4-hydroxy Nonenal Glutathione (trifluoroacetate salt)

Cayman Chemical Item Number 10627

4-HNE-GSH

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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

1. Siems, W., Crifo, C., Capuozzo, E., et al. Metabolism of 4-hydroxy-2-nonenal in human polymorphonuclear leukocytes. Arch Biochem Biophys 503 248-252 (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 12 887-894 (1999).

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

4. Alary, J., Fernandez, Y., Debrauwer, L., et al. Identification of intermediate pathways of 4-hydroxynonenal metabolism in the rat. Chem Res Toxicol 16 320-327 (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 1526-1536 (2005).

6. King, A.O., Corley, E.G., Anderson, R.K., et al. An efficient synthesis of LTD4 antagonist L-699,392. J Org Chem 58 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 1258-1269 (2007).

Synonyms
  • 4-HNE-GSH
Formal Name L-​γ-​glutamyl-​S-​[(3)-​tetrahydro-​5-​hydroxy-​2-​pentyl-​3-​furanyl]-​L-​cysteinyl-​glycine
Molecular Formula C19H33N3O8S • CF3COOH
Formula Weight 577.6
Formulation A crystalline solid
Purity ≥95%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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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
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​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
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HORQSLGDIZDKSI-GHGOADBQSA-N

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Size Price Quantity Subtotal
1 mg $53.00 $0.00
5 mg $239.00 $0.00
10 mg $424.00 $0.00
25 mg $928.00 $0.00
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Cart Total $0.00

Pricing updated 2015-07-28. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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Ann Arbor, Michigan 48108 USA

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