An activator of PKC and Ras
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Labeled Version(s)
100098721-Stearoyl-2-Arachidonoyl-d8-sn-Glycerol
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1-Stearoyl-2-Arachidonoyl-sn-Glycerol

Item No. 10008650

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid, (1S)-1-(hydroxymethyl)-2-[(1-oxooctadecyl)oxy]ethyl ester
CAS Number
65914-84-3
Synonyms
  • SAG
Molecular Formula
C41H72O5
Formula Weight
645.0
Purity
≥95%
Formulation
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 0.2 mg/mlDMSO: 0.3 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 0.1 mg/ml
SMILES
CCCCCCCCCCCCCCCCCC(=O)OC[C@H](CO)OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC
InChi Code
InChI=1S/C41H72O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,39,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3/b13-11-,19-17-,24-22-
InChi Key
NSXLMTYRMFVYNT-IUJDHQGTSA-N
Side Chain Carbon Sum
38:4
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    5 mg

    $75

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    10 mg

    $143

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    25 mg

    $300

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    Product Description

    Many protein kinase C (PKC) isoforms require activation via second messengers including Ca2+, diacylglycerol (DAG), and/or a phospholipid to phosphorylate target proteins and they initiate a variety of important signalling cascades.1 1-Stearoyl-2-arachidonoyl-sn-glycerol (SAG) is a DAG that contains the ω-6 polyunsaturated fatty acid arachidonic acid in the sn-2 position and stearic acid in the sn-1 position of the glycerol backbone. It can potently activate PKCα, PKCε, and PKCδ at nM concentrations.2 Independent of PKC signalling, SAG competitively binds to the Ras activator RasGRP with a Ki value of 4.49 µM in Jurkat T-cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bell, R.M., and Burns, D.J. Lipid activation of protein kinase C. The Journal of Biological Chemisty 266(8), 4661-4664 (1991).

    2. Madani, S., Hichami, A., Legrand, A., et al. Implication of acyl chain diacylglycerols in activation of different isoforms of protein kinase C. FASEB J. 15(14), 2595-2601 (2001).

    3. Madani, S., Hichami, A., Charkaoui-Malki, M., et al. Diacylglycerols containing ω-3 and ω-6 fatty acids bind to RasGRP and modulate MAP kinase activation. The Journal of Biological Chemisty 279(2), 1176-1183 (2004).