WS 12 Chemical Properties

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. 

-20°C

solubility 

DMSO: >20mg/mL

pka

14.18±0.70(Predicted)

form 

White to off-white powder.

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 Information

Hazard Codes 

N

Risk Statements 

50

Safety Statements 

53-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

Hazard Classifications

Aquatic Acute 1
Aquatic Chronic 1

WS 12 Usage And Synthesis

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

WS 12 is a potent TRPM8 agonist.

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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