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157945

(4-Carboxybutyl)triphenylphosphonium bromide

98%

Synonym(s):

5-(Triphenylphosphonio)pentanoic acid bromide, Carboxybutyltriphenylphosphonium bromide, NSC 147756

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About This Item

Linear Formula:
(C6H5)3P(Br)(CH2)4COOH
CAS Number:
17814-85-6
Molecular Weight:
443.31
UNSPSC Code:
12352107
NACRES:
NA.22
PubChem Substance ID:
24849711
EC Number:
241-782-5
Beilstein/REAXYS Number:
3586477
MDL number:
MFCD00011906
Assay:
98%
Form:
powder
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Quality Level

200

assay

98%

form

powder

reaction suitability

core: phosphonium, reaction type: C-C Bond Formation

mp

204-207 °C (lit.)

functional group

carboxylic acid, phosphine

SMILES string

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

InChI

1S/C23H23O2P.BrH/c24-23(25)18-10-11-19-26(20-12-4-1-5-13-20,21-14-6-2-7-15-21)22-16-8-3-9-17-22;/h1-9,12-17H,10-11,18-19H2;1H

InChI key

MLOSJPZSZWUDSK-UHFFFAOYSA-N

Application

  • Used as a platform for delivery of pro-apoptotic peptides into the mitochondria of tumor cells

Reactant for preparation of:
  • Ring skeletons via ring closing metathesis and double bond migration ring closing metathesis reactions
  • Methyl alkenyl quinolones as antimycobacterial agents
  • Prostaglandins and their drug analogs via Gold-catalyzed Meyer-Schuster rearrangement
  • Diphenylmethylpiperazines as N-type calcium channel blockers as potential therapeutic agents
  • Folate receptor-specific glycinamide ribonucleotide formyltransferase (GARFTase) inhibitors with antitumor activity
  • Cycloalkylidene alkanols with antileishmanial activity, via Wittig reaction

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pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

hcodes

H301,H318

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

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
SDBB3104
0000356493
0000356494
0000356495
0000356495

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Sabah Haq et al.
OncoTargets and therapy, 10, 2427-2447 (2017-05-13)
Prostaspheres-based three dimensional (3D) culture models have provided insight into prostate cancer (PCa) biology, highlighting the importance of cell-cell interactions and the extracellular matrix (EMC) in the tumor microenvironment. Although these 3D classical spheroid platforms provide a significant advance over
Raquel Palao-Suay et al.
Journal of materials science. Materials in medicine, 28(10), 152-152 (2017-09-02)
Active targeting not only of a specific cell but also a specific organelle maximizes the therapeutic activity minimizing adverse side effects in healthy tissues. The present work describes the synthesis, characterization, and in vitro biological activity of active targeting nanoparticles (NP)
Gantumur Battogtokh et al.
Nanomedicine : nanotechnology, biology, and medicine, 13(2), 733-743 (2016-11-07)
The objective of this study was to develop a mitochondria-targeted photosensitizer (PS) for photodynamic therapy (PDT). Herein, a porphyrin-derivative photosensitizer, pheophorbide-a (PheoA), was conjugated to carboxybutyltriphenylphosphonium (TPP) via a carbodiimide linkage to enhance mitochondrial targeting and TPP-PheoA conjugate was further
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Global Trade Item Number

SKUGTIN
157945-50G04061833448540
157945-250G04061833440049