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253596

Sigma-Aldrich

16-DOXYL-stearic acid, free radical

Synonym(s):

16-SASL, 16DOXYL, 16NS, 2-(14-Carboxytetradecyl)-2-ethyl-4,4-dimethyl-3-oxazolidinyloxy, free radical

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About This Item

Empirical Formula (Hill Notation):
C22H42NO4
CAS Number:
53034-38-1
Molecular Weight:
384.57
MDL number:
MFCD00010066
UNSPSC Code:
12352106
PubChem Substance ID:
24855314
NACRES:
NA.22

form

solid

mp

47-55 °C (lit.)

storage temp.

2-8°C

SMILES string

CCC1(CCCCCCCCCCCCCCC(O)=O)OCC(C)(C)N1[O]

InChI

1S/C22H42NO4/c1-4-22(23(26)21(2,3)19-27-22)18-16-14-12-10-8-6-5-7-9-11-13-15-17-20(24)25/h4-19H2,1-3H3,(H,24,25)

InChI key

RPAZYIOIDZRJOO-UHFFFAOYSA-N

Application

Involved in membrane studies including:
  • Dynamics and state of lipid bilayer-internal water using 1H dynamic nuclear polarization
  • Distribution of fatty acids
  • Transversal relaxation of nitroxides for PELDOR Spectroscopy
  • Effects of different lipid components on detergent-resistant membranes
Spin label for membrane fluidity studies.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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N Rapoport et al.
Archives of biochemistry and biophysics, 384(1), 100-108 (2001-01-09)
To assess the effect of a polymeric surfactant, Pluronic P-105 on the activity of electron transport chains in the mitochondria of HL-60 cells, the bioreduction rates of two membrane-localized lipophilic spin probes, 16-doxylstearic acid methyl ester (16-DSME) and 5-doxylstearic acid
X Qi et al.
Circulation, 104(13), 1544-1549 (2001-09-26)
The maintenance and termination of reentry arrhythmias are determined by tissue properties such as refractoriness and conduction velocity. Although the effects of Na(+) and K(+) channel block on electrophysiological properties and defibrillation threshold (DFT) have been studied, little is known
M A Baqué et al.
Biochemical and biophysical research communications, 505(4), 1038-1042 (2018-10-13)
Different spin labels were incorporated to the membranes of cultured insect UFL-AG-286 cells in order to characterize their physical properties by Electron Paramagnetic Resonance spectroscopy (EPR). The spectrum of the spin label 12-SASL incorporated to cell membranes was similar as those
Gábor Balogh et al.
PloS one, 6(6), e21182-e21182 (2011-06-24)
Cellular membranes respond rapidly to various environmental perturbations. Previously we showed that modulations in membrane fluidity achieved by heat stress (HS) resulted in pronounced membrane organization alterations which could be intimately linked to the expression and cellular distribution of heat
P V Dubovskii et al.
Journal of molecular biology, 305(1), 137-149 (2000-12-15)
Carditoxins (CTXs) from cobra snake venoms, the basic 60-62 residue all-beta sheet polypeptides, are known to bind to and impair the function of cell membranes. To assess the membrane induced conformation and orientation of CTXs, the interaction of the P-type
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