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

14,15-Leukotriene C4

Cayman Chemical Item Number 10011360

EXC4; Eoxin C4; 14,15-LTC4 (CAS 75290-60-7)

14,15-Leukotriene C4 (CAS 75290-60-7)

See more

Description

Leukotrienes (LTs) are a group of acute inflammatory mediators derived from arachidonic acid in leukocytes. The majority of these metabolites are formed through the 5-lipoxygenase (5-LO) pathway.1 14,15-LTC4 is a member of an alternate class of LTs synthesized by a pathway involving the dual actions of 15- and 12-LOs on arachidonic acid via 15-HpETE and 14,15-LTA4 intermediates.2,3,4,5 14,15-LTC4 is classified as an eoxin, because it is formed mostly by eosinophils.4 However, mast cells and nasal polyps can synthesize 14,15-LTC4 as well. Little is known about the physiological actions of 14,15-LTC4. It has weak contractile activity on both guinea pig ileum and pulmonary parenchyma in contrast to the effects of 5-LO-derived LTs.6,7 However, in an in vitro permeability assay, 14,15-LTC4 can increase vascular permeability of human endothelial cell monolayers, with similar potency to that of 5-LO-derived LTs resulting in plasma leakage - a hallmark of inflammation.4

1 Luo, M., Lee, S., and Brock, T.G. Leukotriene synthesis by epithelial cells. Histol Histopathol 18 587-595 (2003).

2 Yokoyama, C., Shinjo, F., Yoshimoto, T., et al. Arachidonate 12-lipoxygenase purified from porcine leukocytes by immunoaffinity chromatography and its reactivity with hydroperoxyeicosatetraenoic acids. J Biol Chem 261 16714-16721 (1986).

3 Bryant, R.W., Schewe, T., Rapoport, S.M., et al. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14,15-leukotriene A4. J Biol Chem 260 3548-3555 (1985).

4 Feltenmark, S., Gautam, N., Brunnström Å, et al. Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells. Proc Natl Acad Sci USA 105(2) 680-685 (2008).

5 Sailesh, S., Kumar, Y.V.K., Prasad, M., et al. Sheep uterus dual lipoxygenase in the synthesis of 14,15-leukotrienes. Arch Biochem Biophys 315(2) 362-368 (1994).

6 Drazen, J.M., Lewis, R.A., Austen, K.F., et al. Contractile activities of structural analogs of leukotrienes C and D: Necessity of a hydrophobic region. Proc Natl Acad Sci USA 78(5) 3195-3198 (1987).

7 Sala, A., Civelli, M., Oliva, D., et al. Contractile and binding activities of structural analogues of LTC4 in the longitudinal muscle of guinea-pig ileum. Eicosanoids 3 105-110 (1990).

Synonyms
  • EXC4
  • Eoxin C4
  • 14,15-LTC4
Formal Name 15S-​hydroxy-​14R-​(S-​glutathionyl)-​5Z,​8Z,​10E,​12E-​eicosatetraenoic acid
CAS Number 75290-60-7
Molecular Formula C30H47N3O9S
Formula Weight 625.8
Formulation A solution in methanol
Purity >95%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
CCCCC[C@H]​(O)​C(\C=C\C=C/C=C/C/C=C\CCCC(=O)​O)​SCC(C(=O)​NCC(=O)​O)​[N]​1(N)​C(=O)​CCC1C(=O)​O

Background Reading

Luo, M., Lee, S., and Brock, T.G. Leukotriene synthesis by epithelial cells. Histol Histopathol 18 587-595 (2003).

Yokoyama, C., Shinjo, F., Yoshimoto, T., et al. Arachidonate 12-lipoxygenase purified from porcine leukocytes by immunoaffinity chromatography and its reactivity with hydroperoxyeicosatetraenoic acids. J Biol Chem 261 16714-16721 (1986).

Feltenmark, S., Gautam, N., Brunnström Å, et al. Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells. Proc Natl Acad Sci USA 105(2) 680-685 (2008).

Drazen, J.M., Lewis, R.A., Austen, K.F., et al. Contractile activities of structural analogs of leukotrienes C and D: Necessity of a hydrophobic region. Proc Natl Acad Sci USA 78(5) 3195-3198 (1987).

Sala, A., Civelli, M., Oliva, D., et al. Contractile and binding activities of structural analogues of LTC4 in the longitudinal muscle of guinea-pig ileum. Eicosanoids 3 105-110 (1990).

Sailesh, S., Kumar, Y.V.K., Prasad, M., et al. Sheep uterus dual lipoxygenase in the synthesis of 14,15-leukotrienes. Arch Biochem Biophys 315(2) 362-368 (1994).

Bryant, R.W., Schewe, T., Rapoport, S.M., et al. Leukotriene formation by a purified reticulocyte lipoxygenase enzyme. Conversion of arachidonic acid and 15-hydroperoxyeicosatetraenoic acid to 14,15-leukotriene A4. J Biol Chem 260 3548-3555 (1985).

Show all 7 Hide all but first 3
Size Price Quantity Subtotal
25 µg $97.00 $0.00
50 µg $184.00 $0.00
100 µg $349.00 $0.00
250 µg $776.00 $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

14,15-Leukotriene C4 EIA Kit
Leukotriene C4

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?