A monohydroxy fatty acid
Related Products
Enantiomer(s)
3472015(S)-HETE
Isomer(s)
34700(±)15-HETE
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15(R)-HETE

Item No. 34710

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
15R-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid
CAS Number
83603-31-0
Synonyms
  • 15(R)-Hydroxyeicosatetraenoic Acid
Molecular Formula
C20H32O3
Formula Weight
320.5
Purity
≥98%
Formulation (Request formulation change)
A 100 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS pH 7.2: 0.8 mg/ml
λmax
236 nm
SMILES
CCCCC[C@@H](O)\C=C\C=C\C/C=C\C/C=C\CCCC(=O)O
InChi Code
InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m1/s1
InChi Key
JSFATNQSLKRBCI-UDQWCNDOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    25 µg

    $156

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    50 µg

    $294

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    100 µg

    $432

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    Product Description

    15(R)-HETE is a monohydroxy fatty acid. It is produced by aspirin-acetylated COX-2 from arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) and converted into the specialized pro-resolving mediator 15(R)-lipoxin A4 (Item No. 90415) and 15(R)-lipoxin B4 in a transcellular process via 5-lipoxygenase (5-LO).1,2,3,4,5 It is also produced by the cytochrome P450 (CYP) isoform CYP2C9.1,2,3,6 15(R)-HETE can also be formed from arachidonic acid by COX-1 in stimulated human mast cells and accumulates because, unlike 15(S)-HETE (Item No. 34720), it is not converted to 15-KETE (15-OxoETE; Item No. 34730) by 15-hydroxyprostaglandin dehydrogenase (15-PGDH).7 It is an agonist of PPARβ/δ, inducing expression of a PPARβ/δ target gene in a reporter assay using NIH3T3 cells.8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).

    3. 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).

    4. Clària, J., and Serhan, C.N. Aspirin triggers previously undescribed bioactive eicosanoids by human endothelial cell-leukocyte interactions. PNAS USA 92(21), 9475-9479 (1995).

    5. Serhan, C.N., Hamberg, M., Samuelsson, B., et al. On the stereochemistry and biosynthesis of lipoxin B. Proc. Natl. Acad. Sci. USA 83(7), 1983-1987 (1986).

    6. 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).

    7. Johnsson, A.-K., Rönnberg, E., Fuchs, D., et al. COX-1 dependent biosynthesis of 15-hydroxyeicosatetraenoic acid in human mast cells. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1866(5), 158886 (2021).

    8. Naruhn, S., Meissner, W., Adhikary, T., et al. 15-hydroxyeicosatetraenoic acid is a preferential peroxisome proliferator-activated receptor β/δ agonist. Mol. Pharmacol. 77(2), 171-184 (2010).

    Product Citations

    Mainka, M., George, S., Angioni, C., et al. On the biosynthesis of specialized pro-resolving mediators in human neutrophils and the influence of cell integrit. Biochim. Biophys. Acta Mol. Cell Biol. Lipids 1867(3), 159093 (2022).