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349720

(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
NACRES:
NA.22
PubChem Substance ID:
24861704
UNSPSC Code:
12352002
MDL number:
MFCD00274196
Assay:
98%
Form:
powder
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Quality Level

100

assay

98%

form

powder

reaction suitability

core: phosphonium, 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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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
View All Related Papers

Global Trade Item Number

SKUGTIN
349720-25G04061833424568
349720-100G04061833540596