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253618

Sigma-Aldrich

Methyl 5-DOXYL-stearate, free radical

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

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About This Item

Empirical Formula (Hill Notation):
C23H45NO4
CAS Number:
38568-24-0
Molecular Weight:
399.61
MDL number:
MFCD00010543
UNSPSC Code:
12352000
PubChem Substance ID:
24855315
NACRES:
NA.22

Quality Level

100

functional group

ester
ether

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

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

141.8 °F - closed cup

Flash Point(C)

61 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR9246
MKBF5080
05122HC
07730CX

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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
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
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

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