7-[(1S,2R,3R,4R)-3-[(1E,3R)-3-HYDROXY-4-(4-IODOPHENOXY)-1-BUTENYL]-7-OXABICYCLO[2.2.1]HEPT-2-YL]-5Z-HEPTENOIC ACID
7-[(1S,2R,3R,4R)-3-[(1E,3R)-3-HYDROXY-4-(4-IODOPHENOXY)-1-BUTENYL]-7-OXABICYCLO[2.2.1]HEPT-2-YL]-5Z-HEPTENOIC ACID Basic information
- Product Name:
- 7-[(1S,2R,3R,4R)-3-[(1E,3R)-3-HYDROXY-4-(4-IODOPHENOXY)-1-BUTENYL]-7-OXABICYCLO[2.2.1]HEPT-2-YL]-5Z-HEPTENOIC ACID
- Synonyms:
-
- 7-[(1S,2R,3R,4R)-3-[(1E,3R)-3-HYDROXY-4-(4-IODOPHENOXY)-1-BUTENYL]-7-OXABICYCLO[2.2.1]HEPT-2-YL]-5Z-HEPTENOIC ACID
- I-BOP
- (5Z)-7-[(1S,4R)-3β-[(1E,3R)-3-Hydroxy-4-(p-iodophenoxy)-1-butenyl]-7-oxabicyclo[2.2.1]heptane-2α-yl]-5-heptenoic acid
- (5Z)-7-[(1S,2R,3R,4R)-3-[(1E,3R)-3-Hydroxy-4-(4-iodophenoxy)-1-buten-1-yl]-7-oxabicyclo[2.2.1]hept-2-yl]-5-heptenoic acid
- UYFMSCHBODMWON-JCPFAPSOSA-N
- I-BOP >=95% (HPLC)
- 5-Heptenoic acid, 7-[(1S,2R,3R,4R)-3-[(1E,3R)-3-hydroxy-4-(4-iodophenoxy)-1-buten-1-yl]-7-oxabicyclo[2.2.1]hept-2-yl]-, (5Z)-
- CAS:
- 128719-90-4
- MF:
- C23H29IO5
- MW:
- 512.38
- EINECS:
- 200-578-6
- Mol File:
- 128719-90-4.mol
7-[(1S,2R,3R,4R)-3-[(1E,3R)-3-HYDROXY-4-(4-IODOPHENOXY)-1-BUTENYL]-7-OXABICYCLO[2.2.1]HEPT-2-YL]-5Z-HEPTENOIC ACID Chemical Properties
- Boiling point:
- 634.5±55.0 °C(Predicted)
- Density
- 1.483±0.06 g/cm3(Predicted)
- Flash point:
- 14℃
- storage temp.
- -20°C
- solubility
- DMF: >50 mg/ml (from Pinane TXA2); DMSO: >25 mg/ml (from Pinane TXA2); Ethanol: >100 mg/ml (from Pinane TXA2); PBS (pH 7.2): 3 mg/ml
- pka
- 4.76±0.10(Predicted)
- form
- solution
- color
- colorless to faint yellow
7-[(1S,2R,3R,4R)-3-[(1E,3R)-3-HYDROXY-4-(4-IODOPHENOXY)-1-BUTENYL]-7-OXABICYCLO[2.2.1]HEPT-2-YL]-5Z-HEPTENOIC ACID Usage And Synthesis
Uses
I-BOP is an agonist for thromboxane A2 receptor (TP) with a KD of 0.61 nM. I-BOP promotes proliferation through activation of PI3K pathway in vascular smooth muscle[1]. I-BOP dose-dependently biphasicly affects the excitatory postsynaptic potential (e.p.s.p.) in hippocampal neurons[2].
Biochem/physiol Actions
I-BOP is a potent thromboxane (TP) receptor agonist. I-BOP induces human platelet aggregation with an EC50 value of 0.34 nM.
References
[1] Morinelli TA, et al., Tyrosine phosphorylation of phosphatidylinositol 3-kinase and of the thromboxane A2 (TXA2) receptor by the TXA2 mimetic I-BOP in A7r5 cells. Biochem Pharmacol. 1997 Jun 15;53(12):1823-32. DOI:10.1016/s0006-2952(97)00005-1
[2] Hsu KS, et al., Thromboxane A2 agonist modulation of excitatory synaptic transmission in the rat hippocampal slice. Br J Pharmacol. 1996 Aug;118(8):2220-7. DOI:10.1111/j.1476-5381.1996.tb15666.x
7-[(1S,2R,3R,4R)-3-[(1E,3R)-3-HYDROXY-4-(4-IODOPHENOXY)-1-BUTENYL]-7-OXABICYCLO[2.2.1]HEPT-2-YL]-5Z-HEPTENOIC ACIDSupplier
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