4-hydroxy Nonenal Mercapturic Acid-d₃ Exclusive

Cayman Chemical Item Number 9000348

4-hydroxy Nonenal Mercapturic Acid-d3

See more	Oxylipins (227) Oxidative Injury (291)

Description

4-hydroxy Nonenal mercapturic acid-d₃ contains three deuterium atoms at the terminal methyl position. It is intended for use as an internal standard for the quantification of 4-HNE mercapturic acid by GC- or LC-mass spectrometry. 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 four or five end urinary metabolites of 4-HNE in vivo.

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 12 887-894 (1999).

2 Alary, J., Bravais, F., Cravedi, J., 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).

Formal Name	N-acetyl-S-(tetrahydro-5-hydroxy-2-pentyl-3-furanyl)-L-cysteine-11,11,11-d3
Molecular Formula	C₁₄H₂₂D₃NO₅S
Formula Weight	322.4
Formulation	A solution in ethanol
Purity	≥99% deuterated forms (d1-d3)
Stability	1 year
Storage	-80°C
Shipping	Dry ice in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CCCCCC1OC(O)CC1SC[C@H](NC(=O)C)C(=O)O

Background Reading

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 8 541-543 (1990).

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).

Alary, J., Bravais, F., Cravedi, J., 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).

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100 µg	See a distributor in your region for pricing
500 µg	See a distributor in your region for pricing
1 mg	See a distributor in your region for pricing

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Batch-specific Information

FAQs

It appears that there is a heterogenous mixture of deuterated species in your deuterated standards; is this normal?

Yes, this is typical of our deuterated products. Our deuterated products contain less than 1 % d0. However, the labeled compounds are not 100% of the deuterated form listed on our product insert. For example, upon analysis of 2-arachidonoyl glycerol-d8 it is expected to see masses associated with the d7, d6, d5 etc.

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4-hydroxy Nonenal Mercapturic Acid-d3 Exclusive