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P5660

Sigma-Aldrich

3-sn-Phosphatidyl-L-serine sodium salt from bovine brain

≥95% (TLC)

Synonym(s):
L-α-Phosphatidyl-L-serine sodium salt, 1,2-Diacyl-sn-glycero-3-phospho-L-serine
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥95% (TLC)

storage temp.

−20°C

SMILES string

[Na+].CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C([O-])=O)OC(=O)CCCCCCCCCCCCCCCCC

InChI

1S/C42H82NO10P.Na/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);/q;+1/p-1/t38-,39+;/m1./s1

InChI key

SJRBMGBLPUBGJL-MBAWARMDSA-M

General description

Phosphatidylserine is an anionic phospholipid, which is found on the plasma membrane. Exposure of phosphatidylserine on the surface of plasma membrane stimulates the removal of apoptotic and red blood cells. It regulates the production of thrombin and maintains hemostasis.

Application

3-sn-Phosphatidyl-L-serine sodium salt from bovine brain has been used as a glycosylphosphatidylinositol (GPI)-anchor control.

Packaging

5, 25, 100 mg in ampule

Biochem/physiol Actions

A slowly metabolized structural phospholipid found mainly in gray matter.

Caution

Solutions exposed to room temperature will decompose about 0.5% per day.

Preparation Note

Washed with EDTA and converted to a sodium salt.

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is the molecular weight of Product P5660, 3-sn-Phosphatidyl-L-serine sodium salt from bovine brain?

    The molecular weight of this compound is approximately 812.1 g/mole. This molecular weight assumes that stearoyl and oleoyl are the prodimant fatty acids in the compound.  Phosphatidylserine may have a number of different fatty acid residues associated with it.  Our analyses of multiple lots of phosphatidylserine identified average fatty acid percentages of approximately 40% for stearic acid and 30% for oleic acid.

  4. What is Product P5660, 3-sn-Phosphatidyl-L-serine sodium salt from bovine brain, soluble in?

    This product is soluble in chloroform:methanol (95:5 v/v) at a concentration of 50 mg/mL. It will likely form a suspension or emulsion in deionized water at a concentration of 1 mg/mL or higher.

  5. What is the solution stability of Product P5660, 3-sn-Phosphatidyl-L-serine sodium salt from bovine brain?

    Solutions can be divided into aliquots and stored at -20 °C. We have no information as to how long the solutions will be stable. Solution stability is enhanced when the compound is protected from oxygen, because the unsaturated fatty acids are subject to oxidation. To protect from oxidation, dissolve the compound in solvents in which oxygen has been removed and replaced with an inert gas such as nitrogen or argon.

  6. Is 3-sn-Phosphatidyl-L-serine sodium salt from bovine brain available in solution?

    Yes. Product No. P6641 is a ready-to-use solution of phosphatidylserine in a chloroform:methanol mixture.

  7. Do you have any inhibitors for Protein Kinase C (PKC)?

    Yes. Two examples are Product No. C6303 (Calphostin C from Cladosporium cladosporioides) and Product No. C2932 (Chelerythrine chloride).

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. What is Product P5660, 3-sn-Phosphatidyl-L-serine sodium salt, commonly used for?

    Phosphatidylserine is important in enzymatic assays of purified protein kinase C. During activation of this enzyme, as part of the signal transduction process, phosphatidylserine, which is located on the inside of cellular plasma membranes, binds to cysteine residue domains on protein kinase C. Phosphatidylserine can be used as a standard in thin-layer chromatography and for artificial membrane studies such as in lipsome research.

  11. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Phosphatidylserine exposure during apoptosis is a cell-type-specific event and does not correlate with plasma membrane phospholipid scramblase expression
Fadeel B, et al.
Biochemical and Biophysical Research Communications, 266(2), 504-511 (1999)
Exposure of platelet membrane phosphatidylserine regulates blood coagulation
Lentz BR
Progress in Lipid Research, 42(5), 423-438 (2003)
TIMP-1-GPI in combination with hyperthermic treatment of melanoma increases sensitivity to FAS-mediated apoptosis
Djafarzadeh R, et al.
Cancer Immunology, Immunotherapy, 58(3), 361-361 (2009)
The role of phosphatidylserine in recognition and removal of erythrocytes.
Kuypers FD
Cellular and molecular biology (Noisy-le-Grand, France), 50(2), 147-158 (2004)
Julien Perino et al.
Antiviral research, 89(1), 89-97 (2010-11-26)
Vaccinia virus (VACV) was used as a surrogate of Variola virus (genus Orthopoxvirus), the causative agent of smallpox, to study orthopoxvirus infection via the respiratory airway. Lung surfactant, a physiological barrier to infection encountered by the virus, is predominantly composed...

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