(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of aqueous glyoxalic acid (200 g; 50% w/v), L-menthol (632.4 g) and concentrated sulfuric acid (3.5 g) in cyclohexane (600 mL) was refluxed at 80° C. to 85° C. for 3 to 4 hours. Water (115 mL) was removed by azeotropic distillation using a Dean Stark trap. The resulting solution was allowed to cool to room temperature and diluted with de-ionized water (500 mL). The organic layer was separated and diluted with de-ionized water (800 mL). The pH of the resultant mixture was adjusted to 5 using aqueous sodium carbonate (10%; 15 ml). The organic layer was separated and washed twice with aqueous sodium bisulfite (2×70 g in 2×800 mL of de-ionized water). The pH of the organic layer was again adjusted to 5 using aqueous sodium carbonate (10%; 20 ml) and aqueous solution of formaldehyde (130 mL) was added to it in one hour at room temperature. The pH of the resultant mixture was again adjusted to 7.5 using aqueous sodium carbonate (10%; 15 ml) and stirred for about 6 hours at room temperature. The suspension obtained was filtered and washed with de-ionized water (2×200 mL) at room temperature. The wet mass obtained was suspended in de-ionized water (1000 mL) and stirred for 2 hours at 40° C. to 45° C. The resultant mixture was cooled to 20° C. to 25° C. and stirred at the same temperature for one hour. The suspension was filtered and washed with de-ionized water (200 mL) at room temperature to give menthyl glyoxalate as wet mass. was refluxed at 80° C. to 85° C. for 3 to 4 hours Water (115 mL) was removed by azeotropic distillation diluted with de-ionized water (500 mL) The organic layer was separated diluted with de-ionized water (800 mL) The organic layer was separated washed twice with aqueous sodium bisulfite (2×70 g in 2×800 mL of de-ionized water) was added to it in one hour at room temperature The suspension obtained was filtered washed with de-ionized water (2×200 mL) at room temperature The wet mass obtained stirred for 2 hours at 40° C. to 45° C stirred at the same temperature for one hour The suspension was filtered washed with de-ionized water (200 mL) at room temperature

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Each dog fasting one whole day and night (weighing about 10 kg) received atropine sulfate as a pre-anesthesia drug intravenously followed by intravenous sodium thiopental to effect the anesthesia. An intratracheal tube was inserted and fixed. A gas mixture of nitrous oxide and oxygen was introduced. Using an isoflurane vaporizer the isoflurane was introduced. The concentration of the isoflurane was increased gradually from 0.5%, whereby maintaining the anesthesia. An intratracheal tube was inserted was introduced was introduced maintaining the anesthesia

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Thereafter, the warm aqueous mixture is filtered by using 100 mesh sieve and residues from the first filtration are extracted with. 20 l of water at a temperature of 80°-100° C. for 1 hour and condensed and under the reduced. Pressure to produce about 15 l of a natural substance extract. After 76.7 g of Bezoar bovis and 63.3 g of Moschus are dried on a silicagel desiccator for 24 hours and ground into microparticle size in a grinder to form a microparticle mixture by using 140 mesh sieve to make a Bezoar bovis powder and a Moschus powder, respectively. 5 Kg of conc-glycerin, 5 Kg of sugar and 35 Kg of d-sorbitol or 35 Kg of "ASPARTAME" and 10 Kg of Mel are solved with 10 l of distilled warm water for 15 minutes to make a sweetening solution. 5 l of distilled water is added to 110.0 g of genus Gelatin and the aqueous mixture is heated to produce a Gelatin solution. And 63.3 g of Borneol, and 0.5 l of L-menthol are solved with 3.5 l of ethanol to produce a Borneol-ethanol solution. Thereafter, the warm aqueous mixture is filtered from the first filtration are extracted with condensed Pressure to produce about 15 l of a natural substance extract After 76.7 g of Bezoar bovis and 63.3 g of Moschus are dried on a silicagel desiccator for 24 hours ground into microparticle size in a grinder to form a microparticle mixture of distilled warm water for 15 minutes 5 l of distilled water is added to 110.0 g of genus Gelatin the aqueous mixture is heated to produce a Gelatin solution

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5 l of distilled water is added to 233.3 g of the genus Gelatin and the aqueous mixture is heated to produce a Gelatin solution. And 137 g of Borneol, and 0.5 l of l-menthol are solved with 3.5 l of ethanol to produce a Borneol-ethanol solution. the aqueous mixture is heated to produce a Gelatin solution

