Phosphatidyl choline (from egg yolk) | CAS#8002-43-5 | CAS#8057-53-2

MedKoo Cat#: 510262B | Name: Phosphatidyl choline (from egg yolk)

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. They are a major component of biological membranes and can be easily obtained from a variety of readily available sources, such as egg yolk or soybeans, from which they are mechanically or chemically extracted using hexane. They are also a member of the lecithin group of yellow-brownish fatty substances occurring in animal and plant tissues. Dipalmitoyl phosphatidylcholine (aka: lecithin) is a major component of pulmonary surfactant and is often used in the L/S ratio to calculate fetal lung maturity. While phosphatidylcholines are found in all plant and animal cells, they are absent in the membranes of most bacteria, including Escherichia coli. Purified phosphatidylcholine is produced commercially.

Chemical Structure

Phosphatidyl choline (from egg yolk)

CAS#8057-53-2 (from egg yolk)

Theoretical Analysis

MedKoo Cat#: 510262B

Name: Phosphatidyl choline (from egg yolk)

CAS#: 8057-53-2 (from egg yolk)

Chemical Formula: N/A (mixture)

Exact Mass: 0.0000

Molecular Weight: 0.00

Elemental Analysis: N/A (mixture)

Price and Availability

Size	Price	Availability
500g	USD 3,150.00	2-3 months
1kg	USD 4,750.00	2-3 months
2kg	USD 6,950.00	2-3 months

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Related CAS #

8057-53-2 (from egg yolk) 8002-43-5 (from Soybean)

Synonym

1,2-Diacyl-sn-glycero-3-phosphocholine, 3-sn-Phosphatidylcholine, L-α-Lecithin, Azolectin, PC. Phosphatidyl choline.

IUPAC/Chemical Name

(Z)-3-(oleoyloxy)-2-(palmitoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate.

InChi Key

RRVPPYNAZJRZFR-MRCUWXFGSA-N

InChi Code

InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-25-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-

SMILES Code

O=P(OCC(OC(CCCCCCCCCCCCCCC)=O)COC(CCCCCCC/C=C\CCCCCCCC)=O)([O-])OCC[N+](C)(C)C

Appearance

Yellow to light brown semi-solid or wax solid.

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2923202000

More Info

Phosphatidylcholine is a major constituent of cell membranes and pulmonary surfactant, and is more commonly found in the exoplasmic or outer leaflet of a cell membrane. It is thought to be transported between membranes within the cell by phosphatidylcholine transfer protein (PCTP). Phosphatidylcholine also plays a role in membrane-mediated cell signaling and PCTP activation of other enzymes. The phospholipid is composed of a choline head group and glycerophosphoric acid, with a variety of fatty acids, one being a saturated fatty acid (in the given figure, this can be palmitic or hexadecanoic acid, H3C-(CH2)14-COOH; margaric acid identified by Gobley in egg yolk, or heptadecanoic acid H3C-(CH2)15-COOH, also belong to that class); and one being an unsaturated fatty acid (here oleic acid, or 9Z-octadecenoic acid, as in Gobley's original egg yolk lecithin). Phospholipase D catalyzes the hydrolysis of phosphatidylcholine to form phosphatidic acid (PA), releasing the soluble choline headgroup into the cytosol. Phosphatidylcholine is a neutral lipid, but it carries an electric dipole moment of about 10 D. (http://en.wikipedia.org/wiki/Phosphatidylcholine)

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup.

In vitro activity:

Results showed that 95D cells proliferation and adherence in the DHA-PC (docosahexaenoic acid-containing phosphatidylcholine) or EPA-PC (eicosapentaenoic acid-containing phosphatidylcholine) group were drastically inhibited than the control group. DHA-PC and EPA-PC suppressed the migration and invasion of 95D cells by disrupting intracellular F-actin, which drives cell movement. The protein expression of PPARγ was induced versus the control group. Furthermore, critical factors related to invasion, including matrix metallopeptidase 9 (MMP9), heparanase (Hpa), and vascular endothelial growth factor (VEGF), were drastically downregulated through the PPARγ/NF-κB signaling pathway. Reference: Nutrients. 2022 Nov 4;14(21):4675. https://pubmed.ncbi.nlm.nih.gov/36364935/

In vivo activity:

Rats fed the PCHF (phosphatidylcholine high fat) diet had a lower proportion of CD3+ cells when compared to both the CLF and the CHF. Following PMA+I stimulation, splenocytes from the CHF group produced less IL-2 and TNF-α compared to CLF and PCHF groups. No significant differences in cytokine production were found among groups after LPS and PWM stimulation. These results show that feeding a high-fat diet impairs T-cell responses, as measured by ex vivo cytokine production, which can be attenuated by providing egg-PC. Reference: Front Nutr. 2022 Feb 2;9:811469. https://pubmed.ncbi.nlm.nih.gov/35187037/

