See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

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

(±)12,13-DiHOME-d4

Cayman Chemical Item Number 10009994

Isoleukotoxin diol-d4

(±)12,13-DiHOME-d4

See more

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-d4
Formal Name (±)12,​13-​dihydroxy-​9Z-​octadecenoic-​9,​10,​12,​13-​d4 acid
Molecular Formula C18H30D4O4
Formula Weight 318.5
Formulation A solution in methyl acetate
Purity ≥99% deuterated forms (d1-d4)
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCC[C@@H]​([2H]​)​(O)​[C@@H]​([2H]​)​(O)​C\C(=C(\[2H]​)​/CCCCCCCC(=O)​O)​\[2H]​

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).

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).

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).

Show all 4 Hide all but first 3
Size Price Quantity Subtotal
25 µg $75.00 $0.00
50 µg $143.00 $0.00
100 µg $270.00 $0.00
250 µg $600.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-02-12. 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
Soluble Epoxide Hydrolase Polyclonal Antibody

Downloads

Batch-specific Information

Login to access batch-specific information

Cayman Chemical is a manufacturer, supplier and vendor of biochemical reagents, assay kits, antibodies, and proteins.

Other Resources
Management Team Company Profile Company History ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map

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

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2012 Cayman Chemical Company

Lost password?