| Identification | Back Directory | [Name]
WS 12 | [CAS]
68489-09-8 | [Synonyms]
WS 12
Cooling agent WS12
N-(4-Methoxyphenyl)-p-menthane-3-carboxamide
N- (4- methoxy phenyl) - menthol -3- carboxylase
N-(4-Methoxyphenyl)-p-menthane-3-carboxamide(WS-12)
(2S,5R)-2-Isopropyl-N-(4-methoxyphenyl)-5-methylcyclohexanecarboximide
Cyclohexanecarboxamide, N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)-
(1R,2S,5R)-2-Isopropyl-N-(4-methoxyphenyl)-5-methylcyclohexane-1-carboxamide
(1R*,2S*)-N-(4-Methoxyphenyl)-5-methyl-2-(1-methylethyl)cyclohexanecarboxamide
(1R,2S,5R)-N-(4-METHOXYPHENYL)-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANECARBOXAMIDE
CyclohexanecarboxaMide, N-(4-Methoxyphenyl)-5-Methyl-2-(1-Methylethyl)-, (1R,2S,5R)- | [EINECS(EC#)]
256-974-4 | [Molecular Formula]
C18H27NO2 | [MDL Number]
MFCD11100191 | [MOL File]
68489-09-8.mol | [Molecular Weight]
289.416 |
| Chemical Properties | Back Directory | [Boiling point ]
447.8±28.0 °C(Predicted) | [density ]
1.029±0.06 g/cm3(Predicted) | [vapor pressure ]
0-0Pa at 20-50℃ | [FEMA ]
4681 | (1R,2S,5R)-N-(4-METHOXYPHENYL)-5-METHYL-2-(1-METHYLETHYL)CYCLOHEXANECARBOXAMIDE | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: >20mg/mL | [form ]
White to off-white powder. | [pka]
14.18±0.70(Predicted) | [color ]
white to off-white | [Odor]
at 100.00 %. cool minty | [Odor Type]
minty | [JECFA Number]
2079 | [InChI]
1S/C18H27NO2/c1-12(2)16-10-5-13(3)11-17(16)18(20)19-14-6-8-15(21-4)9-7-14/h6-9,12-13,16-17H,5,10-11H2,1-4H3,(H,19,20)/t13-,16,17/m1/s1 | [InChIKey]
HNSGVPAAXJJOPQ-XOKHGSTOSA-N | [SMILES]
COc1ccc(NC(=O)C2C[C@H](C)CC[C@H]2C(C)C)cc1 | [LogP]
3.95 at 22℃ and pH7.7 | [CAS DataBase Reference]
68489-09-8 |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS09 | [Signal word ]
Warning | [Hazard statements ]
H410 | [Precautionary statements ]
P273-P391-P501 | [Hazard Codes ]
N | [Risk Statements ]
50 | [Safety Statements ]
53-61 | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
WGK 3 | [REACH Registrations]
Active | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1 |
| Hazard Information | Back Directory | [Description]
WS-12 is an agonist of transient receptor potential melastatin 8 (TRPM8). It induces currents in Xenopus oocytes expressing mouse TRPM8 (EC50 = 12 μM) and is selective for TRPM8 over transient receptor potential vanilloid 1-4 (TRPV1-4) and transient receptor potential ankyrin 1 (TRPA1) at 1 mM. WS-12 (6 nmol, i.c.v.) reduces nocifensive behavior induced by capsaicin in wild-type, but not Trpm8-/-, mice. It induces analgesia in the hot plate test, an effect that can be reversed by the opioid receptor antagonist naloxone, in mice. | [Chemical Properties]
WS 12 is a odorless white crystalline solid,mp 178 °C, displaying
a strong initial cooling effect and a long-lastingness. It is used particularly is oral
care flavors. | [Uses]
Cooling agent. High-affinity TRPM8 (cold menthol receptor 1; CMR1) agonist. Has an EC50 value ~2'000 times lower than that of (-)-menthol . | [Trade name]
Winsense WS-12 (Renessenz) | [Biological Activity]
Potent TRPM8 agonist that acts as a cooling agent (EC 50 = 193 nM). | [Biochem/physiol Actions]
WS-12 is a menthol derivative, that shows a specific binding affinity towards TRPM8 (transient receptor potential cation channel subfamily M member 8) receptor. TRPM8 is associated with prostate cancer and thus, WS-12 might be useful in reducing the progression of cancer. | [storage]
Store at -20°C | [References]
[1] SHERKHELI MA. Menthol derivative WS-12 selectively activates transient receptor potential melastatin-8 (TRPM8) ion channels.[J]. Pakistan journal of pharmaceutical sciences, 2008, 21 4: 370-378.
[2] BOYI LIU . TRPM8 is the principal mediator of menthol-induced analgesia of acute and inflammatory pain[J]. PAIN?, 2013, 154 10: Pages 2169-2177. DOI: 10.1016/j.pain.2013.06.043 |
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Sigma-Aldrich
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021-61415566 800-8193336 |
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https://www.sigmaaldrich.cn |
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