['3,419,548', '9', 'in', 'conjunction', 'with', 'varyiig', 'amounts', 'of', 'free', 'menthol', 'if', 'desired.', 'However,', 'we', 'have', 'found', 'that', 'desirable', 'cooling', 'effects', 'aro', 'obtained', 'when', 'the', 'content', 'of', 'the', 'O-(menthoxycar-', 'bonyt)}', 'polyhydroxy', 'compound', 'is', 'such', 'that', 'the', 'menthol', 'equivalent', 'is', 'between', '0.01', 'and', '1.0%', 'by', 'weight', 'of', 'the', 'smoking', 'tobacco', 'product.', 'In', 'practicing', 'our', 'invention,', 'we', 'have', 'found', 'that', 'any', 'convenient', 'method', 'may', 'be', 'used', 'to', 'incorporate', 'these', 'menthyl', 'compounds', 'in', 'the', 'smoking', 'tobacco', 'product.', 'Thus,', 'the', 'menthyl', 'compound', 'may', 'be', 'dissolved', 'in', 'a', 'suitalle', 'solvent', 'and', 'may', 'de', 'applied', 'to', 'the', 'cured,', 'cased', 'and', 'blended', 'tobacco', 'by', 'spraying', 'or', 'dipping.', 'Also', 'the', 'menthyl', 'compound', 'may', 'be', 'applied', 'to', 'the', 'paper', 'or', 'leaf', 'wrapper', 'by', 'spraying,', 'dipping', 'or', 'brushing', 'or', 'any', 'other', 'methad', 'in', 'general', 'use', 'in', 'the', 'industry.', 'Further', 'the', 'menthyl', 'compound', 'may', 'be', 'dissolved', 'or', 'suspended', 'in', 'all', 'or', 'a', 'pottion', 'of', 'the', 'casing', 'solution', 'and', 'applied', 'to', 'the', 'cured,', 'and', 'blended', 'tabacco', 'by', 'spraying', 'or', 'dipping.', 'Still', 'another', 'mode', 'of', 'application', 'may', 'be', 'by', 'incorporating', 'the', 'menthyl', 'compound', 'into', 'the', 'homogenized', 'ground', 'tobacco', 'components', 'prior', 'to', 'reconstituting', 'into', 'a', 'sheet.', 'Specific', 'examples', 'of', 'incorporating', 'O-(menthoxycar-', 'bony!)', 'polyhydroxy', 'compounds', 'into', 'a', 'tobacco', 'product', 'as', 'as', 'follows:', 'Example', '10', 'A', 'mixture', 'composed', 'of', 'approximately', '1.4', 'grams', 'of', 'di-', 'Q-(menthoxycarbonyl)', 'glucose', 'and', '0.3', 'gram', 'of', '1-men-', 'thol', 'was', 'dissolved', 'in', '4', 'ml.', 'of', '95%', 'ethanol.', 'The', 'solution', 'was', 'applied', 'by', 'spraying', 'to', '200', 'gms.', 'of', 'a', 'commercial', 'blend', 'of', 'cased', 'and', 'cut', 'tobacco', 'in', 'a', 'rotating', 'glass', 'drum.', 'The', 'solvent', 'was', 'evaporated', 'and', 'the', 'treated', 'tobacco', 'manufactured', 'into', 'cigarettes', 'on', 'a', 'Chico-type', 'cigarette', 'making', 'machine.', 'Example', '11', 'Approximately', '3.2', 'grams', 'of', 'tri-O-(menthoxycarbonyl)', 'glucose', 'was', 'dissolved', 'in', '6', 'ml.', 'of', '95%', 'ethanol.', 'The', 'solu-', 'tion', 'was', 'applied', 'by', 'spraying', 'to', '200', 'grams', 'of', 'a', 'commer-', 'cial', 'blend', 'of', 'cased', 'and', 'cut', 'tobacco.', 'After', 'evaporation', 'of', 'the', 'ethanol,', 'the', 'treated', 'tobacco', 'was', 'manufactured', 'into', 'cigarettes', 'on', 'a', 'Chico-type', 'cigarette', 'making', 'machine.', 'Example', '12', 'A', 'sample', 'of', 'approximately', '2.6', 'grams', 'of', 'tetra-O-(men-', 'thoxycarbonyl)', 'glucose', 'was', 'dissolved', 'in', '6', 'mi.', 'of', 'petro', 'leum', '¢ther.', 'The', 'solution', 'was', 'applied', 'by', 'spraying', 'to', '200', 'grams', 'of', 'a', 'commercial', 'blend', 'of', 'cased', 'and', 'cut', 'tobacco.', 'The', 'solvent', 'was', 'removed', 'completely', 'and', 'the', 'treated', 'tobacco', 'was', 'manufactured', 'into', 'cigarettes', 'on', 'a', 'Chico-type', '*', 