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 7 l of distilled water is added to 350 g of the genus Gelatin and the aqueous mixture is heated to produce a Gelatin solution. And 205 g of Borneol, 50 g of p-oxybenzoic methylester, 30 g of p-oxybenzoic propylester, and 0.5 l of l-menthol are solved with 3.5 l of ethanol to produce a Borneol-ethanol solution. the aqueous mixture is heated to produce a Gelatin solution

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 7 of distilled water is added to 330 g of the genus Gelatin and the aqueous mixture is heated to produce a Gelatin solution. And 190 g of Borneol, 50 g of p-oxybenzoic methylester, 30 g of p-oxybenzoic propylester, and 0.5 l of l-menthol are solved with 3.5 l of ethanol to produce a Borneol-ethanol solution. the aqueous mixture is heated to produce a Gelatin solution

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 0.1% 1-menthol solution is prepared by mixing 30 g of ethyl alcohol, 1.2 g of a surface active agent, 145.65 g of distilled water and 0.15 g of menthol. The mixed solution is diluted twice with distilled water to prepare a control solution. A separate test solution is prepared by dissolving 0.15 g of menthyl glucoside in 100 g of distilled water. to prepare a control solution A separate test solution is prepared

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 0.1% 1-menthol solution is prepared by mixing 30 g of ethyl alcohol, 1.2 g of a surface active agent, 145.65 g of distilled water and 0.15 g of menthol. The mixed solution is diluted twice with distilled water to prepare a control solution. A separate test solution is prepared by dissolving 0.15 g of menthyl glucoside in 100 g of distilled water. to prepare a control solution A separate test solution is prepared

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1 g of a sodium hydride suspension (50% strength) in paraffin oil was added at a temperature of 0° C. to a solution of 30 g of L-menthol in 300 ml of dichloromethane. A solution of 12.5 ml acrylonitrile in 50 ml dichloromethane was slowly added dropwise, and the reaction mixture was then stirred at room temperature for a further 5 hours. The reaction mixture was worked up by cautiously adding 10 ml of glacial acetic acid, followed by 200 ml of water, and then extracting the mixture with dichloromethane. The dichloromethane extract was dried over sodium sulfate, filtered and concentrated. After chromatographic purification of the residue on silica gel using n-hexane/dichloromethane as the eluent, 25.03 g of crude 2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)propionitrile were obtained and used for the next reaction step without further purification. extracting the mixture with dichloromethane The dichloromethane extract was dried over sodium sulfate filtered concentrated After chromatographic purification of the residue on silica gel

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1 g of a sodium hydride suspension (50% strength) in paraffin oil was added at a temperature of 0° C. to a solution of 30 g of L-menthol in 300 ml of dichloromethane. A solution of 12.5 ml acrylonitrile in 50 ml dichloromethane was slowly added dropwise, and the reaction mixture was then stirred at room temperature for a further 5 hours. The reaction mixture was worked up by cautiously adding 10 ml of glacial acetic acid, followed by 200 ml of water, and then extracting the mixture with dichloromethane. The dichloromethane extract was dried over sodium sulfate, filtered and concentrated. After chromatographic purification of the residue on silica gel using n-hexane/dichloromethane as the eluent, 25.03 g of crude 2-((1R,3R,4S)-1-methyl-4-isopropylcyclohex-3-yloxy)propionitrile were obtained and used for the next reaction step without further purification. extracting the mixture with dichloromethane The dichloromethane extract was dried over sodium sulfate filtered concentrated After chromatographic purification of the residue on silica gel

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Two-hundred and sixteen parts of L-menthol and 43.2 parts of eucalyptus oil were dissolved in 100 parts of ethyl alcohol, and the resultant solution was added with 800 parts of an anhydrous maltose obtained by the method in Example for Reference 3. The resultant was granulated by spraying thereto 105 parts of a peppermint liquor, moisture content of about 50%, with stirring.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mouthwash (oral rinse) formulation of the present invention was prepared according to the following method. 7.5 g of Lecithin E-80, 625 mg of chlorhexidine diacetate, 525 mg of Tween-80, 250 mg of D,L-Menthol and 30 mg of alpha-tocopherol acid succinate were dissolved in mixture of 20 ml of absolute ethyl alcohol and 10 ml of propylene glycol. The resultant stock solution was mixed with vigorous stirring with 480 ml of distilled water and 10 g of pure glycerol was added as sweetener to obtain a suspension. The suspension was then filtered sequentially first through a 0.45 micron and then through a 0.22 micron PTFE membrane. A mouthwash (oral rinse) formulation of the present invention was prepared The resultant stock solution was mixed was added as sweetener to obtain a suspension The suspension was then filtered sequentially first through a 0.45 micron