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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

(±)12,13-DiHOME

Cayman Chemical Item Number 10009832

Isoleukotoxin diol (CAS 263399-35-5)

(±)12,13-DiHOME (CAS 263399-35-5)

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Description

(±)12,13-DiHOME is the diol resulting from the soluble epoxide hydrolase opening of (±)12,13-EpOME. The mixture of the methyl ester of this diol and the 9,10 isomer are more cytotoxic than the methyl ester epoxides in renal proximal tubular cells.1 However, in renal cortical mitochondria, the conversion of the epoxide to 12,13-DiHOME appears to be part of the detoxification pathway that prevents mitochondrial dysfunction.2 This diol and the 9,10 isomer can be glucuronidated by human liver and intestinal microsomes as well as recombinant UGT2B7 through a hydroxyl group. High levels of LA-diol glucuronides have been found in the urine of humans with peroxisomal diseases.3 A mixture of the diols stimulates breast cancer cell proliferation in vitro and disrupts reproductive function in rats at relatively low concentrations.4

1 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).

2 Moran, J.H., Nowak, G., and Grant, D.F. Analysis of the toxic effects of linoleic acid, 12,13-cis-epoxyoctadecenoic acid, and 12,13-dihydroxyoctadecenoic acid in rabbit renal cortical mitochondria. Toxicol Appl Pharmacol 172 150-161 (2001).

3 Jude, A.R., Little, J.M., Czernik, P.J., et al. Glucuronidation of linoleic acid diols by human microsomal and recombinant UDP-glucuronosyltransferases: Identification of UGT2B7 as the major isoform involved. Arch Biochem Biophys 389(2) 176-186 (2001).

4 Markaverich, B.M., Crowley, J.R., Alejandro, M.A., et al. Leukotoxin diols from ground corncob bedding disrupt estrous cyclicity in rats and stimulate MCF-7 breast cancer cell proliferation. Environ Health Perspect 113(12) 1698-1704 (2005).

Synonyms
  • Isoleukotoxin diol
Formal Name 12,​13-​dihydroxy-​9Z-​octadecenoic acid
CAS Number 263399-35-5
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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CCCCC[C@@H]​(O)​[C@@H]​(O)​C/C=C\CCCCCCCC(=O)​O

Background Reading

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).

Markaverich, B.M., Crowley, J.R., Alejandro, M.A., et al. Leukotoxin diols from ground corncob bedding disrupt estrous cyclicity in rats and stimulate MCF-7 breast cancer cell proliferation. Environ Health Perspect 113(12) 1698-1704 (2005).

Moran, J.H., Nowak, G., and Grant, D.F. Analysis of the toxic effects of linoleic acid, 12,13-cis-epoxyoctadecenoic acid, and 12,13-dihydroxyoctadecenoic acid in rabbit renal cortical mitochondria. Toxicol Appl Pharmacol 172 150-161 (2001).

Jude, A.R., Little, J.M., Czernik, P.J., et al. Glucuronidation of linoleic acid diols by human microsomal and recombinant UDP-glucuronosyltransferases: Identification of UGT2B7 as the major isoform involved. Arch Biochem Biophys 389(2) 176-186 (2001).

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(±)12,13-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 2012-02-12. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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