An internal standard for the quantification of 12-HETE
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Unlabeled Version(s)
3457012(S)-HETE
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12(S)-HETE-d8

Item No. 334570

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
12S-hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic-5,6,8,9,11,12,14,15-d8 acid
CAS Number
84807-90-9
Synonyms
  • 12(S)-Hydroxyeicosatetraenoic Acid-d8
Molecular Formula
C20H24D8O3
Formula Weight
328.5
Purity
≥99% deuterated forms (d1-d8)
Formulation
A 100 µg/ml solution in acetonitrile
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 2 mg/mlDMF: MiscibleDMSO: MiscibleEthanol: MisciblePBS pH 7.2: 0.8 mg/ml
λmax
237 nm
SMILES
[2H]/C(C/C([2H])=C([2H])\CCCC(O)=O)=C([2H])/C=C([2H])/[C@](O)([2H])C/C([2H])=C([2H])\CCCCC
InChi Code
InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1/i7D,8D,9D,10D,11D,13D,17D,19D
InChi Key
ZNHVWPKMFKADKW-OPXGWVKSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    25 µg

    $208

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    50 µg

    $395

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    100 µg

    $748

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    Product Description

    12(S)-HETE-d8 is intended for use as an internal standard for the quantification of 12-HETE by GC- or LC-MS. (±)12-HETE is formed via non-enzymatic oxidation of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607).1,2 12(S)- and 12(R)-HETE are formed by 12(S)- and 12(R)-lipoxygenase-mediated oxidation of arachidonic acid, respectively.3,4 12(R)-HETE can also be formed by oxidation of arachidonic acid mediated by cytochrome P450s (CYP450s).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Powell, W.S., and Rokach, J. Biosynthesis, biological effects, and receptors of hydroxyeicosatetraenoic acids (HETEs) and oxoeicosatetraenoic acids (oxo-ETEs) derived from arachidonic acid. Biochim. Biophys. Acta 1851(4), 340-355 (2014).

    2. 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).

    3. Kühn, H., Banthiya, S., and van Leyen, K. Mammalian lipoxygenases and their biological relevance. Biochim. Biophys. Acta 1851(4), 308-330 (2015).

    4. Bürger, F., Krieg, P., Marks, F., et al. Positional- and stereo-selectivity of fatty acid oxygenation catalysed by mouse (12S)-lipoxygenase isoenzymes. Biochem J. 348(Pt 2), 329-335 (2000).

    Product Citations

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    Lin, N., Shay, J.E.S., Xie, H., et al. Myeloid cell hypoxia-inducible factors promote resolution of inflammation in experimental colitis. Front. Immunol. 9(2565), (2018).

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).

    Rhodes, L.E., Gledhill, K., Masoodi, M., et al. The sunburn response in human skin is characterized by sequential eicosanoid profiles that may mediate its early and late phases. The FASEB Journal 23(11), 3947-3956 (2009).