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263893

Sigma-Aldrich

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
Beilstein:
143234
EC Number:
205-210-8
MDL number:
MFCD00005014
UNSPSC Code:
12352100
PubChem Substance ID:
24855892

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.)

SMILES string

N1c2ccccc2Oc3ccccc13

InChI

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

InChI key

TZMSYXZUNZXBOL-UHFFFAOYSA-N

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General description

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

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.

Storage Class Code

13 - Non 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
Frédéric Bruyneel et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(33), 8283-8295 (2009-07-23)
Laccases are members of the blue copper oxidases family found in nature. They commonly oxidise a wide range of phenol and aniline derivatives, which in turn are involved in oxidative coupling reactions. Yet, laccases remain rarely described as biocatalysts in
Karina Mondragón-Vásquez et al.
Chemical communications (Cambridge, England), (44)(44), 6726-6728 (2009-11-04)
N(6)-(N'-Arylcarbamoyl)-2'-deoxyadenosine-H-phosphonates displayed molecular recognition towards cationic phenothiazinium and phenoxazinium dyes in aqueous solutions; studies have shown that binding is driven mainly by aromatic interactions and that size and shape-complementarity of the aromatic rings in host and guest provides selectivity.
Praew Thansandote et al.
The Journal of organic chemistry, 75(10), 3495-3498 (2010-04-29)
A rapid, four-step approach to alkyl- and aryl-substituted benzomorpholines is accomplished by a Pd-catalyzed domino C-C/C-N bond coupling using a norbornene template. Extension to phenoxazines and dihydrodibenzoxazepines is presented.
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