Diphenylhexatriene

Last updated
Diphenylhexatriene [1]
Diphenylhexatriene.png
Diphenylhexatriene3D.png
Names
Preferred IUPAC name
1,1′-[(1E,3E,5E)-Hexa-1,3,5-triene-1,6-diyl]dibenzene
Other names
(1E,3E,5E)-1,6-Diphenylhexa-1,3,5-triene
[(1E,3E,5E)-6-Phenylhexa-1,3,5-trien-1-yl]benzene
trans,trans,trans-1,6-Diphenylhexatriene
Dicinnamyl
Identifiers
  • 17329-15-6 Yes check.svgY
3D model (JSmol)
ChEBI
ECHA InfoCard 100.015.465 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 217-011-3
PubChem CID
UNII
  • InChI=1S/C18H16/c1(5-11-17-13-7-3-8-14-17)2-6-12-18-15-9-4-10-16-18/h1-16H/b2-1+,11-5+,12-6+
    Key: BOBLSBAZCVBABY-WPWUJOAOSA-N
  • C1=CC=C(C=C1)/C=C/C=C/C=C/C2=CC=CC=C2
Properties
C18H16
Molar mass 232.326 g·mol−1
Melting point 199 to 203 °C (390 to 397 °F; 472 to 476 K)
-146.9·10−6 cm3/mol
Hazards
GHS classification and labelling: [2]
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Diphenylhexatriene is a fluorescent hydrocarbon used in the study of cell membranes. It is almost non-fluorescent in water, but it exhibits strong fluorescence when it is intercalated into lipid membranes. It incorporates itself into the lipid bilayer and acts like a lipid. [3] [4]

Related Research Articles

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Lipid Substance of biological origin that is soluble in nonpolar solvents

In biology and biochemistry, a lipid is a macro biomolecule that is soluble in nonpolar solvents. Non-polar solvents are typically hydrocarbons used to dissolve other naturally occurring hydrocarbon lipid molecules that do not dissolve in water, including fatty acids, waxes, sterols, fat-soluble vitamins, monoglycerides, diglycerides, triglycerides, and phospholipids.

<i>alpha</i>-Linolenic acid Chemical compound

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Lipid bilayer A thin polar membrane made of two layers of lipid molecules

The lipid bilayer is a thin polar membrane made of two layers of lipid molecules. These membranes are flat sheets that form a continuous barrier around all cells. The cell membranes of almost all organisms and many viruses are made of a lipid bilayer, as are the nuclear membrane surrounding the cell nucleus, and membranes of the membrane-bound organelles in the cell. The lipid bilayer is the barrier that keeps ions, proteins and other molecules where they are needed and prevents them from diffusing into areas where they should not be. Lipid bilayers are ideally suited to this role, even though they are only a few nanometers in width, because they are impermeable to most water-soluble (hydrophilic) molecules. Bilayers are particularly impermeable to ions, which allows cells to regulate salt concentrations and pH by transporting ions across their membranes using proteins called ion pumps.

Endosome Vacuole to which materials ingested by endocytosis are delivered

Endosomes are a collection of intracellular sorting organelles in eukaryotic cells. They are part of endocytic membrane transport pathway originating from the trans Golgi network. Molecules or ligands internalized from the plasma membrane can follow this pathway all the way to lysosomes for degradation or can be recycled back to the cell membrane in the endocytic cycle. Molecules are also transported to endosomes from the trans Golgi network and either continue to lysosomes or recycle back to the Golgi apparatus.

Lipid raft

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Sphingomyelin

Sphingomyelin is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath that surrounds some nerve cell axons. It usually consists of phosphocholine and ceramide, or a phosphoethanolamine head group; therefore, sphingomyelins can also be classified as sphingophospholipids. In humans, SPH represents ~85% of all sphingolipids, and typically make up 10–20 mol % of plasma membrane lipids.

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Nile red Chemical compound

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<i>alpha</i>-Parinaric acid Chemical compound

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Laurdan Chemical compound

Laurdan is an organic compound which is used as a fluorescent dye when applied to fluorescence microscopy. It is used to investigate membrane qualities of the phospholipid bilayers of cell membranes. One of its most important characteristics is its sensitivity to membrane phase transitions as well as other alterations to membrane fluidity such as the penetration of water.

In organic chemistry, octatetraene is a linear hydrocarbon consisting of a chain of eight carbon atoms linked by an alternating double-bond/single-bond pattern. The central two of the four alkene units can exhibit cis–trans isomerism, resulting in three isomers.

References

  1. 1,6-Diphenyl-1,3,5-hexatriene at Sigma-Aldrich
  2. "1,6-Diphenyl-1,3,5-hexatriene". pubchem.ncbi.nlm.nih.gov. Retrieved 13 December 2021.
  3. trans-trans-trans-1,6-Diphenyl-1,3,5-hexatriene Archived 2012-02-24 at the Wayback Machine , Molecule of the Week, American Chemical Society, December 8, 2008
  4. Litman, B; Barenholz, Y (1982). "[91] Fluorescent probe: Diphenylhexatriene". Biomembranes - Part H: Visual Pigments and Purple Membranes - I. Methods in Enzymology. 81. pp. 678–85. doi:10.1016/S0076-6879(82)81093-8. ISBN   978-0-12-181981-1. PMID   7098908.