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Key Documents

P5638

Sigma-Aldrich

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

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About This Item

CAS Number:
Beilstein:
5209585
EC Number:
UNSPSC Code:
12352211
NACRES:
NA.25

biological source

soybean

Quality Level

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

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

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.

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.

Quality

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D M Mihai et al.
Cell death & disease, 5, e1348-e1348 (2014-07-25)
Cellular events responsible for the initiation of major neurodegenerative disorders of the eye leading to blindness, including age-related macular degeneration, Stargardt and Best diseases, are poorly understood. Accumulation of vitamin A dimers, such as N-retinylidene-N-retinylethanolamine (A2E) in the retinal pigment
The detection of oxidation in liposome preparations.
R A Klein
Biochimica et biophysica acta, 210(3), 486-489 (1970-09-08)
R Cassia-Moura et al.
Journal of theoretical biology, 206(2), 235-241 (2000-09-01)
Dynamic activation of ion channels formed by colicin Ia incorporated into a planar bilayer lipid membrane (BLM) was investigated by the voltage clamp technique using different step voltage stimuli. We have demonstrated a critical resting interval, Deltat(c), between two identical
Cedric Orelle et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(35), 12837-12842 (2008-08-30)
The maltose transporter MalFGK(2) of Escherichia coli is a member of the ATP-binding cassette superfamily. A periplasmic maltose-binding protein (MBP) delivers maltose to MalFGK(2) and stimulates its ATPase activity. Site-directed spin labeling EPR spectroscopy was used to study the opening
Liposomes in Gene Delivery
Lasic, D.D. et al.
CRC Press (1997)

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