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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)

Certificats d'analyse (COA)

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Sigma-Aldrich

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L-α-Lysophosphatidylcholine

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
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
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
Santosh Lamichhane et al.
Scientific data, 5, 180250-180250 (2018-11-14)
Early prediction and prevention of type 1 diabetes (T1D) are currently unmet medical needs. Previous metabolomics studies suggest that children who develop T1D are characterised by a distinct metabolic profile already detectable during infancy, prior to the onset of islet
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