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MedKoo Cat#: 318490 | Name: Phosphatidylserine

Description:

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

Phosphatidylserine is an important phospholipid membrane component which plays a key role in cell cycle signaling, specifically in relationship to apoptosis.Phosphatidylserine is a fatty molecule, a phospholipid, which contains both amino and fatty acids. The fatty acids include omega-3 and omega-6 fatty acid molecules. Phosphatidylserine is widely used as nutritional supplement.

Chemical Structure

Phosphatidylserine
Phosphatidylserine
CAS#51446-62-9

Theoretical Analysis

MedKoo Cat#: 318490

Name: Phosphatidylserine

CAS#: 51446-62-9

Chemical Formula: C42H82NO10P

Exact Mass: 791.5676

Molecular Weight: 792.07

Elemental Analysis: C, 63.69; H, 10.43; N, 1.77; O, 20.20; P, 3.91

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
Phosphatidylserine; Distearoyl phosphatidylserine; Phosphatidylserine(36:0); Dioctadecanoylphosphatidylserine; C42H82NO10P; CHEBI:84519; HMDB12378;
IUPAC/Chemical Name
(2S)-2-amino-3-[[(2R)-2,3-di(octadecanoyloxy)propoxy]-hydroxyphosphoryl]oxypropanoic acid
InChi Key
TZCPCKNHXULUIY-UHFFFAOYSA-N
InChi Code
InChI=1S/C42H82NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(44)50-35-38(36-51-54(48,49)52-37-39(43)42(46)47)53-41(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h38-39H,3-37,43H2,1-2H3,(H,46,47)(H,48,49)
SMILES Code
CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(C(=O)O)N)OC(=O)CCCCCCCCCCCCCCCCC
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, 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 792.07 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: Wesseling MC, Wagner-Britz L, Huppert H, Hanf B, Hertz L, Nguyen DB, Bernhardt I. Phosphatidylserine Exposure in Human Red Blood Cells Depending on Cell Age. Cell Physiol Biochem. 2016 Mar 24;38(4):1376-1390. [Epub ahead of print] PubMed PMID: 27007671. 2: Martin KR, Kantari-Mimoun C, Yin M, Pederzoli-Ribeil M, Angelot-Delettre F, Ceroi A, Grauffel C, Benhamou M, Reuter N, Saas P, Frachet P, Boulanger CM, Witko-Sarsat V. Proteinase 3 is a phosphatidylserine binding protein which affects the production and function of microvesicles. J Biol Chem. 2016 Mar 9. pii: jbc.M115.698639. [Epub ahead of print] PubMed PMID: 26961880. 3: Majumder R, Koklic T, Rezaie AR, Lentz BR. Correction to Phosphatidylserine-Induced Factor Xa Dimerization and Binding to Factor Va Are Competing Processes in Solution. Biochemistry. 2016 Mar 15;55(10):1554. doi: 10.1021/acs.biochem.6b00112. Epub 2016 Mar 4. PubMed PMID: 26943353. 4: Mandaliti W, Nepravishta R, Sinibaldi Vallebona P, Pica F, Garaci E, Paci M. Thymosin α1 Interacts with Exposed Phosphatidylserine in Membrane Models and in Cells and Uses Serum Albumin as a Carrier. Biochemistry. 2016 Mar 15;55(10):1462-72. doi: 10.1021/acs.biochem.5b01345. Epub 2016 Mar 3. PubMed PMID: 26909491. 5: Qadri SM, Donkor DA, Bhakta V, Eltringham-Smith LJ, Dwivedi DJ, Moore JC, Pepler L, Ivetic N, Nazi I, Fox-Robichaud AE, Liaw PC, Sheffield WP. Phosphatidylserine externalization and procoagulant activation of erythrocytes induced by Pseudomonas aeruginosa virulence factor pyocyanin. J Cell Mol Med. 2016 Apr;20(4):710-20. doi: 10.1111/jcmm.12778. Epub 2016 Jan 19. PubMed PMID: 26781477. 6: Officioso A, Alzoubi K, Lang F, Manna C. Hydroxytyrosol inhibits phosphatidylserine exposure and suicidal death induced by mercury in human erythrocytes: Possible involvement of the glutathione pathway. Food Chem Toxicol. 2016 Mar;89:47-53. doi: 10.1016/j.fct.2016.01.003. Epub 2016 Jan 13. PubMed PMID: 26774912. 7: Donyo M, Hollander D, Abramovitch Z, Naftelberg S, Ast G. Phosphatidylserine enhances IKBKAP transcription by activating the MAPK/ERK signaling pathway. Hum Mol Genet. 2016 Apr 1;25(7):1307-17. doi: 10.1093/hmg/ddw011. Epub 2016 Jan 13. PubMed PMID: 26769675. 8: Choi JY, Kumar V, Pachikara N, Garg A, Lawres L, Toh JY, Voelker DR, Ben Mamoun C. Characterization of Plasmodium phosphatidylserine decarboxylase expressed in yeast and application for inhibitor screening. Mol Microbiol. 