Cooler 5(WS-5) CAS#: 68489-14-5; ChemWhat Code: 970683
Identification
| Product Name | Cooler 5(WS-5) |
| IUPAC Name | ethyl 2-[[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexanecarbonyl]amino]acetate |
| Molecular Structure |  |
| CAS Registry Number | 68489-14-5 |
| EINECS Number | 254-573-9 |
| MDL Number | MFCD19705285 |
| Beilstein Registry Number | No data available |
| Synonyms | WS-5, [((1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbonyl)amino]acetic acid ethyl ester, ethyl ((1R,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carbonyl)glycinate, ethyl 2-((1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamido)acetate, WS5, N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine ethyl ester, Nα-(L-menthanecarbonyl)glycine ethyl ester |
| Molecular Formula | C15H27NO3 |
| Molecular Weight | 269.380 |
| InChI | InChI=1S/C15H27NO3/c1-5-19-14(17)9-16-15(18)13-8-11(4)6-7-12(13)10(2)3/h10-13H,5-9H2,1-4H3,(H,16,18)/t11-,12+,13-/m1/s1 |
| InChI Key | GWRCTWAPTXBPHW-FRRDWIJNSA-N |
| Canonical SMILES | CCOC(=O)CNC(=O)[C@@H]1C[C@@H](CC[C@H]1C(C)C)C |
| Patent Information | ||
| Patent ID | Title | Publication Date |
| EP2450337 | Process for making neo-enriched p-menthane compounds | 2012 |
| US2012/116113 | PROCESS FOR MAKING NEO-ENRICHED p-MENTHANE COMPOUNDS | 2012 |
| US2011/82204 | N-alkylcarbonyl-amino acid ester and N-alkylcarbonyl-amino lactone compounds and their use | 2011 |
| US2005/265930 | Physiological cooling compositions | 2005 |
Physical Data
| Appearance | Powder |
| Solubility | No data available |
| Flash Point | No data available |
| Refractive index | No data available |
| Sensitivity | No data available |
| Melting Point, °C | Solvent (Melting Point) |
| 80.5 – 81.4 | |
| 80 – 82 | |
| 80.4 – 80.6 | n-heptane |
| 80.9 – 81 | ethyl acetate |
| 80.9 – 81.1 | n-heptane |
| 79 – 80 |
| Density, g·cm-3 | Type (Density) |
| 1.098 | crystallographic |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Coupling Nuclei | Solvents (NMR Spectroscopy) | Frequency (NMR Spectroscopy), MHz |
| Chemical shifts | 1H | 1H | chloroform-d1 | 400 |
| Chemical shifts, Spectrum | 1H | chloroform-d1 | 500 | |
| HSQC (Heteronuclear Single Quantum Coherence) | 1H,13C | chloroform-d1 | ||
| HMBC (Heteronuclear Multiple Bond Coherence) | 1H,13C | chloroform-d1 | 101 | |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | 100 | |
| Chemical shifts | 13C |
| Description (Mass Spectrometry) |
| high resolution mass spectrometry (HRMS), electrospray ionisation (ESI), spectrum |
Route of Synthesis (ROS)
| Conditions | Yield |
| With sodium carbonate In n-heptane; water at 20 – 55℃; for 4.5h; Experimental Procedure The heptane solution of WS-1 acid chlorides (60 g, from Example 9) is added at 20-21 °C over 90 min. to a stirred solution of glycine ethyl ester hydrochloride (35.7 g, 0.256 mol) and sodium carbonate (24.7 g) in water (180 mL). The mixture is stirred for 3 h. Heptane (140 mL) is added, and the mixture is heated to 55°C and transferred at this temperature to a separatory funnel. The aqueous layer is drained. The organic layer is washed with hydrochloric acid (95 g of 2% aq. HCl), and washed with water (2 x 190 mL), maintaining the 55°C temperature. The organic layer is refluxed in an apparatus equipped with a Dean-Stark trap to remove residual moisture. The product is transferred into a crystallizer, where it is cooled to ambient temperature. The crystalline mixture of WS-5 isomers is separated by filtration and dried on the filter to give a 98.7% pure isomeric mixture (28.0 g) with a neo:normal ratio ∼2.6. The mother liquor is rotary evaporated to give additional WS-5 isomeric mixture (5.7 g), total purity 97.5%, neo:normal ratio ∼ 0.8. Combining these two crops and taking into account purities gives a total of 32.9 g of an isomeric WS-5 mixture with a neo: normal ratio – 2.14. | |
| With sodium carbonate In n-heptane; water at 20 – 55℃; for 4.5h; Experimental Procedure The heptane solution of WS-1 acid chlorides (60 g, from Example 9) is added at 20-21° C. over 90 min, to a stirred solution of glycine ethyl ester hydrochloride (35.7 g, 0.256 mol) and sodium carbonate (24.7 g) in water (180 mL). The mixture is stirred for 3 h. Heptane (140 mL) is added, and the mixture is heated to 55° C. and transferred at this temperature to a separatory funnel. The aqueous layer is drained. The organic layer is washed with hydrochloric acid (95 g of 2% aq. HCl), and washed with water (2×190 mL), maintaining the 55° C. temperature. The organic layer is refluxed in an apparatus equipped with a Dean-Stark trap to remove residual moisture. The product is transferred into a crystallizer, where it is cooled to ambient temperature. The crystalline mixture of WS-5 isomers is separated by filtration and dried on the filter to give a 98.7% pure isomeric mixture (28.0 g) with a neo:normal ratio 2.6. The mother liquor is rotary evaporated to give additional WS-5 isomeric mixture (5.7 g), total purity 97.5%, neo:normal ratio 0.8. Combining these two crops and taking into account purities gives a total of 32.9 g of an isomeric WS-5 mixture with a neo:normal ratio 2.14. |
Safety and Hazards
| Pictogram(s) |   |
| Signal | Warning |
| GHS Hazard Statements | H319 (87.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H411 (12.2%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P264, P273, P280, P305+P351+P338, P337+P313, P391, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | Not dangerous goods |
| Under the room temperature and away from light | |
| HS Code | No data avaolable |
| Storage | Under the room temperature and away from light |
| Shelf Life | 2 years |
| Market Price | USD |
| Use Pattern |
| Cooler 5(WS-5) CAS#: 68489-14-5 main component of the physiological cooling compositions |
| Cooler 5(WS-5) CAS#: 68489-14-5 physiological cooling agent |
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Approved Manufacturers | |
| Warshel Chemical Ltd | http://www.warshel.com/ |
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