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349720

Sigma-Aldrich

(3-Carboxypropyl)triphenylphosphonium bromide

98%

Synonyme(s) :

(4-Hydroxy-4-oxobutyl)triphenylphosphonium bromide

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About This Item

Formule linéaire :
HO2C(CH2)3P(C6H5)3Br
Numéro CAS:
17857-14-6
Poids moléculaire :
429.29
Numéro MDL:
MFCD00274196
Code UNSPSC :
12352002
ID de substance PubChem :
24861704
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

98%

Capacité de réaction

reaction type: C-C Bond Formation

Pf

244-247 °C (lit.)

Groupe fonctionnel

carboxylic acid
phosphine

Chaîne SMILES 

[Br-].OC(=O)CCC[P+](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C22H21O2P.BrH/c23-22(24)17-10-18-25(19-11-4-1-5-12-19,20-13-6-2-7-14-20)21-15-8-3-9-16-21;/h1-9,11-16H,10,17-18H2;1H

Clé InChI

NKVJKVMGJABKHV-UHFFFAOYSA-N

Application

Reactant for preparation of:
  • Piperamide analogs as histone deacetylase (HDAC) inhibitors with antitumor activity
  • Boron-containing benzoxaboroles as antimalarial agents
  • Methyl alkenyl quinolones as antimycobacterial agents
  • Solandelactone E via Sharpless epoxidation, Taber cyclopropanation, chemoselective reductions and lithiation-borylation-allylation sequence
  • Organotin compounds as antifungal agents
  • Oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B for negative regulation of insulin pathway (a promising target for treatment of diabetes and obesity)
  • 11-oxa prostaglandin analogs with ocular hypotensive activity

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
STBJ7310
STBJ8668
STBF2050V
21706LH
14629KE

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Min Han et al.
Molecular pharmaceutics, 11(8), 2640-2649 (2014-05-09)
In this study, doxorubicin (DOX) was conjugated to a lipophilic triphenylphosphonium (TPP) that is selectively taken up by the mitochondrial membrane of cells. This new derivative of DOX, i.e., TPP-DOX, was characterized by infrared spectroscopy (IR), nuclear magnetic resonance ((1)H
L Palanikumar et al.
Communications biology, 3(1), 95-95 (2020-03-05)
The practical application of nanoparticles (NPs) as chemotherapeutic drug delivery systems is often hampered by issues such as poor circulation stability and targeting inefficiency. Here, we have utilized a simple approach to prepare biocompatible and biodegradable pH-responsive hybrid NPs that
Xin-Cheng Zhong et al.
Pharmaceutical development and technology, 26(1), 21-29 (2020-10-20)
Multidrug resistance (MDR) is a serious challenge in chemotherapy and also a major threat to breast cancer treatment. As an intracellular energy factory, mitochondria provide energy for drug efflux and are deeply involved in multidrug resistance. Mitochondrial targeted delivery of
Niloufar Maghsoudnia et al.
Journal of drug targeting, 28(7-8), 818-830 (2020-05-27)
Many biological mechanisms including cellular metabolism and cell death are regulated by mitochondria known as powerhouse of the cell. Recently, let-7b, a tumour-suppressor microRNA has been detected in mitochondria of human cells targeting several mitochondrial-encoded respiratory chain genes. Triphenylphosphonium cation
Hongqiao Zhou et al.
Biomaterials science, 6(6), 1535-1545 (2018-04-20)
Although microwave (MW) thermal therapy has been widely studied for the treatment of tumors due to its less invasiveness, recurrence of tumors is still observed because of the relatively low bioavailability of MW sensitizers. For enhancing the bioavailability of MW
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