2016 Mar;99(6):999-1014. doi: 10.1111/mmi.13280. Epub 2015 Dec 22. PubMed PMID: 26585333. 9: Zhang Y, Meng H, Ma R, He Z, Wu X, Cao M, Yao Z, Zhao L, Li T, Deng R, Dong Z, Tian Y, Bi Y, Kou J, Thatte HS, Zhou J, Shi J. CIRCULATING MICROPARTICLES, BLOOD CELLS, AND ENDOTHELIUM INDUCE PROCOAGULANT ACTIVITY IN SEPSIS THROUGH PHOSPHATIDYLSERINE EXPOSURE. Shock. 2016 Mar;45(3):299-307. doi: 10.1097/SHK.0000000000000509. PubMed PMID: 26513704. 10: Varela Chavez C, Haustant GM, Baron B, England P, Chenal A, Pauillac S, Blondel A, Popoff MR. The Tip of the Four N-Terminal α-Helices of Clostridium sordellii Lethal Toxin Contains the Interaction Site with Membrane Phosphatidylserine Facilitating Small GTPases Glucosylation. Toxins (Basel). 2016 Mar 25;8(4). pii: E90. PubMed PMID: 27023605. 11: Zhao L, Bi Y, Kou J, Shi J, Piao D. Phosphatidylserine exposing-platelets and microparticles promote procoagulant activity in colon cancer patients. J Exp Clin Cancer Res. 2016 Mar 25;35(1):54. doi: 10.1186/s13046-016-0328-9. PubMed PMID: 27015840; PubMed Central PMCID: PMC4807543. 12: Bevers EM, Williamson PL. Getting to the Outer Leaflet: Physiology of Phosphatidylserine Exposure at the Plasma Membrane. Physiol Rev. 2016 Apr;96(2):605-45. doi: 10.1152/physrev.00020.2015. Review. PubMed PMID: 26936867. 13: Shiu WL, Huang KR, Hung JC, Wu JL, Hong JR. Knockdown of zebrafish YY1a can downregulate the phosphatidylserine (PS) receptor expression, leading to induce the abnormal brain and heart development. J Biomed Sci. 2016 Feb 29;23(1):31. doi: 10.1186/s12929-016-0248-1. PubMed PMID: 26924789; PubMed Central PMCID: PMC4770675. 14: Birge RB, Boeltz S, Kumar S, Carlson J, Wanderley J, Calianese D, Barcinski M, Brekken RA, Huang X, Hutchins JT, Freimark B, Empig C, Mercer J, Schroit AJ, Schett G, Herrmann M. Phosphatidylserine is a global immunosuppressive signal in efferocytosis, infectious disease, and cancer. Cell Death Differ. 2016 Feb 26. doi: 10.1038/cdd.2016.11. [Epub ahead of print] Review. PubMed PMID: 26915293. 15: Stokes CA, Kaur R, Edwards MR, Mondhe M, Robinson D, Prestwich EC, Hume RD, Marshall CA, Perrie Y, O'Donnell VB, Harwood JL, Sabroe I, Parker LC. Human rhinovirus-induced inflammatory responses are inhibited by phosphatidylserine containing liposomes. Mucosal Immunol. 2016 Feb 24. doi: 10.1038/mi.2015.137. [Epub ahead of print] PubMed PMID: 26906404. 16: Fujieda Y, Amengual O, Matsumoto M, Kuroki K, Takahashi H, Kono M, Kurita T, Otomo K, Kato M, Oku K, Bohgaki T, Horita T, Yasuda S, Maenaka K, Hatakeyama S, Nakayama KI, Atsumi T. Ribophorin II is involved in the tissue factor expression mediated by phosphatidylserine-dependent antiprothrombin antibody on monocytes. Rheumatology (Oxford). 2016 Feb 19. pii: kew005. [Epub ahead of print] PubMed PMID: 26895716. 17: Fernandez-Arias C, Rivera-Correa J, Gallego-Delgado J, Rudlaff R, Fernandez C, Roussel C, Götz A, Gonzalez S, Mohanty A, Mohanty S, Wassmer S, Buffet P, Ndour PA, Rodriguez A. Anti-Self Phosphatidylserine Antibodies Recognize Uninfected Erythrocytes Promoting Malarial Anemia. Cell Host Microbe. 2016 Feb 10;19(2):194-203. doi: 10.1016/j.chom.2016.01.009. PubMed PMID: 26867178. 18: Cheng X, Li L, Thorpe PE, Yopp AC, Brekken RA, Huang X. Antibody-Mediated Blockade of Phosphatidylserine Enhances the Antitumor Effect of Sorafenib in Hepatocellular Carcinomas Xenografts. Ann Surg Oncol. 2016 Feb 4. [Epub ahead of print] PubMed PMID: 26847681. 19: Li YH, Yu SL, Gan XG, Pan SH, Teng YQ, An RH. Externalization of phosphatidylserine via multidrug resistance 1 (MDR1)/P-glycoprotein in oxalate-treated renal epithelial cells: implications for calcium oxalate urolithiasis. Int Urol Nephrol. 2016 Feb;48(2):175-81. doi: 10.1007/s11255-015-1155-1. Epub 2015 Nov 11. PubMed PMID: 26560472. 20: Nagata S, Suzuki J, Segawa K, Fujii T. Exposure of phosphatidylserine on the cell surface. Cell Death Differ. 2016 Feb 19. doi: 10.1038/cdd.2016.7. [Epub ahead of print] Review. PubMed PMID: 26891692.

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