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Cayman is a manufacturer, supplier, and vendor of biochemical reagents, assay kits, forensic chemistry standards, antibodies, and proteins for scientific research. Analytical testing services and custom synthesis are also available.

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

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(±)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
Bulk Contact
Cart Total $0.00

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Pricing updated 2015-02-28. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

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

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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.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

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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