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P7943

Sigma-Aldrich

L-α-Phosphatidylethanolamine from egg yolk

Type III, ≥97% (TLC), lyophilized powder

Synonym(s):

1,2-Diacyl-sn-glycero-3-phosphoethanolamine, L-α-Cephalin

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About This Item

CAS Number:
EC Number:
MDL number:
UNSPSC Code:
51191904
NACRES:
NA.25
Pricing and availability is not currently available.

biological source

egg yolk

Quality Level

type

Type III

Assay

≥97% (TLC)

form

lyophilized powder

functional group

phospholipid

lipid type

phosphoglycerides

shipped in

ambient

storage temp.

−20°C

SMILES string

[P](=O)(OC[C@H](OC(=O)CCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCC)(OCCN)O

InChI

1S/C40H80NO8P/c1-3-5-7-9-11-13-15-17-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41)36-46-39(42)32-30-28-26-24-22-16-14-12-10-8-6-4-2/h38H,3-37,41H2,1-2H3,(H,44,45)/t38-/m1/s1

InChI key

NJGIRBISCGPRPF-KXQOOQHDSA-N

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General description

L-α-Phosphatidylethanolamine from egg yolk has high unsaturated fatty acid content and elicits radical-scavenging activity.[1] L-α-Phosphatidylethanolamine (PE) is a membrane phospholipid and is interconverted to phosphotidylserine in the presence of phosphatidylserine synthase 2. PE is essential for maintaining the structural integrity of membranes.[2] It is the second most abundant phospholipid in animals, plants and yeast and the major lipid in bacteria. It is synthesized in mitochondria in mammals.[3]

Application

L-α-Phosphatidylethanolamine from egg yolk has been used:
  • as a component of lipid mixture for the synthesis of giant unilamellar vesicles (GUVs)[4]
  • in ceramide phosphoethanolamine (CPE) synthase assay using crude sphingomyelin synthase-related protein from Hela cells[5]
  • for the standard curve generation for the quantification of lipids in plantaris muscle homogenates from mice[6]

Packaging

Packaged under Argon.

Caution

Purity when prepared is 97-99%. Solutions exposed to room temperature can decompose 0.3-0.5% per day.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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Scolopendin 2, a cationic antimicrobial peptide from centipede, and its membrane-active mechanism
Lee H, et al.
Biochimica et Biophysica Acta - Biomembranes, 1848(2), 634-642 (2015)
Egg Yolk Phosphatidylethanolamine: Extraction Optimization, Antioxidative Activity, and Molecular Structure Profiling
Sun N, et al.
Journal of Food Science (2019)
Elevated whole muscle phosphatidylcholine: phosphatidylethanolamine ratio coincides with reduced SERCA activity in murine overloaded plantaris muscles
Fajardo VA, et al.
Lipids in Health and Disease, 17(1), 47-47 (2018)
Tingbo Ding et al.
Journal of lipid research, 56(3), 537-545 (2015-01-22)
Sphingomyelin synthase-related protein (SMSr) synthesizes the sphingomyelin analog ceramide phosphoethanolamine (CPE) in cells. Previous cell studies indicated that SMSr is involved in ceramide homeostasis and is crucial for cell function. To further examine SMSr function in vivo, we generated Smsr
All members in the sphingomyelin synthase gene family have ceramide phosphoethanolamine synthase activity
Ding T, et al.
Journal of Lipid Research, 56(3), 537-545 (2015)

Protocols

(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%

(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%

(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%

(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%

Questions

1–3 of 3 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. What solvents are used to dissolve phosphatidylethanolamine?  What is the solubility?  What solvent is.least toxic to eucaryotic cells?

    1 answer
    1. This solubility is tested in CHCl3 at 25 mg/mL. Stock solutions in chloroform can be added to medium or buffer and allowed to stir prior to filtration. This allows the chloroform to evaporate off while keeping the Phosphatidylethanolamine in solution, thereby avoiding the risk of exposing cells to the solvent. An alternative solvent would be a mixture of chloroform and methanol, which would also be cytotoxic. Please see the sample Certificate of Analysis:
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/P7943-BULKSLCN2430.pdf

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