An internal standard for the quantification of 15-HETE ethyl ester
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15(S)-HETE-d8 ethyl ester

Item No. 30578

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
15(S)-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic-5,6,8,9,11,12,14,15-d8 acid, ethyl ester
Synonyms
  • 15(S)-Hydroxyeicosatetraenoic Acid-d8 ethyl ester
Molecular Formula
C22H28D8O3
Formula Weight
356.6
Purity
≥99% deuterated forms (d1-d8)
Formulation
A 100 µg/ml solution in acetonitrile
Solubility(Learn about Variance in Solubility)
Acetonitrile: 1 mg/mL
λmax
235 nm
SMILES
CCCCC[C@]([2H])(O)/C([2H])=C/C([2H])=C([2H])\C/C([2H])=C([2H])\C/C([2H])=C([2H])\CCCC(OCC)=O
InChi Code
InChI=1S/C22H36O3/c1-3-5-15-18-21(23)19-16-13-11-9-7-6-8-10-12-14-17-20-22(24)25-4-2/h6-7,10-13,16,19,21,23H,3-5,8-9,14-15,17-18,20H2,1-2H3/b7-6-,12-10-,13-11-,19-16+/t21-/m0/s1/i6D,7D,10D,11D,12D,13D,19D,21D
InChi Key
DXWNFRGRLVMUIG-QYYQKCNUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $196

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    50 µg

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    100 µg

    $703

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    Product Description

    15(S)-HETE-d8 ethyl ester is intended for use as an internal standard for the quantification of 15-HETE ethyl ester by GC- or LC-MS. 15(S)-HETE ethyl ester is an esterified form of 15(S)-HETE (Item No. 34720), a major metabolite of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) via the 15-lipoxygenase pathway.1 15(R)-HETE is produced by aspirin-acetylated COX-2 from arachidonic acid, the cytochrome P450 (CYP) isoform CYP2C9, or COX-1 in stimulated human mast cells.2,3,4,5 (±)15-HETE is produced by the non-enzymatic oxidation of arachidonic acid.6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Derogis, P.B.M.C., Chaves-Filho, A.B., and Miyamoto, S. Characterization of hydroxy and hydroperoxy polyunsaturated fatty acids by mass spectrometry. Bioactive lipids in health and disease 21-38 (2019).

    2. Lecomte, M., Laneuville, O., Ji, C., et al. Acetylation of human prostaglandin endoperoxide synthase-2 (cyclooxygenase-2) by aspirin. The Journal of Biological Chemisty 269(18), 13207-13215 (1994).

    3. Capdevila, J.H., Morrow, J.D., Belosludtsev, Y.Y., et al. The catalytic outcomes of the constitutive and the mitogen inducible isoforms of prostaglandin H2 synthase are markedly affected by glutathione and glutathione peroxidase(s). Biochemistry 34, 3325-3337 (1995).

    4. Schneider, C., and Brash, A.R. Stereospecificity of hydrogen abstraction in the conversion of arachidonic acid to 15R-HETE by aspirin-treated cyclooxygenase-2. Implications for the alignment of substrate in the active site. The Journal of Biological Chemisty 275, 4743-4746 (2000).

    5. Bylund, J., Ericsson, J., and Oliw, E.H. Analysis of cytochrome P450 metabolites of arachidonic and linoleic acids by liquid chromatography-mass spectrometry with ion trap MS. Anal. Biochem. 265(1), 55-68 (1998).

    6. Waddington, E.I., Croft, K.D., Sienuarine, K., et al. Fatty acid oxidation products in human atherosclerotic plaque: An analysis of clinical and histopathological correlates. Atherosclerosis 167(1), 111-120 (2003).

    7. Catalá, A. A synopsis of the process of lipid peroxidation since the discovery of the essential fatty acids. Biochem. Biophys. Res. Commun. 399(3), 318-323 (2010).