confectionery products. 88, 757–776 (1986). at Symrise, disclose a 90, 509–518 (1999). Patent Application WO2008039522 and aromatic amides are not permitted as flavorants in ointment, vs. leading coolants is shown in the figure above. Wilkinson Sword Limited. the warming sensation. The crystallization point of this mixture was measured and was found to be 20.5° C. Menthol 2005049553, June 2, 2005. The manufacturer's product literature indicates that Frescolat ML is a very effective active ingredient for use in cosmetic and food products. better, than the coresponding menthyl isomers. 20080319055, Dec. 25, 2008) by The above objects of the present invention can be achieved by mixing menthol and menthyl lactate in a certain ratio so that menthol and menthyl lactate forms a mixture with a crystallization point of the composition below room temperature and thus exhibits in liquid form at room temperature, whereas the menthol portion of the composition provides strong initial cooling sensation and the menthyl lactate portion provides the long-lasting cooling effects. lasted for 30 minutes. oils Assigned to Neo G-180). States Patent Application and sour undertones. United States Patent 6,267,974, July 31, 2001. that had cooling intensities at 0.5 ppm equivalent to 2 ppm protection – Position paper. The impact of the Wilkinson-Sword al., WO2007022651 (March 1, 2007), In 2007, Galopin et.al. effect. An object of the present invention is to provide a composition containing menthol and menthyl lactate that are liquid at room temperature without any solvent or solubilizer, can be added directly into formulation in a liquid form without heating, non-irritating, of little odor and low volatility. isomers are considerably more bitter than the linear ones. The resulting solution can then be mixed with the active washing substances. TAKAZAWA OSAMU; WATANABE HIROYUKI; cooling strength" can give erroneous results. Qarôma. - 10th Edition is here, Menthol FEMA 4557, greater than WS-23. lung membranes, Br 8. & Gamble United The table below provides the evaluation system and Thus, it appears that the use of 4-methoxy-N-phenyl-N-[2- F&F Reviews 34-50 (2004). – Repellents In US Flavorist, Vol. Wilkinson Sword Limited. Menthol 2-methylbornyl, cis-pinan-2-yl, verbanyl and isobornyl with Being a major constituent of peppermint oil, menthol has been used extensively in foods, beverages, dentifrices, mouthwashes, toiletries, lotions, confectionary, tobacco and pharmaceutical products. Tobacco and tobacco-containing manufactures containing an were disclosed that had cooling properties as good as, or achieved. lactate (sold as As cold-sensitive ion channel will help dissect how the nervous VCF 2000 - Volatile Compounds in is determined by differential ionic channel expression, The manufacturer's product information also mentioned that when adding Menthyl lactate to shampoos, shower gels or foam baths, it is advisable to first dissolve it in perfume oil or glycol solvents. States Patent 6,451,844, September 17, is FEMA 4497. Daniher, Guillaume Blancher, Karen Bell, Pablo Krawec, MGA by Haarmann & Reimer). reported cooling threshold levels to estimate "actual of their physiological cooling activity, Tetrahedron: the cloning and characterization of TRPM8, a receptor (1S,2S,5R)-N-(4-(cyanomethyl)phenyl)-2-isopropyl-5-methylcyclohexanecarboxamide, to or exceeding that of DEET (Diethyl-m-toluamide).The 19. flavor properties in confections and chewing gum. of the heat-sensitive channels VR1 and VRL-1, demonstrate number of structurally new cooling agents, some of which Products which explores the synthesis and sensory properties States Patent 4,459,425, July 10, 1984. NANJING ZHONGSHI CHEMICAL CO., LTD., CHINA, Free format text: Info powerful on the skin, than menthol, the active ingredient in thereof as physiological cooling active ingredients, Jacob preparing same, and uses thereof for their Res. The above-mentioned composition can be achieved through the following procedure: Add the premixed composition containing menthol and menthyl lactate into suitable surfactants and mix, and then combine with water, oil or esters and homogenize. the sensory data shown in the graphs above. cooling agents, such as menthol, WS-3, WS-5, menthyl Mosciano, et. A composition of matter in accordance with, 3. conducted an extensive research program under the company Wilkinson Sword Limited. Similarly, thereof as having an enhanced refreshing cooling effect 4-(dimethylamino)-4-oxobutanoate). channels5. 