Phosphatidyl choline (from Soybean)

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

MedKoo CAT#: 510262A

CAS#: 8002-43-5 (from Soybean)

Description: 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.


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500g
USD 3850
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1kg
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Cat#510262A - Phosphatidyl choline (from soybean), purity >98%, is in stock. Minimum 500g order is requested for this item. Current shipping out time is about 10 days after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international)


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 510262A
Name: Phosphatidyl choline (from Soybean)
CAS#: 8002-43-5 (from Soybean)
Chemical Formula: N/A (mixture)
Exact Mass: 0.0
Molecular Weight: 0.0
Elemental Analysis: N/A (mixture)


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


Technical Data

Appearance:
Yellow to light brown semi-solid or wax solid.

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

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


Additional Information

Related CAS#
8002-43-5 ( Phosphatidyl cholinefrom Soybean);
8057-53-2 ( Phosphatidyl choline from egg yolk)

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) 
  
 
 


References

 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.