(±)9,10-DiHOME

Cayman Chemical Item Number 53400

Leukotoxin diol (CAS 263399-34-4)

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Description

Leukotoxin is the 9(10) epoxide of linoleic acid, generated by neutrophils during the oxidative burst.1,2,3 This unstable compound is rapidly degraded by epoxide hydrolases to form the diol, 9,10-DiHOME.4 Mitochondrial dysfunction, vasodilation, and apoptosis are features of leukotoxin toxicity. In renal proximal tubular cells, the diol hydrolysis products of leukotoxin, such as 9,10-DiHOME, have been directly implicated as the cytotoxic agent responsible for cell death.5

1. Hayakawa, M., Sugiyama, S., Takamura, T., et al. Neutrophils biosynthesize leukotoxin, 9,10-epoxy-12-octadecenoate. Biochem Biophys Res Commun 137 424-430 (1986).

2. Ishizaki, T., Takahashi, H., Ozawa, T., et al. Leukotoxin, 9,10-epoxy-12-octadecenoate causes pulmonary vasodilation in rats. J Am Physiol Soc 1040 L123-L128 (1995).

3. Ozawa, T., Hayakawa, M., Takamura, T., et al. Biosynthesis of leukotoxin, 9,10-epoxy-12 octadecenoate, by leukocytes in lung lavages of rat after exposure to hyperoxia. Biochem Biophys Res Commun 134 1071-1078 (1986).

4. Greene, J.F., Williamson, K.C., Newman, J.W., et al. Metabolism of monoepoxides of methyl linoleate: Bioactivation and detoxification. Arch Biochem Biophys 376 420-432 (2000).

5. Moran, J.H., Weise, R., Schnellmann, R.G., et al. Cytotoxicity of linoleic acid diols to renal proximal tubular cells. Toxicol Appl Pharmacol 146 53-59 (1997).

Synonyms
  • Leukotoxin diol
Formal Name (±)9(10)-​dihydroxy-​12Z-​octadecenoic acid
CAS Number 263399-34-4
Molecular Formula C18H34O4
Formula Weight 314.5
Formulation A solution in methyl acetate
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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O[C@@H]​(C/C=C\CCCCC)​[C@@H]​(O)​CCCCCCCC(O)​=O
InCHI Code
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​1S/C18H34O4/c1-2-3-4-5-7-10-13-16(19)​17(20)​14-11-8-6-9-12-15-18(21)​22/h7,10,16-17,19-20H,2-6,8-9,11-15H2,1H3,(H,21,22)​/b10-7-/t16-,17-/m0/s1
InCHI Key
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XEBKSQSGNGRGDW-CJWPDFJNSA-N

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(±)9,10-DiHOME is available in the following screening library:

Size Price Quantity Subtotal
25 µg $25.00 $0.00
50 µg $48.00 $0.00
100 µg $90.00 $0.00
500 µg $400.00 $0.00
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Related Products

(±)12,13-DiHOME
(±)9,10-DiHOME-d4
Linoleic Acid

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