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Phosphatidylethanolamines (egg) Sale

(Synonyms: 磷脂酰乙醇胺) 目录号 : GC44632

A glycerophospholipid

Phosphatidylethanolamines (egg) Chemical Structure

Cas No.:39382-08-6

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产品描述

Phosphatidylethanolamine is the most abundant phospholipid in prokaryotes and the second most abundant found in the membrane of mammalian, plant, and yeast cells, comprising approximately 25% of total mammalian phospholipids. In the brain, phosphatidylethanolamine comprises almost half of the total phospholipids. It is synthesized mainly through the cytidine diphosphate-ethanolamine and phosphatidylserine decarboxylation pathways, which occur in the endoplasmic reticulum (ER) and mitochondrial membranes, respectively. It is a precursor in the synthesis of phosphatidylcholine and arachidonoyl ethanolamide and is a source of ethanolamine used in various cellular functions. In E. coli, phosphatidylethanolamine deficiency prevents proper assembly of lactose permease, suggesting a role as a lipid chaperone. It is a cofactor in the propagation of prions in vitro and can convert recombinant mammalian proteins into infectious molecules even in the absence of RNA. Phosphatidylethanolamines (egg) is a mixture of phosphatidylethanolamines isolated from egg with various fatty acyl groups at the sn-1 and sn-2 positions.

Chemical Properties

Cas No. 39382-08-6 SDF
别名 磷脂酰乙醇胺
Canonical SMILES [R]C(OC[C@H](OC([R])=O)COP([O-])(OCC[NH3+])=O)=O
分子式 C41H78NO8P (for oleoyl) 分子量 744
溶解度 Chloroform: soluble 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 1.3441 mL 6.7204 mL 13.4409 mL
5 mM 0.2688 mL 1.3441 mL 2.6882 mL
10 mM 0.1344 mL 0.672 mL 1.3441 mL
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Research Update

egg yolk phospholipids as an ideal precursor of fatty note odorants for chicken meat and fried foods: A review

Food Chem 2023 May 1;407:135177.PMID:36527950DOI:10.1016/j.foodchem.2022.135177.

egg yolk phospholipids (PLs) have been demonstrated to generate large quantities of lipid-derived odorants, especially the fatty note odorants. Recently, egg yolk PLs have been successfully used in chicken meat and fried foods to improve aroma. This review comprehensively summarizes the properties of egg yolk PLs as precursors of fatty note odorants, including their classes, extraction, identification, oxidation, decomposition and odorant formation, applications, considerations and future prospects in the food industry. Most likely, phosphatidylcholine (PC) is the most abundant class in egg yolk PLs, and PC is more efficient than phosphatidylethanolamine in generating fatty note odorants; moreover, the predominant polyunsaturated fatty acid is linoleic acid, and its corresponding predominant hydroperoxide is 9-hydroperoxy-10,12-octadecadienoic acid during autoxidation, which is the precursor of 2,4-decadienals and 2,4-nonadienals, the key fatty note odorants. Therefore, egg yolk PLs could be an ideal precursor of fatty note odorants for chicken meat and fried foods.

egg Yolk Phosphatidylethanolamine: Extraction Optimization, Antioxidative Activity, and Molecular Structure Profiling

J Food Sci 2019 May;84(5):1002-1011.PMID:30977912DOI:10.1111/1750-3841.14512.

Although phosphatidylethanolamine (PE) is an important functional phospholipid, there have been very few reports on its antioxidant activity and corresponding molecular composition. Crude PE was extracted from egg yolk with various solvents, and response surface modeling was carried out to determine the optimum extraction conditions for PE, under which the PE content in extracts reached 58.94 µg/mL. The crude PE was purified using silica gel-based column chromatography. High-purity PE (98%), identified by high-performance liquid chromatography-evaporative light-scattering detector, was obtained using isocratic elution with a mixed solvent (chloroform: methanol: acetic acid = 18:5:1) eluent. PE purified from egg yolk exhibited high radical-scavenging activity, determined by electron paramagnetic resonance (EPR). The result was attributed to the high unsaturated fatty acids (83.10%) content in egg yolk PE, and the unsaturated fatty acids were identified as PE-16:0/18:1Δ 9 , PE-16:0/18:2Δ 9,12 , PE-16:0/20:4Δ 5,8,11,14 , PE-18:0/18:1Δ 9 , PE-18:0/18:2Δ 9,12 , and PE-18:0/20:4Δ 5,8,11,14 by MALDI-TOF MS combined with gas chromatography mass spectrometry. PRACTICAL APPLICATION: In this work, an attempt has been made to explore the antioxidant activity of PE that extracted and purified from egg yolk and its corresponding molecular composition. Owing to its plentiful unsaturated fatty acids (83.10%), purified PE from egg yolk exhibited a high radical-scavenging activity that indicated that egg-yolk PE had a strong antioxidant activity, and it might exert possible beneficial effects on the human health.

Lipidomics of the chicken egg yolk: high-resolution mass spectrometric characterization of nutritional lipid families

Poult Sci 2021 Feb;100(2):887-899.PMID:33518142DOI:10.1016/j.psj.2020.11.020.

