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L2131

Sigma-Aldrich

1-Stearoyl-sn-glycero-3-phosphocholine

≥99%, powder

Synonyme(s) :

L-α-Lysophosphatidylcholine, stearoyl, Lysolecithin, stearoyl

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About This Item

Formule empirique (notation de Hill):
C26H54NO7P
Numéro CAS:
19420-57-6
Poids moléculaire :
523.68
Numéro MDL:
MFCD00050427
Code UNSPSC :
51191904
ID de substance PubChem :
24896302
Nomenclature NACRES :
NA.25

Source biologique

synthetic (organic)

Pureté

≥99%

Forme

powder

Couleur

white

Groupe fonctionnel

phospholipid

Type de lipide

phosphoglycerides

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

O[C@](COP([O-])(OCC[N+](C)(C)C)=O)([H])COC(CCCCCCCCCCCCCCCCC)=O

InChI

1S/C26H55NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3,(H,30,31)

Clé InChI

ARQYPVZFUYHQFR-UHFFFAOYSA-N

Application

<ul>
<li><strong>Plant-derived phenolics inhibit the accrual of structurally characterised protein and lipid oxidative modifications: </strong> Demonstrates the role of 1-Stearoyl-sn-glycero-3-phosphocholine in preventing oxidative modifications in cellular membranes, pertinent to drug delivery systems and cell signaling studies (Soler-Cantero et al., 2012).</li>
</ul>

Actions biochimiques/physiologiques

1-Stearoyl-sn-glycero-3-phosphocholine (LPC, Lyso-PC) is used in the development of drug transdermal delivery devices such as liposomes and micelles. It inhibits histone deacetylase 3 (HDAC3) activity and signal transducer and activator of transcription 3 (STAT3) phosphorylation and exhibits anticancer activity in chronic myelogenous leukemia (CML) K562 cells.
1-Stearoyl-sn-glycero-3-phosphocholine (LPC, Lyso-PC) is used in the development of drug transdermal delivery devices such as liposomes and micelles.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Asako Katsume et al.
Arteriosclerosis, thrombosis, and vascular biology, 31(5), 1084-1092 (2011-03-05)
Reactive oxygen species (ROS) are involved in the initial process of atherosclerosis, whereas it remains to be determined how atherogenic stimulus causes ROS-mediated proinflammatory reactions. Here, we focused on proline-rich tyrosine kinase (PYK2)-mediated ROS generation and examined how atherogenic stimulus
Ji Hoon Jung et al.
Cell biochemistry and biophysics, 67(3), 1379-1389 (2013-06-04)
We here investigated the anticancer mechanism of 1-stearoyl-sn-glycero-3-phosphocholine (LPC), one of the lysophosphatidylcholines, in chronic myelogenous leukemia (CML) K562 cells. LPC significantly showed cytotoxicity at 80 μM and induced apoptosis by sub-G1 accumulation, increase in Annexin V positive and caspase
Michał Flasiński et al.
Journal of colloid and interface science, 348(2), 511-521 (2010-05-25)
The interactions of beta-CD with one component monolayers of cholesterol (chol), 1-stearoyl-sn-glycero-3-phosphocholine (lyso-PC), 1,2-dipalmitpyl-sn-phosphocholine (DPPC), sphingomyelin (SM) and the SM/chol and DPPC/chol mixtures have been investigated by the Langmuir monolayer technique and the synchrotron grazing incidence X-ray diffraction (GIXD). The
Marcus O W Grimm et al.
Journal of chromatography. A, 1218(42), 7713-7722 (2011-08-30)
Alzheimer's disease (AD) is a devastating neurodegenerative disorder characterized by extracellular senile plaques mainly consisting of Aβ, a 40-42 amino acid long peptide, and intracellular neurofibrillary tangles, accompanied by an excessive loss of synapses. Recently evidence accumulated that nutrition, especially
Jongwon Shim et al.
International journal of pharmaceutics, 388(1-2), 251-256 (2010-01-12)
We have studied how the transdermal delivery of lidocaine hydrochloride (LHC) is affected by the morphology of lipid carriers, liposomes and micelles, having the same lipid composition of 1-stearoyl-sn-glycero-3-phosphocholine (LPC) and cholesteryl hemisuccinate (CHEMS). In vitro drug permeation study, carried
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