All Photos(4)

P3556

Sigma-Aldrich

L-α-Phosphatidylcholine

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

Synonym(s):
L-α-Lecithin, Azolectin, 3-sn-Phosphatidylcholine, PC, 1,2-Diacyl-sn-glycero-3-phosphocholine
CAS Number:
Beilstein:
5209585
EC Number:

biological source

egg yolk

Quality Level

type

Type XVI-E

assay

≥99% (TLC)

form

lyophilized powder

functional group

phospholipid

shipped in

ambient

storage temp.

−20°C

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

InChI key

JLPULHDHAOZNQI-ZTIMHPMXSA-N

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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.

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

Packaging

25, 100, 500 mg in glass bottle
1 g in glass bottle
Packaged under Argon

Biochem/physiol Actions

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

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 Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
FTIR-spectroscopic characterization of phosphocholine-headgroup model compounds
Pohle W, et al.
Journal of Molecular Structure, 563, 463-467 (2001)
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)
Lea M Hürlimann et al.
Antimicrobial agents and chemotherapy, 60(9), 5400-5411 (2016-07-07)
Nosocomial infections with Enterococcus faecalis are an emerging health problem. However, drug efflux pumps contributing to intrinsic drug resistance are poorly studied in this Gram-positive pathogen. In this study, we functionally investigated seven heterodimeric ABC transporters of E. faecalis that...
Marine omega-3 phospholipids: metabolism and biological activities
Burri L, et al.
International Journal of Molecular Sciences, 13(11), 15401-15419 (2012)

Protocols

LC/MS Analysis of Phospholipids in Milk on Ascentis® Express HILIC after SPE using Supelclean Si, Shotgun HPLC Analysis

(soybean), ≥97%; L-α-Phosphatidylethanolamine from egg yolk, Type III, ≥97% (TLC), lyophilized powder; L-α-Phosphatidylcholine, from egg yolk, Type XVI-E, ≥99% (TLC), lyophilized powder; Sphingomyelin, from chicken egg yolk, ≥95%

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