Peroxylinoleic acid CAS No. 7722-17-0

Product Description

Peroxylinoleic acid, also known as linoleic acid hydroperoxide (LAHp), is an early and highly reactive lipid oxidation product generated by the attack of the abundant omega-6 fatty acid linoleic acid by reactive oxygen species or enzymes such as lipoxygenases. This attack inserts a hydroperoxide group (-OOH) at carbon 9 or carbon 13 of the original diene chain, resulting in the major isomers 9-HpODE and 13-HpODE. Due to its conjugated diene structure and peroxide bond, peroxylinoleic acid is both a biomarker and a chemical hybrid of oxidative stress: it signals the onset of oxidation of membrane or food lipids, but it can also break down into harmful aldehydes such as 4-hydroxy-2-nonenal, which covalently modify proteins and DNA, thereby initiating inflammation, atherosclerosis, neurodegeneration, and food rancidity. Analytical chemists track its appearance via high-performance liquid chromatography, mass spectrometry, or the characteristic 234 nm UV absorption of its conjugated diene systems, while the food and flavor industries exploit its controlled enzymatic formation to generate bio-based monomers for “green” aroma compounds and sustainable polymers.

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Product Use & Characteristics

Synonyms: (9Z,12Z)-octadeca-9,12-dieneperoxoic acid, linoleic acid hydroperoxide
MF: C₁₈H₃₂O₃  MW: 296.4 g/mol

1. Synthesis Methods

• Chemical oxidation

  • Fenton’s system (Fe²⁺/H₂O₂) – generates 9-HPODE, 13-HPODE and isomers.

• Enzymatic oxidation

  • Lipoxygenase (LOX) – regio- and stereoselective formation of 13(S)-HPODE or 9(S)-HPODE.

• Autoxidation

  • Spontaneous peroxidation of linoleic acid in presence of O₂ and trace metals.

2. Properties & Characteristics

• Structure: conjugated diene with a hydroperoxy (-OOH) group at C-9 or C-13.

• Stability: highly unstable to heat, light, metal ions; decomposes to secondary products (e.g., 4-HNE, MDA).

• Reactivity:

  • Acts as strong oxidizer; reacts with thiols (e.g., PON1-Cys284, GSH).

  • Inhibits enzymes (e.g., paraoxonase 1) via covalent modification of active-site cysteines.

• Spectral data:

  • UV λmax ≈ 234 nm (conjugated diene).

  • HPLC-MS/MS signature: m/z 295.2 [M–H]⁻; characteristic fragments for 9- or 13-HPODE.

3. Uses

Area	Application
Industrial biotechnology	- Precursor for mid-chain hydroxy-fatty acids, epoxides, diacids and carbonyls.
Biomedical research	- Biomarker of lipid peroxidation and oxidative stress in atherosclerosis, aging, neurodegeneration.
Food chemistry	- Early indicator of rancidity in vegetable oils and lipid-rich foods.
Pharmacology	- Model hydroperoxide for testing antioxidant capacity of coumarins, polyphenols, vitamin E analogues.

4. Analytical Detection

• HPLC-UV at 234 nm (quantitative).

• HPLC-MS/MS for isomer-specific identification.

• FOX assay (ferrous oxidation-xylenol orange) – total hydroperoxide quantification.

• Immunoassay – antibody 13Ab specifically recognizes AZL-lysine adduct derived from LA-OOH-modified proteins.

5. Biological Interaction Highlights

• Inhibits PON1 via reaction with Cys284, converting LA-OOH to LA-OH.

• Shifts arachidonic acid metabolism from prostaglandin (COX pathway) to arachidonoyl-CoA (ACS pathway) under low substrate concentrations.

• Cytotoxicity toward endothelial cells (HUVEC) – attenuated by coumarins with catechol moieties (e.g., esculetin).

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