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Dodecyltriphenylphosphonium bromide

Catalog Number
ACM15510551-1
Product Name
Dodecyltriphenylphosphonium bromide
Structure
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CAS
15510-55-1
  • Product Overview
  • Usage
Synonyms
(1-dodecyl)triphenylphosphonium bromide;n-Dodecyl triphenylphosphonium bromide;Lauryltriphenylphosphonium bromide
IUPAC Name
Dodecyl(triphenyl)phosphanium;bromide
Molecular Weight
511.52
Molecular Formula
C30H40BrP
Canonical SMILES
CCCCCCCCCCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
InChI
NSIFOGPAKNSGNW-UHFFFAOYSA-M
InChI Key
InChI=1S/C30H40P.BrH/c1-2-3-4-5-6-7-8-9-10-20-27-31(28-21-14-11-15-22-28,29-23-16-12-17-24-29)30-25-18-13-19-26-30;/h11-19,21-26H,2-10,20,27H2,1H3;1H/q+1;/p-1
Melting Point
85-88 °C(lit.)
Complexity
380
Covalently-Bonded Unit Count
2
EC Number
239-538-8
Exact Mass
510.205g/mol
H-Bond Acceptor
1
Heavy Atom Count
32
Monoisotopic Mass
510.205g/mol
Physical State
Solid
Rotatable Bond Count
14
Topological Polar Surface Area
0A^2
UNII
2OQV5UAF87
Application
Dodecyltriphenylphosphonium bromide is designed to target mitochondria and disrupt their function by inhibiting oxidative phosphorylation and shifting cell metabolism towards glycolysis. This compound is particularly effective in eradicating cancer stem cells, showing potency within the range of 50 nm to 1 mM, and does so with selectivity over normal cells. Furthermore, it enhances the efficacy of FDA-approved medications like doxycycline and niclosamide, as well as natural substances like berberine. Additionally, it preferentially inhibits the growth of Gram-positive bacteria compared to Gram-negative ones.
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