Item № 10004224
CAS № 478931-82-7
Purity ≥98%
25 µg $39.00 $0.00
50 µg $74.00 $0.00
100 µg $140.00 $0.00
500 µg $624.00 $0.00

Pricing updated 2016-05-06. Prices are subject to change without notice.

Bulk Inquiry Form


Enter number, size, and select unit. Example: 2 x 500 mg

Please indicate any analytical testing requirements, special handling, packaging, or delivery requirements.

  • 12,13-epoxy-9-keto-10(trans)-Octadecenoic Acid

During oxidative stress, the abundant unsaturated fatty acid linoleic acid undergoes lipid peroxidation to produce α,β-unsaturated epoxy-keto-octadecenoic acids (EKODEs). Nonenzymatic autooxidation of linoleic acid generates six major EKODE isomers, which differ from one another in the positioning and the orientation of the epoxy group relative to the keto moiety. trans-EKODE-(E)-Ib is a biologically active peroxidation product of linoleic acid that is characterized, structurally, by having a trans carbon-carbon double bond between the 9-keto and 12,13-epoxy groups. It activates an antioxidant response element (ARE) in neuronal cells and induces the expression of ARE-regulated cytoprotective genes like NQO1.1 This EKODE also stimulates the synthesis of aldosterone and corticosterone in adrenal cells when supplied at 1-5 μM.2,3 This effect appears to be mediated by a rise in intracellular calcium.4

Download Product Insert Download Safety Data Sheet (SDS) Find Batch-Specific Documents

Related Products
View Related Product Categories
Technical Information
Formal Name 9-oxo-11-(3-pentyl-2-oxiranyl)-10E-undecenoic acid
CAS Number 478931-82-7
  • 12,13-epoxy-9-keto-10(trans)-Octadecenoic Acid
Molecular Formula C18H30O4
Formula Weight 310.2
Purity ≥98%
Formulation A solution in ethanol
InChI Code 1S/C18H30O4/c1-2-3-7-11-16-17(22-16)14-13-15(19)10-8-5-4-6-9-12-18(20)21/h13-14,16-17H,2-12H2,1H3,(H,20,21)/b14-13+

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability As supplied, 1 year from the QC date provided on the Certificate of Analysis, when stored properly
Product Downloads & Resources
Product Downloads

Download Product Insert

Download Safety Data Sheet (SDS)

Download free InChI Key generation software

Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

Get Batch-Specific Data and Documents by Batch Number

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, and GC-MS data.

Please enter your batch number(s) to access inserts
QC Sheets
Please enter your batch number(s) to access QC sheets
Certificates of Analysis
Please enter your batch number(s) to access Certificates of Analysis
GC-MS Data
Please enter your batch number(s) to access GC-MS data
References & Background Reading
Product Description References

1. Wang, R., Kern, J.T., Goodfriend, T.L., et al. Activation of the antioxidant response element by specific oxidized metabolites of linoleic acid. Prostaglandins Leukot Essent Fatty Acids 81 53-59 (2009).

2. Goodfriend, T.L., Ball, D.L., Raff, H., et al. Oxidized products of linoleic acid stimulate adrenal steroidogenesis. Endocr Res 28(4) 325-330 (2002).

3. Goodfriend, T.L., Ball, D.L., Egan, B.M., et al. Epoxy-keto derivative of linoleic acid stimulates aldosterone secretion. Hypertension 43[part 2] 358-363 (2004).

4. Payet, M.D., Goodfriend, T.L., Bilodeau, L., et al. An oxidized metabolite of linoleic acid increases intracellular calcium in rat adrenal glomerulosa cells. Am J Physiol Endocrinol Metab 291 E1160-E1167 (2006).

Technical Support
Contact Us
  • To streamline the process attach the appropriate questionnaire to your inquiry.

  • Toll Free Phone (USA and Canada Only): (888) 526-5351
  • Direct Phone: (734) 975-3888
Contract Research Services

We offer you the deep and diverse knowledge of more than 100 in-house scientists and the expertise that comes from more than three decades of designing and developing the tools to advance biomedical research.

Cayman is know as a partner to scientists worldwide, responding to your needs with services in:

Cayman Chemical

1180 East Ellsworth Road

Ann Arbor, Michigan 48108 USA