(±)13-HpODE

Cayman Chemical Item Number 10704

(CAS 23017-93-8)

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Description

(±)13-HpODE is a racemic mixture of hydroperoxides derived non-enzymatically from linoleic acid through the action of reactive oxygen species. Lipid hydroperoxides, including 13-HpODE, have limited direct biological actions, such as the activation of lipoxygenases.1 Normally, (±)13-HpODE is rapidly reduced to (±)13-HODE, a compound which exhibits many biological activities.2 Importantly, 13-HpODE can also be metabolized to unsaturated aldehydes that can, in turn, covalently bind to DNA, amino acids, and proteins.3,4,5

1. Jones, G.D., Russell, L., Darley-Usmar, V.M., et al. Role of lipid hydroperoxides in the activation of 15-lipoxygenase. Biochemistry 35 7197-7203 (1996).

2. Kühn, H. Biosynthesis, metabolization and biological importance of the primary 15-lipoxygenase metabolites 15-hydro(pero)xy-5Z,8Z,11Z,13E-eicosatetraenoic acid and 13-hydro(pero)xy-9Z,11E-octadecadienoic acid. Prog Lipid Res 35 203-226 (1996).

3. Williams, M.V., Wishnok, J.S., and Tannenbaum, S.R. Covalent adducts arising from the decomposition products lipid hydroperoxides in the presence of cytochrome C. Chem Res Toxicol 20(5) 767-75 (2007).

4. Iwahashi, H., Nishizaki, K., and Takagi, I. Cytochrome c catalyzes the formation of pentyl radical and octanoic acid radical from linoleic acid hydroperoxide. Biochem J 361 57-66 (2002).

5. Kawai, Y., Kato, Y., Fujii, H., et al. Immunochemical detection of a novel lysine adduct using an antibody to linoleic acid hydroperoxide-modifies protein. J Lipid Res 44 1124-1131 (2003).

Formal Name (±)13-​hydroperoxy-​9Z,​11E-​octadecadienoic acid
CAS Number 23017-93-8
Molecular Formula C18H32O4
Formula Weight 312.4
Formulation A solution in ethanol
Purity ≥98%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCCC(OO)​/C=C/C=C\CCCCCCCC(O)​=O
InCHI Code
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​1S/C18H32O4/c1-2-3-11-14-17(22-21)​15-12-9-7-5-4-6-8-10-13-16-18(19)​20/h7,9,12,15,17,21H,2-6,8,10-11,13-14,16H2,1H3,(H,19,20)​/b9-7-,15-12+
InCHI Key
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JDSRHVWSAMTSSN-BSZOFBHHSA-N

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Size Price Quantity Subtotal
50 µg $55.00 $0.00
100 µg $105.00 $0.00
500 µg $440.00 $0.00
1 mg $770.00 $0.00
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Related Products

(±)13-HODE
13(R)-HODE
13(S)-HODE
13(S)-HpODE
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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.

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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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