Preparing Stock Solutions

The following data is based on the product molecular weight 0.00 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Yin H, Liu Y, Yue H, Tian Y, Dong P, Xue C, Zhao YT, Zhao Z, Wang J. DHA- and EPA-Enriched Phosphatidylcholine Suppress Human Lung Carcinoma 95D Cells Metastasis via Activating the Peroxisome Proliferator-Activated Receptor γ. Nutrients. 2022 Nov 4;14(21):4675. doi: 10.3390/nu14214675. PMID: 36364935; PMCID: PMC9654432. 2. Choi J, Song I, Lee S, You M, Kwon J. Protective Effects of Phosphatidylcholine against Hepatic and Renal Cell Injury from Advanced Glycation End Products. Medicina (Kaunas). 2022 Oct 25;58(11):1519. doi: 10.3390/medicina58111519. PMID: 36363476; PMCID: PMC9692888. 3. Azarcoya-Barrera J, Wollin B, Veida-Silva H, Makarowski A, Goruk S, Field CJ, Jacobs RL, Richard C. Egg-Phosphatidylcholine Attenuates T-Cell Dysfunction in High-Fat Diet Fed Male Wistar Rats. Front Nutr. 2022 Feb 2;9:811469. doi: 10.3389/fnut.2022.811469. PMID: 35187037; PMCID: PMC8847771. 4. Liu Y, Tian Y, Guo Y, Yan Z, Xue C, Wang J. DHA-enriched phosphatidylcholine suppressed angiogenesis by activating PPARγ and modulating the VEGFR2/Ras/ERK pathway in human umbilical vein endothelial cells. Food Sci Biotechnol. 2021 Oct 27;30(12):1543-1553. doi: 10.1007/s10068-021-00990-0. PMID: 34868703; PMCID: PMC8595343.

In vitro protocol:

In vivo protocol:

1. Azarcoya-Barrera J, Wollin B, Veida-Silva H, Makarowski A, Goruk S, Field CJ, Jacobs RL, Richard C. Egg-Phosphatidylcholine Attenuates T-Cell Dysfunction in High-Fat Diet Fed Male Wistar Rats. Front Nutr. 2022 Feb 2;9:811469. doi: 10.3389/fnut.2022.811469. PMID: 35187037; PMCID: PMC8847771. 2. Liu Y, Tian Y, Guo Y, Yan Z, Xue C, Wang J. DHA-enriched phosphatidylcholine suppressed angiogenesis by activating PPARγ and modulating the VEGFR2/Ras/ERK pathway in human umbilical vein endothelial cells. Food Sci Biotechnol. 2021 Oct 27;30(12):1543-1553. doi: 10.1007/s10068-021-00990-0. PMID: 34868703; PMCID: PMC8595343.

