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Merck

P3556

L-α-Phosphatidylcholine

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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About This Item

CAS Number:
8002-43-5
UNSPSC Code:
51321705
NACRES:
NA.25
EC Number:
232-307-2
Beilstein/REAXYS Number:
5209585

Key Documents

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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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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

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.

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)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

P3556-BULK-N: + P3556-25MG-PW: + P3556-VAR: + P3556PROC: + P3556-1G-PW: + P3556-100MG-KC: + P3556-PH: + P3556-100MG-PW: + P3556-250MG: + P3556-500MG-PW: + P3556-BULK: + P3556-1G: + P3556-25MG: + P3556-500MG: + P3556-100MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000519309
0000519309
0000478236
0000478236
0000469230

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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
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)
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)
Marine omega-3 phospholipids: metabolism and biological activities
Burri L, et al.
International Journal of Molecular Sciences, 13(11), 15401-15419 (2012)
View All Related Papers

Protocols

LC/MS Analysis of Phospholipids in Milk on Asc

(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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Product Information Sheet - P3556

Product Information Sheet

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