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L1881

Sigma-Aldrich

1-Oleoyl-sn-glycero-3-phosphocholine

synthetic, ≥99%

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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)
Empirical Formula (Hill Notation):
C26H52NO7P
CAS Number:
19420-56-5
Molecular Weight:
521.67
Beilstein:
4033747
MDL number:
MFCD00133435
UNSPSC Code:
12352211
PubChem Substance ID:
24896294
NACRES:
NA.25

biological source

synthetic

Quality Level

200

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

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Application

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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Toxicology letters, 288, 65-70 (2018-02-20)
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