CA major metabolite of 4-HNE
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Labeled Version(s)
90008764-hydroxy Nonenal Glutathione-d3
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4-hydroxy Nonenal Glutathione (trifluoroacetate salt)

Item No. 10627

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
L-γ-glutamyl-S-[(3)-tetrahydro-5-hydroxy-2-pentyl-3-furanyl]-L-cysteinyl-glycine
Synonyms
  • 4-HNE-GSH
Molecular Formula
C19H33N3O8S • CF3COOH
Formula Weight
577.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 10 mg/ml
SMILES
O=C(NCC(O)=O)[C@@H](CSC1CC(O)OC1CCCCC)NC(CC[C@H](N)C(O)=O)=O.FC(F)(C(O)=O)F
InChi Code
InChI=1S/C19H33N3O8S.C2HF3O2/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;3-2(4,5)1(6)7/h11-14,17,26H,2-10,20H2,1H3,(H,21,27)(H,22,23)(H,24,25)(H,28,29);(H,6,7)/t11?,12-,13?,14?,17?;/m1./s1
InChi Key
HORQSLGDIZDKSI-GHGOADBQSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

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    10 mg

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    25 mg

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    Product Description

    4-hydroxy Nonenal Glutathione (HNE-GSH) is a major adduct formed by the reaction of 4-HNE with GSH.1,2,3,4 4-HNE-GSH levels in liver, plasma, or isolated cells can serve as biomarkers for oxidative stress.5 The trapping of 4-HNE by glutathione to give HNE-GSH prevents the formation of DNA adducts with 4-HNE.6,7 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).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. 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).

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

    4. 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).

    5. 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).

    6. 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).

    7. 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).