P5638

L-α-Phosphatidylcholine

from soybean, Type II-S, 14-29% choline basis

• Synonym(s): 1,2-Diacyl-sn-glycero-3-phosphocholine, 3-sn-Phosphatidylcholine, L-α-Lecithin, Azolectin, PC
• CAS Number: 8002-43-5
• UNSPSC Code: 12352211
• NACRES: NA.25
• EC Number: 232-307-2
• Beilstein/REAXYS Number: 5209585

Properties

• biological source: soybean
• Quality Segment: 200
• type: Type II-S
• form: powder or solid
• concentration: 14-29% (choline)
• functional group: phospholipid
• lipid type: phosphoglycerides
• shipped in: ambient
• storage temp.: 2-8°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

Description

General description

P5638 is a crude extract of soybean phospholipids.

Typical lots of purified soybean phosphatidylcholine have fatty acid contents of approximately 13% C16:0 (palmitic), 4% C18:0 (stearic), 10% C18:1(oleic), 64% C18:2 (linoleic), and 6% 18:3 (linolenic) with other fatty acids being minor contributors. This would calculate to an average molecular weight of approximately 776.

Purified phosphatidylcholine is soluble in chloroform and ethanol.

Other major phospholipid components include phosphatidylethanolamine and inositol phosphatides. Other phospholipids and neutral lipids such as triglycerides, tocopherols, and sterols may be present. Carbohydrates may also be present.

A procedure for determination of the amount of oxidation of egg phosphatidylcholine in a liposome preparation by measurement of the oxidation index has been published. The oxidation index is the ratio of the absorbance at 233 nm to the absorbance at 215 nm. The latter wavelength was chosen since there is little contribution of the fatty acid carbonyl to the absorbance at this wavelength, allowing Beer′s Law to be followed.

A method of determining choline content has been published.

Application

L-α-Phosphatidylcholine has been used:

• as a component in the test freezing medium (TFM) formulated for cryopreservation of prepubertal testicular tissue
• to investigate its effects on the fluorescence signals in voltage-clamp fluorometry (VCF)
• to prepare soy lecithin liposomes for the biotransformation into lysolecithin and fatty acids for valorization of soy lecithin by enzyme cascade reactions

Biochem/physiol Actions

Phosphatidylcholine is the major membrane phospholipid in eukaryotic cells. In addition to being the major structural component of cellular membranes, phosphatidylcholine serves as a reservoir for several lipid messengers. It is the source of the bioactive lipids lysophosphatidylcholine, phosphatidic acid, diacylglycerol, lysophosphatidylcholine, platelet activating factor, and arachidonic acid.

Phosphatidylcholine is used for preparation of vesicle suspensions, commonly called liposomes, or as monolayers. Monolayers have been formed using a solution of 1% soybean phosphatidylcholine in hexane.

Valinomycin-induced changes in membrane potentials of red blood cell and phospholipid (phosphatidylcholine from egg yolk plus cholesterol) vesicle suspensions have been measured using positively-charged, cyanine dyes that fluorimetrically responded to the change in potential.

Purified rhodopsin has been incorporated into soybean phosphatidylcholine vesicles.

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

Analysis Note

P5638 is a crude soy extract that contains many other lipids.

Safety Information

• Storage Class: 11 - Combustible Solids
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): Eyeshields, Gloves, type N95 (US)