While previous studies have characterized the fatty acids and global lipid families of the chicken egg yolk, there have been no publications characterizing the individual lipids in these lipid families. Such an in-depth characterization of egg yolk lipids is essential to define the potential benefits of egg yolk consumption for the supply of structural and anti-inflammatory lipids. Historically, the major focus has been on the cholesterol content of eggs and the potential negative health benefits of this lipid, while ignoring the essential roles of cholesterol in membranes and as a precursor to other essential sterols. A detailed analysis of egg yolk lipids, using high-resolution mass spectrometric analyses and tandem mass spectrometry to characterize the fatty acid substituents of complex structural lipids, was used to generate the first in-depth characterization of individual lipids within lipid families. egg yolks were isolated from commercial eggs (Full Circle Market) and lipids extracted with methyl-t-butylether before analyses via high-resolution mass spectrometry. This analytical platform demonstrates that chicken egg yolks provide a rich nutritional source of complex structural lipids required for lipid homeostasis. These include dominant glycerophosphocholines (GPC) (34:2 and 36:2), plasmalogen GPC (34:1, 36:1), glycerophosphoethanolamines (GPE) 38:4 and 36:2), plasmalogen GPE (36:2 and 34:1), glycerophosphoserines (36:2 and 38:4), glycerophosphoinositols (38:4), glycerophosphoglycerols (36:2), N-acylphosphatidylethanolamines (NAPE) (56:6), plasmalogen NAPE (54:4 and 56:6), sphingomyelins (16:0), ceramides (22:0 and 24:0), cyclic phosphatidic acids (16:0 and 18:0), monoacylglycerols (18:1 and 18:2), diacylglycerols (36:3 and 36:2), and triacylglycerols (52:3). Our data indicate that the egg yolk is a rich source of structural and energy-rich lipids. In addition, the structural lipids possess ω-3 and ω-6 fatty acids that are essential precursors of endogenous anti-inflammatory lipid mediators. These data indicate that eggs are a valuable nutritional addition to the diets of individuals that do not have cholesterol issues.

Quantitative lipidomic analysis of chicken egg yolk during its formation

J Sci Food Agric 2023 Jun;103(8):3997-4005.PMID:36426805DOI:10.1002/jsfa.12354.

Background: The accumulation of lipids in egg yolk during its formation represents a knowledge gap between food science and animal science research to which researchers in either field have not paid sufficient attention. Therefore, the egg yolk samples during different periods of formation (yellow follicle, YF; small hierarchical follicles, SF; and the largest hierarchical follicle, LF) were prepared, and their fatty acid compositions and lipidomes were quantitatively compared. Results: The fatty acid profiles and lipidomes of egg yolks at the three stages of formation were significantly different. The relative content of oleic acid and palmitic acid were increased, but that of the main polyunsaturated fatty acids (linoleic acid, linolenic acid and docosahexaenoic acid) was decreased in the SF period to the LF period. Among the 786 lipid molecular species identified, 150 and 46 differentially abundant lipids (DALs) were identified in the pairwise comparison of YF/SF (early stage of egg yolk formation) and SF/LF (late stage of egg yolk formation), respectively. Triglycerides and diglycerides, represented by TG(14:0/18:1/20:1) and DG(18:1/18:1/0:0), were decreased, whereas free fatty acids (especially free unsaturated fatty acids) were greatly increased during yolk formation. The changes in phospholipids were complex; the relative abundance of phosphatidylcholine [represented by PC(18:0/22:5)] decreased, whereas phosphatidylethanolamine [represented by PE(18:0/18:0)] increased. In addition, the relative abundance of lysophosphatidylcholine [represented by LPC(18:1/0:0)] was increased during egg yolk formation. Conclusion: The transport and accumulation of lipids into the egg yolk is dynamically adjusted during its formation, and the transport and timing of different lipid molecular species are different. © 2022 Society of Chemical Industry.

Liposomes as an alternative to egg yolk in stallion freezing extender

Theriogenology 2012 Jan 15;77(2):268-79.PMID:21924469DOI:10.1016/j.theriogenology.2011.08.001.

egg yolk is normally used as a protective agent to freeze semen of equine and other species. However, addition of egg yolk in extenders is not without disadvantages and the demand to find cryoprotective alternatives is strong. The objective of this study was to test the cryoprotective capacities of liposomes composed of egg yolk phospholipids. Two experiments were conducted: 1) the first to determine the optimal composition and concentration of liposomes to preserve post-thaw motility and membrane integrity of spermatozoa; 2) the second to assess in vivo the cryoprotective capacities of these liposomes. In Experiment 2, post-thaw motility and membrane integrity of spermatozoa were also analyzed. Experiment 1 demonstrated that liposomes composed of phospholipids E80 (commercial lecithins from egg yolk composed mainly of phosphatidylcholine and phosphatidylethanolamine) and of Hank's salts-glucose-lactose solution (E80-liposomes) were the most efficient in preserving post-thaw motility. The optimal concentration was 4 % (v/v). In Experiment 2, fertility rate after artificial insemination of semen frozen with E80-liposomes was 55 % (22/40) compared with 68 % (27/40) with the control extender containing egg yolk (EY) (p = 0.23). Post-thaw motility parameters were higher with EY than with E80-liposomes (p < 0.0001). For post-thaw membrane integrity no difference was observed between the two extenders (p = 0.08). Liposomes composed of egg yolk phospholipids appeared to be a promising alternative to replace egg yolk in semen freezing extenders in equine species.