'cigarette', 'making', 'machine.', 'Example', '13', 'Approximately', '2.8', 'grams', 'of', 'mono-O-(menthoxycar-', 'bony!)', 'glucose', 'was', 'dissolved', 'in', '4', 'ml.', 'of', '95%', 'ethanol.', '+', 'The', 'solution', 'was', 'then', 'applied', 'by', 'spraying', 'with', 'an', 'atomizer', 'to', '200', 'grams', 'of', '2', 'commercial', 'blend', 'of', 'cased', 'and', 'cut', 'tobacco', 'in', 'a', 'rotating', 'drum.', 'The', 'ethanol', 'was', 'allowed', 'to', 'evaporate', 'from', 'the', 'tobacco.', 'The', 'treated', 'tobacco', 'was', 'manufactured', 'into', 'cigarettes', 'on', 'a', 'Chico-type', 'cigarette', 'making', 'machine.', 'Example', '14', 'Approximately', '5', 'pounds', 'of', 'mono-O-(menthoxycar-', 'bony1)', 'glucose', 'was', 'dissolved', 'in', '26', 'pounds', 'of', 'a', 'casing', 'solution', 'containing', 'in', 'certain', 'proportions,', 'amounts', 'of', 'in-', 'vert', 'sugar,', 'corm', 'syrup', 'and', 'humectants', 'normally', 'used', 'to', 'case', 'tobaccos', 'destined', 'for', 'the', 'manvfacture', 'of', 'cigarettes.', 'The', 'solution', 'was', 'heated', 'to', '170°', 'F.', 'and', 'was', 'maintained', 'at', 'that', 'temperature', 'for', 'two', 'and', 'one-half', 'hours,', 'Subse-', 'quently', 'the', 'casing', 'solution', 'was', 'applied', 'to', '150', 'pounds', 'of', 'a', 'commercial', 'blend', 'of', 'tobacco', 'strip.', 'The', 'treated', 'tobacco.', 'strip', 'was', 'mixed', 'with', 'other', 'tobacco', 'components', 'in', 'suf-', 'ficient', 'amounts', 'to', 'give', '230', 'pounds', 'of', 'finished', 'product', 'at', 'the', 'proper', 'moisture', 'level.', 'This', 'product', 'was', 'processed', 'lo', '30', '40', '70', 'aa', '10', 'through', 'all', 'of', 'the', 'manufacturing', 'operations', 'required', 'to', 'give', 'a', 'cased', 'and', 'cut,', 'finished', 'tobacco', 'biend.', 'This', 'blend', 'was', 'then', 'manufactured', 'into', 'cigarettes,', 'fitted', 'with', 'three-', 'Piece', 'charcoal', 'filters,', 'in', 'a', 'regular', 'production,', 'high', 'speed', 'cigarette', 'making', 'machine.', 'Example', '15', 'Approximately', '44.7', 'gm.', 'of', 'mono-O-(menthozycar-', 'bonyl)', 'glucose', 'was', 'suspended', 'in', 'a', 'solution', 'of', '169.0', 'mi.', 'of', 'glycol', 'humectants', 'and', '1500', 'ml.', 'of', 'water.', 'This', 'mixture', 'was', 'added', 'to', '2240', 'gms.', 'of', 'a', 'ground', 'tobacco', 'composition', 'containing', 'in', 'certain', 'proportions', 'cellulose', 'fibers', 'and', 'a', 'water-soluble', 'binder.', 'After', 'thorough', 'mixing', 'the', 'wet', 'com-', 'position', 'was', 'manufactured', 'into', 'a', 'coherent', 'tobacco', 'sheet.', 'The', 'total', 'weight', 'of', 'sheet', 'at', 'the', 'appropriate', 'moisture', 'level', 'was', 'approximately', '2400', 'gm.', 'Menthol', 'analysis', 'of', 'the', 'finished', 'product', 'following', 'alkaline', 'hydrolysis,', 'indicated', 'that', 'the', 'theoretical', 'level', 'of', '7.9', 'mg.', 'of', 'menthol', 'per', 'gram', 'of', 'product', 'was', 'achieved.', 'Approximately', '42', 'pounds', 'of', 'product,', 'prepared', 'by', 're-', 'peating', 'the', 'above', 'procedure', 'several', 'times,', 'was', 'mixed', 'with', '150', 'pounds', 'of', 'a', 'commercial', 'blend', 'tobacco', 'strip', 'which', 'had', 'been', 'cased', 'with', '30.19', 'pounds', 'of', '2', 'special', 'casing', 'solu.', 'tion', 'containing', '3.29', 'pounds', 'of', 'mono-O-(menthoxycar-', 'bony!)', 'glucose,', 