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L2131

Sigma-Aldrich

1-Stearoyl-sn-glycero-3-phosphocholine

≥99%, powder

Synonym(s):

L-α-Lysophosphatidylcholine, stearoyl, Lysolecithin, stearoyl

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About This Item

Empirical Formula (Hill Notation):
C26H54NO7P
CAS Number:
19420-57-6
Molecular Weight:
523.68
MDL number:
MFCD00050427
UNSPSC Code:
51191904
PubChem Substance ID:
24896302
NACRES:
NA.25

biological source

synthetic (organic)

assay

≥99%

form

powder

color

white

functional group

phospholipid

lipid type

phosphoglycerides

shipped in

ambient

storage temp.

−20°C

SMILES string

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)

InChI key

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>

Biochem/physiol Actions

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

62963

L-α-Lysophosphatidylcholine

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)
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