Dodecyltriphenylphosphonium bromide Chemical Properties

Melting point:

85-88 °C(lit.)

storage temp. 

RT

solubility 

Soluble in DMSO (50 mg/ml) or ethanol (25 mg/mL)

form 

solid

color 

White

Sensitive 

Hygroscopic

BRN 

3581921

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

Cosmetics Ingredients Functions

ANTIMICROBIAL

CAS DataBase Reference

15510-55-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Dodecyltriphenylphosphonium bromide Usage And Synthesis

Application

Dodecyltriphenylphosphine bromide is a quaternary phosphine salt, which has a wide range of applications as a Wittig reagent, phase transfer catalyst, and surfactant. Quaternary phosphine salts are also a new generation of highly efficient, broad-spectrum, and low-toxicity bactericides, possessing not only strong bactericidal ability but also low foaming, strong slime-removing ability, and a wide applicable pH range. Dodecyltriphenylphosphine bromide exhibits good bactericidal effects against sulfate-reducing bacteria, but its bactericidal effect against heterotrophic bacteria is relatively poor. Dodecyltriphenylphosphine bromide can be prepared by reacting triphenylphosphine with 1-bromododecane.

Description

Dodecyl-TPP (15510-55-1) is a mitochondria-targeting agent which inhibits mitochondrial function inhibiting oxidative phosphorylation and shifting cell metabolism to glycolysis.1 Potently eradicates cancer stem cells (50 nm to 1 mM) selectively over normal cells1. Synergizes with FDA-approved drugs such as doxycycline and niclosamide as well as natural compounds such as berberine. Selectively inhibits the growth of Gram-positive over Gram-negative bacteria.2

Definition

ChEBI: An organic bromide salt that containing equal numbers of dodecyl(triphenyl)phosphonium cations and bromide anions.

Synthesis

26.2 g of triphenylphosphine, 24.9 g of 1-bromododecane and 30 ml of N,N-dimethylformamide were added to a three-necked flask equipped with a reflux condenser tube and heated to reflux under the protection of nitrogen, and the reaction was carried out. After 36h, the reaction was cooled and the solvent was evaporated under reduced pressure. The product was dissolved in 100 ml of water, extracted three times with 80 ml of n-hexane and dried in a vacuum drying oven to give a light yellow waxy solid, which was dissolved in . The solid was dissolved in 30 ml of ethyl acetate, precipitated with ether and filtered, 28.6 g of white waxy solid was obtained, the yield was 61.4%.

References

[1] nan

Dodecyltriphenylphosphonium bromide(15510-55-1)Related Product Information

• 1-Bromododecane
• Allyl bromide
• Dodecylbenzenesulphonic acid
• Triphenylphosphine hydrobromide
• Dimidium bromide
• Methyltriphenylphosphonium bromide
• tert-dodecylthiol
• Ammonium lauryl sulfate
• 1-Dodecanethiol
• Rocuronium bromide
• Ethidium bromide
• Sodium bromate
• 1-Dodecanol
• CALCIUM DODECYLBENZENE SULFONATE
• Vecuronium bromide
• Sodium lauroylsarcosinate
• Tetraphenylphosphonium bromide
• Methyl bromide