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P3644

Sigma-Aldrich

L-α-Phosphatidylcholine

from soybean, Type IV-S, ≥30% (enzymatic)

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:
51321705
NACRES:
NA.25
Pricing and availability is not currently available.

biological source

soybean

Quality Level

type

Type IV-S

form

solid

concentration

≥30% (enzymatic)

solubility

chloroform: soluble 100 mg/mL, clear to slightly hazy, yellow to orange

functional group

phospholipid

lipid type

phosphoglycerides

shipped in

ambient

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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Application

L-α-Phosphatidylcholine is suitable for use:
  • as a component of human erythroid massive amplification culture (HEMAdef) medium for clinical expansion of human erythroblasts[1]
  • in the chloride efflux assay to examine the chloride permeability of lipid vesicles conferred by soluble CLIC1[2]
  • in an assay to measure solubilized wax synthase activity[3]
  • as a component of buffer A used for the resuspension of the cholate-solubilized catalytic unit of adenylate cyclase[4]
  • as a cryoprotectant for freezing ruminant sperm[5]
  • as a substrate for the estimation of phospholipase activity[6]
  • to make liposomes to assess their efficiency of recruitment of ARF (ADP ribosylation factor) and AP-1 (adaptor protein)[7]
  • in the preparation of the isolated catalytic unit of soluble adenylate cyclase[8]

Biochem/physiol Actions

A major structural phospholipid in brain, comprising approx. 15% of total lipid; primarily localized to gray matter.
Phosphatidylcholine is the major membrane phospholipid in eukaryotic cells, forming the structural component of these membranes. It also serves as a reservoir for several lipid messengers and a source for several bioactive lipids such as, lysophosphatidylcholine, phosphatidic acid, diacylglycerol, lysophosphatidylcholine, platelet activating factor, and arachidonic acid.[9]

Preparation Note

Purified from P 5638

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

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J W Winslow et al.
The Journal of biological chemistry, 261(17), 7626-7634 (1986-06-15)
ATP analogues were used to study the active site specificity of the catalytic unit (C) of solubilized and partially purified bovine brain caudate nucleus adenylate cyclase. Phenylenediamine ATP (PD-ATP), 8-azido ATP (8-N3ATP), chromium(III) 3'-beta-alanylarylazido ATP (CrATPa), and 2',3'-dialdehyde ATP (oATP)
Carlos Andres Morales Letona et al.
Polymers, 11(2) (2019-04-10)
Here, we report a facile and effective one-pot approach to prepare uniform amylose-based polymeric microparticles (PMPs) through enzymatic synthesis of short-chain amylose (SCA) followed by spontaneous self-assembly of the SCA in the presence of lecithin. The effect of lecithin on
W Jiang et al.
Proceedings of the National Academy of Sciences of the United States of America, 98(9), 4966-4971 (2001-04-26)
The stoichiometry of c subunits in the H(+)-transporting F(o) rotary motor of ATP synthase is uncertain, the most recent suggestions varying from 10 to 14. The stoichiometry will determine the number of H(+) transported per ATP synthesized and will directly
Annie Frelet-Barrand et al.
PloS one, 5(1), e8746-e8746 (2010-01-26)
Despite their functional and biotechnological importance, the study of membrane proteins remains difficult due to their hydrophobicity and their low natural abundance in cells. Furthermore, into established heterologous systems, these proteins are frequently only produced at very low levels, toxic
Masayuki Iwamoto et al.
ACS synthetic biology, 7(4), 1004-1011 (2018-03-24)
Processes involved in the functional formation of prokaryotic membrane proteins have remained elusive. Here, we developed a new in vitro membrane protein expression system to detect nascent activities of the KcsA potassium channel in lipid bilayers under an applied membrane

Questions

1–4 of 4 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. It is said that it has also been used in cell culture, but is Chloroform or Ether harmless in cell culture? Also, is it completely insoluble in other organic solvents such as Chloroform, Ether, and DMSO?

    1 answer
    1. The product's solubility is tested in chloroform at a concentration of 100 mg/mL. Purified egg L-α-phosphatidylcholine is soluble (100 mg/mL) at room temperature in chloroform, ethanol, and hexane containing 3% ethanol. These solubility characteristics should generally apply to other purified natural product phosphatidylcholine products, such as those from soybean and brain, that contain unsaturated fatty acids. The product's solubility in dimethyl sulfoxide has not been determined. It is advised to check specific cells or cell lines to determine their sensitivity to solvents such as dimethyl sulfoxide, chloroform, and ether.

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  4. What kind of product is it, a powder?

    1 answer
    1. This product is listed as a solid but can range in appearance from waxy to powdery. The consistency is not a tested product specification and is simply reported as a solid. Please see the link below to review the product datasheet for additional information:
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/P3644-100G0000285416.pdf

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