A metabolite of 4-HNE
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Labeled Version(s)
90003484-hydroxy Nonenal Mercapturic Acid-d3
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4-hydroxy Nonenal Mercapturic Acid

Item No. 32110

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-acetyl-S-(tetrahydro-5-hydroxy-2-pentyl-3-furanyl)-L-cysteine
CAS Number
146764-24-1
Molecular Formula
C14H25NO5S
Formula Weight
319.4
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 50 mg/mlPBS pH 7.2: 0.1 mg/ml
SMILES
CCCCCC1OC(O)CC1SC[C@H](NC(=O)C)C(=O)O
InChi Code
InChI=1S/C14H25NO5S/c1-3-4-5-6-11-12(7-13(17)20-11)21-8-10(14(18)19)15-9(2)16/h10-13,17H,3-8H2,1-2H3,(H,15,16)(H,18,19)
InChi Key
DEWNQQSQBYUUAE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

    $91

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    5 mg

    $382

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    10 mg

    $674

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    Product Description

    Peroxidation of common ω-6 polyunsaturated fatty acids (PUFAs) such as linoleic acid, DGLA, and arachidonic acid can give rise to 4-HNE. 4-HNE is cleared rapidly from the plasma and undergoes enterohepatic circulation as a glutathione conjugate in the rat.1 About two thirds of an administered dose of 4-HNE is excreted within 48 hours in the urine, primarily in the form of mercapturic acid conjugates.2 The C-1 aldehyde of 4-HNE is reduced to an alcohol in about half of these metabolites. The remainder are C-1 aldehydes or have been oxidized to C-1 carboxylic acids. These aldehydes and carboxylic acids can also form γ-lactols and γ-lactones, respectively, producing at least 4 or 5 end urinary metabolites of 4-HNE in vivo.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Alary, J., Bravais, F., Cravedi, J.P., et al. Mercapturic acid conjugates as urinary end metabolites of the lipid peroxidation product 4-hydroxy-2-nonenal in the rat. Chem. Res. Toxicol. 8, 34-39 (1995).