'and', '57.1', 'pounds', 'of', 'other', 'tobacco', 'com-', 'ponents,', 'After', 'appropriate', 'blending,', 'cutting,', 'and', 'drying', 'operations', 'the', 'blend', 'was', 'manufactured', 'into', 'cigarettes', 'by', 'a', 'high', 'speed', 'cigarette', 'making', 'machine.', 'To', 'the', 'cigarettes', 'were', 'subsequently', 'attached', 'three-piece', 'charcoal', 'filters.', 'Example', '16', 'Approximately', '3.1', 'pounds', 'of', 'mono-O-(menthoxycar-', 'bonyl)', 'glucose', 'was', 'dissolved', 'in', '29.1', 'pounds', 'of', 'a', 'casing', 'solution', 'containing', 'in', 'certain', 'proportions,', 'amounts', 'of', 'invert', 'sugar,', 'corn', 'syrup', 'and', 'humectants', 'normally', 'used', 'to', 'case', 'tobaccos', 'destined', 'for', 'the', 'manufacture', 'of', 'ciga-', 'rettes.', 'The', 'solution', 'was', 'heated', 'to', '170°', 'F.', 'and', 'was', 'main-', 'tained', 'at', 'that', 'temperature', 'for', 'two', 'hours.', 'Subsequently', 'the', 'casing', 'solution', 'was', 'applied', 'to', '219', 'pounds', 'of', 'a', 'com-', 'mercial', 'blend', 'of', 'tobacco', 'strip.', 'The', 'treated', 'tobacco', 'strip', 'was', 'mixed', 'with', 'other', 'tobacco', 'components', 'in', 'sufficient', 'amounts', 'to', 'give', '283', 'pounds', 'of', 'finished', 'product', 'at', 'the', 'proper', 'moisture', 'level.', 'This', 'product', 'was', 'processed', 'through', 'all', 'of', 'the', 'manufacturing', 'operations', 'required', 'to', 'give', 'a', 'cased', 'and', 'cut,', 'finished', 'tobacco', 'blend,', 'This', 'biend', 'was', 'then', 'treated', 'with', 'a', 'solution', 'containing', 'approximately', '0.55', 'pound', 'of', 'free', '1-menthol', 'and', 'smaller', 'amounts', 'of', 'other', 'flavorants.', 'The', 'treated', 'blend', 'was', 'then', 'manufactured', 'into', 'cigarettes,', 'fitted', 'with', 'three-piece', 'charcoal', 'filters,', 'in', 'a', 'cepular', 'production,', 'high', 'speed', 'cigarette', 'making', 'ma-', 'chine.', 'Example', '17', 'Approximately', '2,0', 'gm.', 'of', 'mono-O-(menthoxycarbony])', 'propane-1,2-diol', 'was', 'applied,', 'by', 'spraying', 'in', 'ethanolic', 'solution,', 'to', '200', 'gm.', 'of', 'a', 'commercial', 'blend', 'cased', 'and', 'cut', 'tobacco,', 'After', 'evaporation', 'of', 'the', 'ethanol,', 'the', 'treated', 'tobacco', 'was', 'manufactured', 'into', 'cigarettes', 'in', 'a', 'Chico-type', 'cigarette', 'making', 'machine.', 'Example', '18', 'A', 'sample', 'of', '0.640', 'gm.', 'of', 'mono-O-(menthoxycarbony!', ')', 'xylose', 'was', 'dissolved', 'in', 'enough', 'ethanol', 'to', 'give', 'a', 'final', 'volume', 'of', 'solution', 'of', '1', 'ml.', 'Aliquots', 'of', '20', 'al.', 'of', 'the', '3', 'Solution', 'were', 'injected,', 'uniformly', 'along', 'a', 'path', 'of', '$5', 'mm.', 'length,', 'in', 'commercially', 'available', 'cigarettes', 'equipped', 'with', 'charcoal', 'filters.', 'The', 'solvent', 'was', 'removed', 'from', 'each', 'ciga-', 'rette', 'by', 'a', 'gentle', 'stream', 'of', 'air,', 'Example', '19', 'A', 'sample', 'of', '0.535', 'gm.', 'of', 'mono-O-(menthoxycarbony!)', 'glycerol', 'was', 'dissoived', 'in', 'enough', 'ethanol', 'to', 'give', 'a', 'final', 'volume', 'of', 'solution', 'of', 'I', 'ml.', 'Aliquots', 'of', '20', 'sl.', 'of', 'the', 'solu-', 'tion', 'were', 'injected,', 'uniformly', 'along', 'a', 'path', 'of', '55', 'mm.', 'length,', 'in', 'commercially', 'available', 'cigarettes', 'equipped', 'with', '119297920', 'rn,']