P4279

L-α-Phosphatidylcholine

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

egg yolk, Type XIII-E, 100 mg/mL in ethanol, solution

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

Beilstein/REAXYS Number:

5209585

UNSPSC Code:

51321705

NACRES:

NA.25

Key Documents

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biological source

egg yolk

type

Type XIII-E

assay

≥99% (TLC)

form

solution

concentration

100 mg/mL in ethanol

functional group

phospholipid

lipid type

phosphoglycerides

storage temp.

−20°C

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

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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Show Differences

1 of 4

This Item	P3556	P3782	P2772
Sigma-Aldrich P4279 L-α-Phosphatidylcholine	Sigma-Aldrich P3556 L-α-Phosphatidylcholine	Sigma-Aldrich P3782 L-α-Phosphatidylcholine	Sigma-Aldrich P2772 L-α-Phosphatidylcholine
biological source egg yolk	biological source egg yolk	biological source soybean	biological source egg yolk
functional group phospholipid	functional group phospholipid	functional group -	functional group phospholipid
assay ≥99% (TLC)	assay ≥99% (TLC)	assay ≥98%	assay ≥99%
form solution	form lyophilized powder	form solution	form solution
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
concentration 100 mg/mL in ethanol	concentration -	concentration 100 mg/mL in chloroform	concentration 100 mg/mL in chloroform

General description

Phosphatidylcholine is the major membrane phospholipid in eukaryotic cells.[1] This structural component of the cellular membrane is the source of the bioactive lipids lysophosphatidylcholine, phosphatidic acid, diacylglycerol, lysophosphatidylcholine, platelet-activating factor, and arachidonic acid.

Application

L-α-Phosphatidylcholine has been used in differential lipid partitioning experiments of xenobiotics and natural compounds to determine trioleoylglycerol (TG) and phosphatidylcholine (PC) coefficients (KTG/PC) for partitioning of lipophilic chemicals.[2]

Biochem/physiol Actions

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

Phosphatidylcholine serves as a reservoir for several lipid messengers.[1] Phosphatidylcholine is used for the preparation of vesicle suspensions, commonly called liposomes or monolayers.[3]

pictograms

GHS02,GHS07

signalword

Danger

hcodes

H225,H319

pcodes

P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

60.8 °F

flash_point_c

16 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number

0000492123

0000498736

0000487348

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Membrane lipids: where they are and how they behave.

Gerrit van Meer et al.

Nature reviews. Molecular cell biology, 9(2), 112-124 (2008-01-25)

Throughout the biological world, a 30 A hydrophobic film typically delimits the environments that serve as the margin between life and death for individual cells. Biochemical and biophysical findings have provided a detailed model of the composition and structure of

Biosynthesis of phosphatidylcholine by human lysophosphatidylcholine acyltransferase 1.

Takeshi Harayama et al.

Journal of lipid research, 50(9), 1824-1831 (2009-04-23)

Pulmonary surfactant is a complex of phospholipids and proteins lining the alveolar walls of the lung. It reduces surface tension in the alveoli, and is critical for normal respiration. Pulmonary surfactant phospholipids consist mainly of phosphatidylcholine (PC) and phosphatidylglycerol (PG).

A review on phospholipids and their main applications in drug delivery systems

Li J, et al.

Asian Journal of Pharmaceutical Sciences , 10, 81-98 (2015)

Selection of Thai Medicinal Plants with Anti-Obesogenic Potential via In Vitro Methods.

Wijitrapha Ruangaram et al.

Pharmaceuticals (Basel, Switzerland), 13(4) (2020-04-03)

The prevalence of obesity is increasing globally. Despite the availability of a variety of anti-obesogenic drugs, including therapies under clinical development, these treatments are often indicated for patients with severe obesity, making them unsuitable for patients with mild obesity or

Differential lipid affinity of xenobiotics and natural compounds.

Heinrich Sandermann

FEBS letters, 554(1-2), 165-168 (2003-11-05)

Octanol-1/water partitioning currently provides the most widely used model system to simulate both phospholipid target lipids and triglyceride storage lipids. A differentiation between the two lipid classes is now achieved by making use of a water-induced lipid phase separation. Coefficients

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