MedKoo Cat#: 530783 | Name: Myristoyllysophosphatidylcholine

Description:

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

Myristoyllysophosphatidylcholine is a bioactive chemical.

Chemical Structure

Myristoyllysophosphatidylcholine
Myristoyllysophosphatidylcholine
CAS#13699-45-1

Theoretical Analysis

MedKoo Cat#: 530783

Name: Myristoyllysophosphatidylcholine

CAS#: 13699-45-1

Chemical Formula: C22H46NO7P

Exact Mass: 467.3012

Molecular Weight: 467.58

Elemental Analysis: C, 56.51; H, 9.92; N, 3.00; O, 23.95; P, 6.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Myristoyllysophosphatidylcholine
IUPAC/Chemical Name
3,5,9-Trioxa-4-phosphatricosan-1-aminium, 4,7-dihydroxy-N,N,N-trimethyl-10-oxo-, inner salt, 4-oxide
InChi Key
VXUOFDJKYGDUJI-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3
SMILES Code
CCCCCCCCCCCCCC(OCC(O)COP(OCC[N+](C)(C)C)([O-])=O)=O
Appearance
Solid powder
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
Shelf Life
>3 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 467.58 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.

Recalculate based on batch purity %
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
1: Klapper Y, Maffre P, Shang L, Ekdahl KN, Nilsson B, Hettler S, Dries M, Gerthsen D, Nienhaus GU. Low affinity binding of plasma proteins to lipid-coated quantum dots as observed by in situ fluorescence correlation spectroscopy. Nanoscale. 2015 Jun 14;7(22):9980-4. doi: 10.1039/c5nr01694k. Epub 2015 May 15. PubMed PMID: 25975280. 2: Rzehak P, Hellmuth C, Uhl O, Kirchberg FF, Peissner W, Harder U, Grote V, Weber M, Xhonneux A, Langhendries JP, Ferre N, Closa-Monasterolo R, Verduci E, Riva E, Socha P, Gruszfeld D, Koletzko B; European Childhood Obesity Trial Study Group. Rapid growth and childhood obesity are strongly associated with lysoPC(14:0). Ann Nutr Metab. 2014;64(3-4):294-303. doi: 10.1159/000365037. Epub 2014 Oct 2. PubMed PMID: 25300273. 3: Huang Q, Li Q, Joy J, Chen AS, Ruiz-Carrillo D, Hill J, Lescar J, Kang C. Lyso-myristoyl phosphatidylcholine micelles sustain the activity of Dengue non-structural (NS) protein 3 protease domain fused with the full-length NS2B. Protein Expr Purif. 2013 Dec;92(2):156-62. doi: 10.1016/j.pep.2013.09.015. Epub 2013 Sep 29. PubMed PMID: 24084007. 4: Koehler J, Sulistijo ES, Sakakura M, Kim HJ, Ellis CD, Sanders CR. Lysophospholipid micelles sustain the stability and catalytic activity of diacylglycerol kinase in the absence of lipids. Biochemistry. 2010 Aug 24;49(33):7089-99. doi: 10.1021/bi100575s. PubMed PMID: 20666483; PubMed Central PMCID: PMC2923640. 5: Galka JJ, Baturin SJ, Manley DM, Kehler AJ, O'Neil JD. Stability of the glycerol facilitator in detergent solutions. Biochemistry. 2008 Mar 18;47(11):3513-24. doi: 10.1021/bi7021409. Epub 2008 Feb 20. PubMed PMID: 18284214. 6: Wagner K, Desbat B, Brezesinski G. Liquid-liquid immiscibility in model membranes activates secretory phospholipase A2. Biochim Biophys Acta. 2008 Jan;1778(1):166-74. Epub 2007 Oct 16. PubMed PMID: 17964533. 7: Peric M, Alves M, Bales BL. Combining precision spin-probe partitioning with time-resolved fluorescence quenching to study micelles. Application to micelles of pure lysomyristoylphosphatidylcholine (LMPC) and LMPC mixed with sodium dodecyl sulfate. Chem Phys Lipids. 