Deuterated standard for 4-HNE-GSH
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4-hydroxy Nonenal Glutathione-d3

Item No. 9000876

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N5-((2R)-1-((carboxymethyl)amino)-3-(((3S)-5-hydroxy-2-(pentyl-5,5,5-d3)tetrahydrofuran-3-yl)thio)-1-oxopropan-2-yl)-D-glutamine
Synonyms
  • 4-HNE-GSH-d3
Molecular Formula
C19H30D3N3O8S
Formula Weight
466.6
Purity
≥99% deuterated forms (d1-d3)
Formulation
A lyophilized powder
Solubility(Learn about Variance in Solubility)
Water: 10 mg/ml
SMILES
O=C(NCC(O)=O)[C@H](CS[C@H]1CC(O)OC1CCCCC([2H])([2H])[2H])NC(CC[C@@H](N)C(O)=O)=O
InChi Code
InChI=1S/C19H33N3O8S/c1-2-3-4-5-13-14(8-17(26)30-13)31-10-12(18(27)21-9-16(24)25)22-15(23)7-6-11(20)19(28)29/h11-14,17,26H,2-10,20H2,1H3,(H,21,27)(H,22,23)(H,24,25)(H,28,29)/t11-,12+,13?,14+,17?/m1/s1/i1D3
InChi Key
ICRIFHIWWXQBPY-KXAYWLRFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    50 µg

    $135

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    100 µg

    $256

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    500 µg

    $1,069

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    1 mg

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    Product Description

    4-hydroxy Nonenal Glutathione-d3 (4-HNE-GSH-d3) is intended for use as an internal standard for the quantification of 4-HNE-GSH by GC- or LC-MS. 4-hydroxy-Nonenal (4-HNE) is a major aldehyde produced during the lipid peroxidation of ω-6 polyunsaturated fatty acids, such as arachidonic acid and linoleic acid.1,2 4-HNE-GSH is a major adduct formed by the reaction of 4-HNE with GSH.3,4,5,6 4-HNE-GSH levels in liver, plasma, or isolated cells can serve as biomarkers for oxidative stress.7 The trapping of 4-HNE by glutathione to give HNE-GSH prevents the formation of DNA adducts with 4-HNE.8,9 In human polymorphonuclear leukocytes, HNE-GSH is metabolized to 1,4-dihydroxynonene glutathione (DHN-GSH), 4-hydroxynonenoic acid glutathione (HNA-GSH), and 4-hydroxy nonenal mercapturic acid (HNE-MA).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pryor, W.A., and Porter, N.A. Suggested mechanisms for the production of 4-hydroxy-2-nonenal from the autoxidation of polyunsaturated fatty acids. Free Radic. Biol. Med. 8(6), 541-543 (1990).

    2. Esterbauer, H., Schaur, R.J., and Zoliner, H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde, and related aldehydes. Free Radic. Biol. Med. 11(1), 81-128 (1991).

    3. Siems, W., Crifo, C., Capuozzo, E., et al. Metabolism of 4-hydroxy-2-nonenal in human polymorphonuclear leukocytes. Arch. Biochem. Biophys. 503(2), 248-252 (2010).

    4. Laurent, A., Alary, J., Debrauwer, L., et al. Analysis in the rat of 4-hydroxynonenal metabolites excreted in bile: Evidence of enterohepatic circulation of these byproducts of lipid peroxidation. Chem. Res. Toxicol. 12(10), 887-894 (1999).

    5. Siems, W., and Grune, T. Intracellular metabolism of 4-hydroxynonenal. Mol. Aspects Med. 24(4-5), 167-175 (2003).

    6. Alary, J., Fernandez, Y., Debrauwer, L., et al. Identification of intermediate pathways of 4-hydroxynonenal metabolism in the rat. Chem. Res. Toxicol. 16(3), 320-327 (2003).

    7. Völkel, W., Alvarez-Sánchez, R., Weick, I., et al. Glutathione conjugates of 4-hydroxy-2(E)-nonenal as biomarkers of hepatic oxidative stress-induced lipid peroxidation in rats. Free Radic. Biol. Med. 38(11), 1526-1536 (2005).

    8. King, A.O., Corley, E.G., Anderson, R.K., et al. An efficient synthesis of LTD4 antagonist L-699,392. The Journal of Organic Chemistry 58(14), 3731-3735 (1993).

    9. Falletti, O., Cadet, J., Favier, A., et al. Trapping of 4-hydroxynonenal by glutathione efficiently prevents formation of DNA adducts in human cells. Free Radic. Biol. Med. 42(8), 1258-1269 (2007).