2-(14,15-Epoxyeicosatrienoyl) Glycerol CAS: 848667-56-1
MF: C23H38O5
MW: 394.5
A TACE activator which increases DNA synthesis.

2-(14,15-Epoxyeicosatrienoyl) Glycerol (CAS 848667-56-1)

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Alternate Names: 2-14,15-EG
Application: 2-(14,15-Epoxyeicosatrienoyl) Glycerol is a TACE activator which increases DNA synthesis
CAS Number: 848667-56-1
Purity: ≥95%
Molecular Weight: 394.5
Molecular Formula: C23H38O5
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).

2-(14,15-Epoxyeicosatrienoyl) Glycerol (2-14,15-EG) is a novel CYP450 metabolite of 2-Arachidonoyl glycerol (2-AG) in the kidney. 2-14,15-EG is a potent mitogen for renal epithelial cells, increasing DNA synthesis in LLCPKcl4 cells at concentrations as low as 100 nM and doubling cell proliferation rates at 1 μM. In these cells, 2-14,15-EG activates the metalloprotease ADAM17 (TACE), which cleaves proTGF-α and releases TGF-α as a ligand that initiates the EGFR-ERK signalling pathway.


References

1. Stella, N., et al., 1997. A second endogenous cannabinoid that modulates long-term potentiation. Nature. 388(6644): 773-8. PMID: 9285589
2. Kondo, S., et al., 1998. 2-Arachidonoylglycerol, an endogenous cannabinoid receptor agonist: identification as one of the major species of monoacylglycerols in various rat tissues, and evidence for its generation through CA2+-dependent and -independent mechanisms. FEBS letters. 429(2): 152-6. PMID: 9650580
3. Sugiura, T., et al., 1999. Evidence that the cannabinoid CB1 receptor is a 2-arachidonoylglycerol receptor. Structure-activity relationship of 2-arachidonoylglycerol, ether-linked analogues, and related compounds. The Journal of biological chemistry. 274(5): 2794-801. PMID: 9915812
4. Kozak, K R., et al., . Oxidative metabolism of endocannabinoids. Prostaglandins, leukotrienes, and essential fatty acids. 66(2-3): 211-20. PMID: 12052037
5. Dinh, T P., et al., 2002. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proceedings of the National Academy of Sciences of the United States of America. 99(16): 10819-24. PMID: 12136125
6. Snider, Natasha T., et al., 2007. Anandamide metabolism by human liver and kidney microsomal cytochrome p450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides. The Journal of pharmacology and experimental therapeutics. 321(2): 590-7. PMID: 17272674
7. Chen, Jianchun., et al., 2007. Mitogenic activity and signaling mechanism of 2-(14,15- epoxyeicosatrienoyl)glycerol, a novel cytochrome p450 arachidonate metabolite. Molecular and cellular biology. 27(8): 3023-34. PMID: 17283047

Formulation :
A solution in acetonitrile
Physical State :
Liquid
Solubility :
Soluble in DMSO (~10 mg/ml), DMF (~10 mg/ml), aqueous solutions, and ethanol (~50 mg/ml).
Storage :
Store at -80° C
Boiling Point :
84° C
Refractive Index :
n20D 1.51 (Predicted)
pK Values :
pKa: 14.28 (Predicted), pKb: -3 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
53481916
MDL Number :
MFCD10567087
SMILES :
CCCCCC1C(O1)CC=CCC=CCC=CCCCC(=O)OC(CO)CO

Download SDS (MSDS)

Certificate of Analysis

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