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Merck

L1881

1-Oleoyl-sn-glycero-3-phosphocholine

synthetic, ≥99%

Synonym(s):

(7R,18Z)-4,7-Dihydroxy-N,N,N-trimethyl-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-en-1-aminium 4-oxide, inner salt, 1-(9Z-Octadecenoyl)-sn-glycero-3-phosphocholine, 1-cis-9-Octadecenoyl-sn-glycero-3-phosphocholine, 1-Oleoyl-2-hydroxy-sn-glycerol-3-phosphocholine, 1-Oleoyl-sn-glycero-3-phosphorylcholine, 3-sn-Lysophosphatidylcholine, 1-oleoyl, L-γ-Oleoyl-α-lysolecithin, Lysolecithin, oleoyl, PC(18:1(9Z)/0:0), PC(18:1/0:0)

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About This Item

Empirical Formula (Hill Notation):
C26H52NO7P
CAS Number:
Molecular Weight:
521.67
UNSPSC Code:
12352211
NACRES:
NA.25
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4033747
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biological source

synthetic

Quality Level

assay

≥99%

form

powder

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(CCCCCCC/C=C\CCCCCCCC)=O

InChI

1S/C26H52NO7P/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/h12-13,25,28H,5-11,14-24H2,1-4H3/b13-12-/t25-/m1/s1

InChI key

YAMUFBLWGFFICM-PTGWMXDISA-N

Application

1-Oleoyl-sn-glycero-3-phosphocholine may be used as a reference for the analysis of lysolecithins extracted from tissues and cell membranes.


Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Gerd Schmitz et al.
Atherosclerosis, 208(1), 10-18 (2009-07-03)
Lysophosphatidylcholine (LPC) is a major plasma lipid that has been recognized as an important cell signalling molecule produced under physiological conditions by the action of phospholipase A(2) on phosphatidylcholine. LPC transports glycerophospholipid components such as fatty acids, phosphatidylglycerol and choline
B M Ross et al.
Journal of neurochemistry, 63(5), 1839-1848 (1994-11-01)
Lysophospholipids are generated during the turnover and breakdown of membrane phospholipids. We have identified and partially characterized three enzymes involved in the metabolism of lysophospholipids in human brain, namely, lysophospholipase, lysophospholipid:acyl-CoA acyltransferase (acyltransferase), and lysophospholipid:lysophospholipid transacylase (transacylase). Each enzyme displayed
Lynda M Foulds et al.
Biology of reproduction, 79(3), 525-536 (2008-05-30)
The ability of the gametes to escape detection by the immune system is vital to successful human reproduction. Furthermore, the observed capacity of the testis in some species to support tissue grafts without rejection (immunological privilege) indicates that spermatogenic cells