P3556

L-α-Phosphatidylcholine

Name: <SC>L</SC>-α-Phosphatidylcholine
Brand: SIGMA

egg yolk, Type XVI-E, ≥99% (TLC), lyophilized powder

Synonym(s):

1,2-Diacyl-sn-glycero-3-phosphocholine, 3-sn-Phosphatidylcholine, L-α-Lecithin, Azolectin, PC

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All Photos(4)

About This Item

CAS Number:

8002-43-5

UNSPSC Code:

51321705

NACRES:

NA.25

EC Number:

232-307-2

Beilstein/REAXYS Number:

5209585

Product Name

L-α-Phosphatidylcholine, egg yolk, Type XVI-E, ≥99% (TLC), lyophilized powder

SMILES string

[P](=O)([O-])(OC[C@H](OC(=O)CCCCCCC\C=C/C\C=C/CCCCC)COC(=O)CCCCCCCCCCCCCCC)OCC[N+](C)(C)C

InChI key

JLPULHDHAOZNQI-ZTIMHPMXSA-N

InChI

1S/C42H80NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1

biological source

egg yolk

type

Type XVI-E

assay

≥99% (TLC)

form

lyophilized powder

functional group

phospholipid

lipid type

phosphoglycerides

shipped in

ambient

storage temp.

−20°C

Quality Level

200

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Related Categories

Biochemicals

Lipids and Lipid Derivatives for Research

Application

L-α-Phosphatidylcholine has been used:

to form a thin lipid film used in Kupffer cell depletion by liposome-encapsulated clodronate
as a component of assay buffer used in γ-secretase in vitro assay
in the preparation of substrate mix for its use in HPLC (high performance liquid chromatography) assay of 5-lipoxygenase enzyme activity

Biochem/physiol Actions

A major structural phospholipid in brain, comprising approx. 15% of total lipid; primarily localized to gray matter.

It also acts as a source of lipid messengers/ bioactive lipids including: lysophosphatidylcholine, diacylglycerol, phosphatidic acid, lysophosphatidylcholine, arachidonic acid and platelet activating factor. Phosphatidylcholine is produced in the liver by the CDP-choline (cytidine diphosphocholine) pathway.

General description

Phosphatidylcholine belongs to the class of glycerophoshpolipids and contains choline as the head-group. Choline is attached to the glycerol of fatty acids ester-bound to backbone. It is the major phospholipid found in eukaryotic organism.

Packaging

Packaged under Argon

Preparation Note

Prepared by a modification of the procedure of Singleton, W.S., et al., J. Am. Oil Chem. Soc., 42, 53 (1965).

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000519309

0000478236

0000469230

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Marine omega-3 phospholipids: metabolism and biological activities

Burri L, et al.

International Journal of Molecular Sciences, 13(11), 15401-15419 (2012)

Molecular distinction of phosphatidylcholine synthesis between the CDP-choline pathway and phosphatidylethanolamine methylation pathway

DeLong CJ, et al.

The Journal of Biological Chemistry, 274(42), 29683-29688 (1999)

Coactosin-like protein supports 5-lipoxygenase enzyme activity and up-regulates leukotriene A4 production

Rakonjac M, et al.

Proceedings of the National Academy of Sciences of the USA, 103(35), 13150-13155 (2006)

FTIR-spectroscopic characterization of phosphocholine-headgroup model compounds

Pohle W, et al.

Journal of Molecular Structure, 563, 463-467 (2001)

Chemical cross-linking provides a model of the gamma-secretase complex subunit architecture and evidence for close proximity of the C-terminal fragment of presenilin with APH-1

Steiner H, et al.

The Journal of Biological Chemistry, 283(50), 34677-34686 (2008)

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