An internal standard for the quantification of 1-stearoyl-2-arachidonoyl-sn-glycerol
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Unlabeled Version(s)
100086501-Stearoyl-2-Arachidonoyl-sn-Glycerol
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1-Stearoyl-2-Arachidonoyl-d8-sn-Glycerol

Item No. 10009872

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoic-5,6,8,9,11,12,14,15-d8 acid, (1S)-1-(hydroxymethyl)-2-[(1-oxooctadecyl)oxy]ethyl ester
CAS Number
2692624-31-8
Synonyms
  • SAG-d8
Molecular Formula
C41H64D8O5
Formula Weight
653.1
Purity
≥99% deuterated forms (d1-d8)
Formulation
A 1 mg/ml solution in acetonitrile
Solubility(Learn about Variance in Solubility)
Ethanol: 30 mg/mlEthanol:PBS (pH 7.2) (1:2): 0.3 mg/ml
SMILES
OC[C@H](OC(CCC/C([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\CCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O
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-,30-28-/t39-/m0/s1/i11D,13D,17D,19D,22D,24D,28D,30D
InChi Key
NSXLMTYRMFVYNT-YVJRVKRGSA-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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    100 µg

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    1 mg

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    Product Description

    1-Stearoyl-2-arachidonoyl-d8-sn-glycerol (SAG-d8) is intended for use as an internal standard for the quantification of SAG (Item No. 10008650) by GC- or LC-MS. Many protein kinase C (PKC) isoforms require activation via second messengers including Ca2+, diacylglycerol (DAG), and/or a phospholipid in order to phosphorylate target proteins, initiating a variety of important signaling 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, ε, and δ at nM concentrations.2 Independent of PKC signaling, 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. The FASEB Journal 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).

    Product Citations

    Tufail, Y.Z., Guijas, C., Kummer, D.A., et al. Suppression of pain transmission and behavior by inhibition of peripheral diacylglycerol metabolism. Cell Chem. Bio. 33(1), 74-90.e19 (2025).