1: Miñones J, Muñoz M, Miñones Trillo J, Haro I, Busquets MA, Alsina Esteller MA. Miscibility and Langmuir studies of the interaction of E2 (279-298) peptide sequence of Hepatitis G Virus/GB Virus-C with Dipalmitoyl Phosphatidyl Choline and Dimiristoyl Phosphatidyl Choline phospholipids. Langmuir. 2015 Jul 10. [Epub ahead of print] PubMed PMID: 26161460. 2: Saini RK, Dube A, Gupta PK, Das K. Diffusion of chlorin-p6 across phosphatidyl choline liposome bilayer probed by second harmonic generation. J Phys Chem B. 2012 Apr 12;116(14):4199-205. doi: 10.1021/jp205335z. Epub 2012 Mar 29. PubMed PMID: 22414064. 3: Toimil P, Prieto G, Miñones J Jr, Trillo JM, Sarmiento F. Monolayer and Brewster angle microscopy study of human serum albumin-dipalmitoyl phosphatidyl choline mixtures at the air-water interface. Colloids Surf B Biointerfaces. 2012 Apr 1;92:64-73. doi: 10.1016/j.colsurfb.2011.11.022. Epub 2011 Nov 20. PubMed PMID: 22154096. 4: Gupta NK, Dixit VK. Bioavailability enhancement of curcumin by complexation with phosphatidyl choline. J Pharm Sci. 2011 May;100(5):1987-95. doi: 10.1002/jps.22393. Epub 2010 Nov 24. PubMed PMID: 21374628. 5: Miñones Conde M, Conde O, Trillo JM, Miñones J Jr. Approach to knowledge of the interaction between the constituents of contact lenses and ocular tears: mixed monolayers of poly(methyl methacrylate) and dipalmitoyl phosphatidyl choline. Langmuir. 2011 Apr 5;27(7):3424-35. doi: 10.1021/la1051172. Epub 2011 Mar 3. PubMed PMID: 21370907. 6: Gupta NK, Dixit VK. Absorption enhancement of grape seed polyphenols by complexation with phosphatidyl choline. Drug Deliv. 2011 Jul;18(5):312-9. doi: 10.3109/10717544.2010.544691. Epub 2011 Jan 22. PubMed PMID: 21254941. 7: Evans M, Sharma P, Guthrie N. A randomized, double-blind, crossover study on the pharmacokinetics of a novel formulation of CoQ₁₀ with pyridoxal 5'-phosphate and phosphatidyl choline. J Diet Suppl. 2010 Dec;7(4):314-24. doi: 10.3109/19390211.2010.522551. Epub 2010 Oct 11. PubMed PMID: 22432561. 8: Sharma A, Gupta NK, Dixit VK. Complexation with phosphatidyl choline as a strategy for absorption enhancement of boswellic acid. Drug Deliv. 2010 Nov;17(8):587-95. doi: 10.3109/10717544.2010.501461. PubMed PMID: 20624027. 9: Di Gregorio GM, Ferraris P, Mariani P. Wetting properties of dioleoyl-phosphatidyl-choline bilayers in the presence of trehalose: an X-ray diffraction study. Chem Phys Lipids. 2010 Jun;163(6):601-6. doi: 10.1016/j.chemphyslip.2010.04.009. Epub 2010 May 8. PubMed PMID: 20435025. 10: Ferderber K, Hook S, Rades T. Phosphatidyl choline-based colloidal systems for dermal and transdermal drug delivery. J Liposome Res. 2009;19(4):267-77. doi: 10.3109/08982100902814006. PubMed PMID: 19863162. 11: Geppert J, Min Y, Neville M, Lowy C, Ghebremeskel K. Gender-specific fatty acid profiles in platelet phosphatidyl-choline and -ethanolamine. Prostaglandins Leukot Essent Fatty Acids. 2010 Jan;82(1):51-6. doi: 10.1016/j.plefa.2009.09.002. Epub 2009 Oct 17. PubMed PMID: 19837573. 12: Peng YN, Ho YL, Wu CY, Liu MY. Investigation of C-reactive protein binding to phosphatidyl choline by CZE and ESI-mass analysis. Electrophoresis. 2009 May;30(9):1564-71. doi: 10.1002/elps.200800608. PubMed PMID: 19425005. 13: Barauskas J, Cervin C, Tiberg F, Johnsson M. Structure of lyotropic self-assembled lipid nonlamellar liquid crystals and their nanoparticles in mixtures of phosphatidyl choline and alpha-tocopherol (vitamin E). Phys Chem Chem Phys. 2008 Nov 21;10(43):6483-5. doi: 10.1039/b811251g. Epub 2008 Sep 29. PubMed PMID: 18979032. 14: Reig F, Sospedra P, Juvé A, Rodriguez L. Interaction of a laminin derived peptide with phosphatidyl choline/phosphatidyl glycerol. Talanta. 2003 Jun 13;60(2-3):591-600. doi: 10.1016/S0039-9140(03)00186-3. PubMed PMID: 18969081. 15: Zhang L, Zhao Y, Yang G. [Determination of benzyl alcohol in polyene phosphatidyl choline injection by GC]. Se Pu. 2007 May;25(3):447-8. Chinese. PubMed PMID: 17679453. 16: Zhou Y, Berry CK, Storer PA, Raphael RM. Peroxidation of polyunsaturated phosphatidyl-choline lipids during electroformation. Biomaterials. 2007 Feb;28(6):1298-306. Epub 2006 Nov 14. PubMed PMID: 17107709. 17: Omoi NO, Arai M, Saito M, Takatsu H, Shibata A, Fukuzawa K, Sato K, Abe K, Fukui K, Urano S. Influence of oxidative stress on fusion of pre-synaptic plasma membranes of the rat brain with phosphatidyl choline liposomes, and protective effect of vitamin E. J Nutr Sci Vitaminol (Tokyo). 2006 Aug;52(4):248-55. PubMed PMID: 17087050. 18: Thirumoorthy K, Nandi N, Vollhardt D, Oliveira ON Jr. Semiempirical quantum mechanical calculations of dipolar interaction between dipyridamole and dipalmitoyl phosphatidyl choline in Langmuir monolayers. Langmuir. 2006 Jun 6;22(12):5398-402. PubMed PMID: 16732669. 19: Huang WD, Zhou DY, Yang YM, Xu ZR, Shen MY, Su W. Changes of dipalmitoyl phosphatidyl choline after mechanical ventilation in patients with acute cerebral injury. Chin J Traumatol. 2006 Jun;9(3):187-9. PubMed PMID: 16723078. 20: Alsina MA, Ortiz A, Polo D, Comelles F, Reig F. Synthesis and study of molecular interactions between phosphatidyl choline and two laminin derived peptides hydrophobically modified. J Colloid Interface Sci. 2006 Feb 15;294(2):385-90. Epub 2005 Sep 8. PubMed PMID: 16153656.