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| Product Name: | ICILIN | | Synonyms: | ICILIN;3,6-DIHYDRO-1-(2-HYDROXYPHENYL)-4-(3-NITROPHENYL)-2(1H)-PYRIMIDINONE;AG-3-5;3,4-DIHYDRO-3-(2-HYDROXYPHENYL)-6-(3-NITROPHENYL)-(1H)-PYRIMIDIN-2-ONE;1-(2-HYDROXYPHENYL)-4-(3-NITROPHENYL)-1,2,3,6-TETRAHYDROPYRIMIDIN-2-ONE;1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one;3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-2(1h)-pyrimidinon;Iciline | | CAS: | 36945-98-9 | | MF: | C16H13N3O4 | | MW: | 311.29 | | EINECS: | | Product Categories: | Vanilloid/TRPV channel;Inhibitors | | Mol File: | 36945-98-9.mol |
| ICILIN Chemical Properties |
| Boiling point | 594.8±50.0 °C(Predicted) | | density | 1.415±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | DMSO: 15 mg/mL, soluble | | form | solid | | pka | 9.94±0.35(Predicted) | | color | yellow | | Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. |
| Hazard Codes | Xn | | Risk Statements | 20/21/22 | | Safety Statements | 26-36 | | WGK Germany | 3 | | RTECS | UW7397500 |
| ICILIN Usage And Synthesis |
| Description | Icilin (36945-98-9) is an activator of cold-sensitive TRP channels with 2.5-fold greater efficacy and 200-fold greater potency than menthol (EC50?= 0.36 μM for CRM1, rat orthologue of TRPM8).1 Activator at TRPM8 (EC50?= 0.2 μM)2?and ANKTM1(TRPA1)3. Activator effects require Ca2+?and are pH dependent.2,4?Icilin induced G1?arrest in PC-3 prostate cancer cells without cell death.5 | | Uses | Icilin has been used as cooling agent in anterior ventromedial preoptic area (VMPO) neurons. | | General Description | Icilin is a synthetic cooling agent and modulates human transient receptor potential cation channel (TRPA1). Icilin inhibits transient receptor potential cation channel subfamily M member 8 (TRPM8) and modulates calcium release. Icilin also suppresses transient receptor potential vanilloid subtype 3 (TRPV3). | | Biological Activity | Cooling agent that activates the novel cold receptors TRPM8 (CMR1) and TRPA1 (ANKTM1/TRPN1), members of the TRP ion channel family. Induces currents in CMR1-expressing HEK-293 cells (EC 50 = 0.36 μ M) more potently than menthol or low temperatures. Produces "wet shakes" in vivo . | | Biochem/physiol Actions | Icilin is a potent agonist at the CMR1 cold- and menthol-sensitive receptor. | | References | 1) McKemy?et al. (2002)?Identification of a cold receptor reveals a general role for TRP channels in thermosensation; Nature,?416?52
2) Andersson?et al. (2004)?TRPM8 activation by menthol, icilin and cold is differentially modulated by intracellular pH; J .Neurosci.,?24?5364
3) Story?et al. (2003)?ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures; Cell,?112?819
4) Chuang?et al. (2004)?The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel; Neuron,?43?859
5) Kim?et al. (2011)?Icilin induces G1?arrest through activating JNK and p38 kinase in a TRPM8-independent manner; Biochem. Biophys. Res .Commun.,?406?30 |
| ICILIN Preparation Products And Raw materials |
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