC)

form

powder

mp

237 °C (dec.) (lit.)

solubility

DMF: soluble
DMSO: soluble
methanol: soluble

fluorescence

λex 355 nm; λem ~430 nm in methanol
λex 355 nm; λem ~430 nm in methanol

suitability

suitable for fluorescence

SMILES string

Cc1ccc(cc1)S([O-])(=O)=O.C[N+](C)(C)c2ccc(\C=C\C=C\C=C\c3ccccc3)cc2

InChI

1S/C21H24N.C7H8O3S/c1-22(2,3)21-17-15-20(16-18-21)14-8-5-4-7-11-19-12-9-6-10-13-19;1-6-2-4-7(5-3-6)11(8,9)10/h4-18H,1-3H3;2-5H,1H3,(H,8,9,10)/q+1;/p-1/b5-4+,11-7+,14-8+;

InChI key

ZKARERKEBVSZCX-VMDDUYISSA-M

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Application

N,N,N-Trimethyl-4-(6-phenyl-1,3,5-hexatrien-1-yl)phenylammonium p-toluenesulfonate(TMA-DPH) is used as a fluorescence anisotropy probe in lipid membrane structural studies.

Other Notes

Probe for membrane fluidity

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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G Seydlová et al.
Folia microbiologica, 53(4), 303-307 (2008-09-02)
Processes occurring in the cytoplasmic membrane of the surfactin producer Bacillus subtilis were examined during a 3-d cultivation. The fatty acid composition was found to be almost stable within this interval, except for the early stationary phase when the nonbranched
P Gantet et al.
Plant physiology, 94(2), 729-737 (1990-10-01)
The blue emission anisotropy, r, of two lipophilic probes, diphenylhexatriene (DPH) and its trimethyl-ammonium derivative (TMA-DPH), has been measured in foliar Lupinus albus L. protoplasts for the first time by flow cytometry. Distinctive values have been obtained for protoplasts of
Jacek Grebowski et al.
Biochimica et biophysica acta, 1828(2), 241-248 (2012-09-20)
The influence of fullerenol on the activities of human erythrocyte membrane ATPases and the fluidity of the plasma membrane as well as the possibility of fullerenol incorporation into the plasma membrane were investigated. Fullerenol at concentrations up to 150 μg/mL
Maria Stasiuk et al.
FEBS letters, 582(25-26), 3607-3613 (2008-10-07)
The effects induced by natural phenolic and resorcinolic lipids on membrane permeability were investigated. All of the compounds tested perturbed the phospholipid bilayer and stabilized erythrocytes against hypoosmotically induced hemolysis. Dipalmitoylphosphatidylcholine liposomes with two preincorporated fluorescent dyes (1-(4-trimethylammoniumphenyl)-6-phenyl-1,3,5-hexatrien p-toluenesulfonate (TMA-DPH)
Eugenia Kovács et al.
Bioelectrochemistry (Amsterdam, Netherlands), 87, 230-235 (2012-04-24)
The interaction of positively-charged antibiotic gentamicin with cell membranes was studied to determine if any changes in membrane organization were induced by the drug. Opossum kidney epithelia (OK) cells were used as models of eukaryotic cells. Two methods were used:

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