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253618

Sigma-Aldrich

Methyl 5-DOXYL-stearate, free radical

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Synonym(s):
2-(4-Methoxy-4-oxobutyl)-4,4-dimethyl-2-tridecyl-3-oxazolidinyloxy, 2-(4-Methoxy-4-oxobutyl)-4,4-dimethyl-2-tridecyl-3-oxazolidinyloxy, free radical, 5-MeSL
Empirical Formula (Hill Notation):
C23H45NO4
CAS Number:
Molecular Weight:
399.61
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

storage temp.

2-8°C

SMILES string

CCCCCCCCCCCCCC1(CCCC(=O)OC)OCC(C)(C)N1[O]

InChI

1S/C23H44NO4/c1-5-6-7-8-9-10-11-12-13-14-15-18-23(19-16-17-21(25)27-4)24(26)22(2,3)20-28-23/h5-20H2,1-4H3

InChI key

XKWHHWBOJRTEHX-UHFFFAOYSA-N

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vibrant-m

163945

4-Amino-TEMPO, free radical

vibrant-m

257494

3-Cyano-PROXYL

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

General description

Spin label

Application

Reactant free radical spin label involved in:
  • Synthesis of alkyl phospholipid analogs of perifosine and miltefosine for cytotoxicity studies
  • Studies of micellular properties via electron spin (paramagnetic) resonance
  • Spin-labeled stearates partitioning into the lipid domain of stratum corneum
  • Location determinations in sodium dodecyl sulfate micelles
  • Studies of local mobility and structure of micelles via its use as a probe
  • ESR (EPR) studies of metalloporphyrin intercalation into liposome membranes

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

141.8 °F - closed cup

flash_point_c

61 °C - closed cup


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M L Bianconi et al.
Biochemical and biophysical research communications, 152(1), 344-350 (1988-04-15)
ESR spectra of membrane spin probes are conventionally used to obtain structural information. Here we show, for the first time, that when a membrane-soluble compound undergoes a chemical reaction, time-dependent changes in the ESR spectra of membrane spin probes can
Catarina Pereira-Leite et al.
Physical chemistry chemical physics : PCCP, 20(21), 14398-14409 (2018-05-18)
Gastrointestinal (GI) toxicity is a major drawback of the chronic use of nonsteroidal anti-inflammatory drugs (NSAIDs). The NSAIDs topical actions on the protective phospholipid layers of the GI mucosa seem to be a central toxicity mechanism of these pharmaceuticals. This
Nataly Lebedeva et al.
The journal of physical chemistry. B, 110(20), 9791-9799 (2006-05-19)
A strategy to locate spectroscopic probes in micelles is presented which involves establishing a "benchmark" probe, i.e., one whose position is well-known and against which other probe positions may be established. Theoretically calculated values of the fraction of the micelle

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