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Merck
CN

263893

Phenoxazine

≥99%, purified by sublimation

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About This Item

Empirical Formula (Hill Notation):
C12H9NO
CAS Number:
135-67-1
Molecular Weight:
183.21
EC Number:
205-210-8
UNSPSC Code:
12352100
PubChem Substance ID:
24855892
Beilstein/REAXYS Number:
143234
MDL number:
MFCD00005014

Key Documents

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Product Name

Phenoxazine, ≥99%, purified by sublimation

InChI key

TZMSYXZUNZXBOL-UHFFFAOYSA-N

InChI

1S/C12H9NO/c1-3-7-11-9(5-1)13-10-6-2-4-8-12(10)14-11/h1-8,13H

SMILES string

N1c2ccccc2Oc3ccccc13

assay

≥99%

purified by

sublimation

mp

156-159 °C (lit.)

solubility

benzene: freely soluble(lit.)
chloroform: freely soluble(lit.)
diethyl ether: freely soluble(lit.)
ethanol: freely soluble(lit.)
petroleum ether: very slightly soluble(lit.)

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Application

Phenoxazine is a tricyclic 2′deoxycytidine analog that has been used to improve stacking interactions between heterocycles of oligonucleotide/RNA hybrids and to enhance cellular uptake.

General description

Phenoxazine dyes, including several Nile blue analogs, are known to localize selectively in animal tumors.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
00924MD
13727MU
18118DB
07505AG
06008EY

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C W Lin et al.
Cancer research, 51(4), 1109-1116 (1991-02-15)
The overall goal of our research is to develop effective new photosensitizers for tumor-selective photodynamic therapy. Phenoxazine dyes, including several Nile blue analogues, are known to localize selectively in animal tumors. Structural modifications yielded several series of analogues with substantially
W M Flanagan et al.
Nature biotechnology, 17(1), 48-52 (1999-01-27)
One of the major barriers to the development of antisense therapeutics has been their poor bioavailability. Numerous oligonucleotide modifications have been synthesized and evaluated for enhanced cellular permeation with limited success. Phenoxazine, a tricyclic 2' deoxycytidine analog, was designed to
Jinwei Ren et al.
Bioorganic & medicinal chemistry letters, 23(1), 301-304 (2012-11-21)
Five new phenoxazine-based alkaloids venezuelines A-E (1-5) and two new aminophenols venezuelines F-G (6-7), as well as three known analogues exfoliazone, chandrananimycin D and carboxyexfoliazone were isolated from the fermentation broth of the marine-derived bacterium Streptomyces venezuelae. The structures of
Martin Link et al.
Bioorganic & medicinal chemistry letters, 21(18), 5538-5542 (2011-08-02)
Novel amino-reactive phenoxazines were obtained by reasonably simple synthetic protocols and characterized in terms of their use as fluorescent labels for amines, amino acids and proteins in general. Purple labels (alternatives to Texas Red) and blue labels (alternatives to Cy-1)
Juozas Kulys et al.
Applied biochemistry and biotechnology, 158(2), 445-456 (2008-11-19)
Many industrial pollutants, xenobiotics, and industry-important compounds are known to be oxidized by peroxidases. It has been shown that highly efficient peroxidase substrates are able to enhance the oxidation of low reactive substrate by acting as mediators. To explore this
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