An internal standard for the quantification of 1-stearoyl-2-arachidonoyl-sn-glycero-3-PC
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1-Stearoyl-2-Arachidonoyl-d11-sn-glycero-3-PC

Item No. 27928

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(R)-2-(((5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl-16,16,17,17,18,18,19,19,20,20,20-d11)oxy)-3-(stearoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
Synonyms
  • 18:0/20:4-d11-PC
  • PC(18:0/20:4-d11)
  • SAPC-d11
  • 1-Stearoyl-2-Arachidonoyl-d11-sn-glycero-3-Phosphatidylcholine
  • 1-Stearoyl-2-Arachidonoyl-d11-sn-glycero-3-Phosphocholine
Molecular Formula
C46H73D11NO8P
Formula Weight
821.2
Purity
≥99% deuterated forms (d1-d11)
Formulation
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
Ethanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:2): 0.3 mg/ml
SMILES
O=C(CCCCCCCCCCCCCCCCC)OC[C@@H](OC(CCC/C=C\C/C=C\C/C=C\C/C=C\C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])C([2H])([2H])[2H])=O)COP([O-])(OCC[N+](C)(C)C)=O
InChi Code
InChI=1S/C46H84NO8P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-35-37-39-46(49)55-44(43-54-56(50,51)53-41-40-47(3,4)5)42-52-45(48)38-36-34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h14,16,20,22,25,27,31,33,44H,6-13,15,17-19,21,23-24,26,28-30,32,34-43H2,1-5H3/b16-14-,22-20-,27-25-,33-31-/t44-/m1/s1/i1D3,6D2,8D2,10D2,12D2
InChi Key
PSVRFUPOQYJOOZ-NIGIQULMSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $41

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    50 µg

    $72

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    100 µg

    $127

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    Product Description

    1-Stearoyl-2-arachidonoyl-d11-sn-glycero-3-PC (SAPC-d11) is intended for use as an internal standard for the quantification of 1-stearoyl-2-arachidonoyl-sn-glycero-3-PC (Item No. 10009864) by GC- or LC-MS. SAPC is a phospholipid containing stearic acid (Item No. 10011298) and arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) at the sn-1 and sn-2 positions, respectively. It is a component of LDL and has been found in human stenotic aortic valves and atherosclerotic plaques.1,2 Levels of SAPC are increased in the subepithelial invasive region compared to the superficial region of tumor tissue samples from patients with superficial-type pharyngeal squamous cell carcinoma.3 SAPC unilamellar vesicles have been used as substrates to quantify the activity of secretory phospholipase A2 (sPLA2) in the presence or absence of inhibitors.4 SAPC has also been used in the formation of lipid bilayers to study the effects of lipid composition on bilayer phase transitions.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Milne, G.L., Seal, J.R., Havrilla, C.M., et al. Identification and analysis of products formed from phospholipids in the free radical oxidation of human low density lipoproteins. J. Lipid Res. 46(2), 307-319 (2005).

    2. Lehti, S., Käkelä, R., Hörkkö, S., et al. Modified lipoprotein-derived lipid particles accumulate in human stenotic aortic valves. PLoS One 8(6), e65810 (2013).

    3. Ishikawa, S., Tateya, I., Hayasaka, T., et al. The distribution of phosphatidylcholine species in superficial-type pharyngeal carcinoma. Biomed. Res. Int. 5387913, (2017).

    4. Schebb, N.H., Falck, D., Faber, H., et al. Fast method for monitoring phospholipase A2 activity by liquid chromatography-electrospray ionization mass spectrometry. J. Chromatogr. A 1216(27), 5249-5255 (2009).

    5. Tada, K., Goto, M., Tamai, N., et al. Pressure effect on the bilayer phase transition of asymmetric lipids with an unsaturated acyl chain. Ann. N. Y. Acad. Sci. 1189(1), 77-85 (2010).