2006 Jul;142(1-2):1-13. Epub 2006 Feb 28. PubMed PMID: 16569402. 8: Blein JP, Coutos-Thévenot P, Marion D, Ponchet M. From elicitins to lipid-transfer proteins: a new insight in cell signalling involved in plant defence mechanisms. Trends Plant Sci. 2002 Jul;7(7):293-6. PubMed PMID: 12119165. 9: Douliez JP, Jégou S, Pato C, Mollé D, Tran V, Marion D. Binding of two mono-acylated lipid monomers by the barley lipid transfer protein, LTP1, as viewed by fluorescence, isothermal titration calorimetry and molecular modelling. Eur J Biochem. 2001 Jan;268(2):384-8. PubMed PMID: 11168373. 10: Werbovetz KA, Bacchi CJ, Englund PT. Trypanocidal analogs of myristate and myristoyllysophosphatidylcholine. Mol Biochem Parasitol. 1996 Oct 18;81(1):115-8. PubMed PMID: 8892311. 11: Werbovetz KA, Englund PT. Lipid metabolism in Trypanosoma brucei: utilization of myristate and myristoyllysophosphatidylcholine for myristoylation of glycosyl phosphatidylinositols. Biochem J. 1996 Sep 1;318 ( Pt 2):575-81. PubMed PMID: 8809049; PubMed Central PMCID: PMC1217659. 12: Yuan P, Fisher PJ, Prendergast FG, Kemple MD. Structure and dynamics of melittin in lysomyristoyl phosphatidylcholine micelles determined by nuclear magnetic resonance. Biophys J. 1996 May;70(5):2223-38. PubMed PMID: 9172746; PubMed Central PMCID: PMC1225197. 13: Bowes AE, Samad AH, Jiang P, Weaver B, Mellors A. The acquisition of lysophosphatidylcholine by African trypanosomes. J Biol Chem. 1993 Jul 5;268(19):13885-92. PubMed PMID: 8314756. 14: Milne TJ, Atkins AR, Warren JA, Auton WP, Smith R. Shark myelin basic protein: amino acid sequence, secondary structure, and self-association. J Neurochem. 1990 Sep;55(3):950-5. PubMed PMID: 1696624. 15: Petersheim M, Halladay HN, Blodnieks J. Tb3+ and Ca2+ binding to phosphatidylcholine. A study comparing data from optical, NMR, and infrared spectroscopies. Biophys J. 1989 Sep;56(3):551-7. PubMed PMID: 2790138; PubMed Central PMCID: PMC1280508. 16: Gow A, Smith R. The thermodynamically stable state of myelin basic protein in aqueous solution is a flexible coil. Biochem J. 1989 Jan 15;257(2):535-40. PubMed PMID: 2467658; PubMed Central PMCID: PMC1135611. 17: Dempsey CE, Watts A. A deuterium and phosphorus-31 nuclear magnetic resonance study of the interaction of melittin with dimyristoylphosphatidylcholine bilayers and the effects of contaminating phospholipase A2. Biochemistry. 1987 Sep 8;26(18):5803-11. PubMed PMID: 3676290. 18: Gow A, Winzor DJ, Smith R. Equilibrium binding of myristoyllysophosphatidylcholine to bovine myelin basic protein: an example of ligand-mediated acceptor association. Biochemistry. 1987 Feb 24;26(4):982-7. PubMed PMID: 2436660. 19: Ellerbe P, Murphy RB, Rose HG. Lecithin:cholesterol acyltransferase regulation. Effect of fluidity of dimyristoylphosphatidylcholine vesicles. Biochim Biophys Acta. 1985 Jul 25;817(2):282-8. PubMed PMID: 4016106. 20: Smith R. The encephalitogenic protein of myelin forms hexamers in which the polypeptides have a pleated-sheet structure. FEBS Lett. 1985 Apr 22;183(2):331-4. PubMed PMID: 2580739.