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349720

Sigma-Aldrich

(3-Carboxypropyl)triphenylphosphonium bromide

98%

Synonym(s):

(4-Hydroxy-4-oxobutyl)triphenylphosphonium bromide

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About This Item

Linear Formula:
HO2C(CH2)3P(C6H5)3Br
CAS Number:
17857-14-6
Molecular Weight:
429.29
MDL number:
MFCD00274196
UNSPSC Code:
12352002
PubChem Substance ID:
24861704
NACRES:
NA.22

Assay

98%

reaction suitability

reaction type: C-C Bond Formation

mp

244-247 °C (lit.)

functional group

carboxylic acid
phosphine

SMILES string

[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

InChI key

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ7310
STBJ8668
STBF2050V
21706LH
14629KE

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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
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
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
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
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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