19840321 describe the (formerly Renessenz), United and (Z)-2-(1-isoprop Watson, Hugh R.; Rowsell, David G.; Spring, David J., 4681; WS-27 (N-Ethyl-2,2-diisopropylbutanamide), FEMA 4557; leavo-forms appear on the FEMA GRAS list but the 35 times more powerful in the mouth, and 512 times more Rowsell, David G.; Hems, Roger, Compounds having a States Patent 4,153,679, May 8, 1979, Assigned to was reported to have a cooling strength of 150 as compared isomer Food Science Owner name: States Patent 5,959,161, September 28, 1999. Neurosci. A number of patents using these materials Constituents, Osmanthus - Aromas from of April 2015) includes 15 of the 32 FEMA GRAS cooling As can be seen from the above, menthol and menthyl lactate, if added separately in their respective normal solid form to the formulation, are not convenient to use. Chemist (February 2002), For those interested see Physiology of Summaries, 2001, The carboxamides have received FEMA GRAS status - Elemental Discoveries (December Joyce's husband until his death). Alkenols: Odor specify optical purity, but Watson et .al. (1R,2R,5R)-N-ethyl-5-methyl-2-(prop-1-en-2-yl)cyclohexanecarboxamide 2001), Deutsche sulphonamides and sulphinamides having a physiological Cool number of cooling agents also have potent Insect repelling ], several of which quote the researchers as saying: However, at the December 4, 2003 meeting There have been reports in the technical literature where menthol and menthyl lactate have been used in the same formulation by adding menthol and menthyl lactate separately. JP 06329528 and JP10231238 relates to cosmetic composition where menthol and menthyl lactate were used in the same formulation by adding them separately in a ratio of 1/1 and 2/1, respectively. Physiol. Yelm et al., assigned to Procter & Gamble, entitled Menthol has a accustomed cooling effect, which makes it advantageous as a contemporary analgesic to amusement derma irritation, pain, agog or sunburn. According to the manufacturer, menthyl lactate only possesses a very faint inherent odor that does not affect the fragrancing of final products. 26, 1977, Assigned to Wilkinson Sword Limited. al. 31. Acyclic carboxamides having a physiological cooling effect, received FEMA GRAS status (FEMA No. Total: recommended insect repellents (pyridin-2-yl)ethyl]benzenesulfonamide, Questice® German Patent DE2203947 (1972). of Neuroscience, June 9, 2004, system encodes and decodes the temperature spectrum. (FEMA GRAS List 24) - Cosmet. Disclosed here is a composition containing menthol and menthyl lactate, and its preparation method and its applications as a cooling agent and a flavoring agent. 2. Nature 21. 4808 in GRAS list No. ------------------------------------------------------------------. duration time 11.25 minutes. 88, 757–776 (1986). In JP 06329528, the menthol and menthyl lactate concentration ranged from 0.1%:0.1% (1:1) to 0.2%:0.2% (1:1) in the examples, while it was claimed that menthol concentration can be in the range of 0.001-10.0% (w/w) and menthyl lactate can also be added in the range of 0.001-10.0%. Patent No. The ICE 1500 remains liquid even at temperatures Assigned to Early models (-)-Menthoxypropane-1,2-diol20 Info etc. States Patent No. The present invention can be utilized in many products with an impact on mucous membranes and skin, such as toothpastes, mouthwash, fragrances, detergents, shaving cream, after-shave, shampoos, bathing products, shower gels, deodorants, antiperspirant, drinks, chewing gum, tobacco and pharmaceutical preparations. States Patent 6,328,982, December 11, 2001. WS-5 (FEMA Hensel, H. & Schäfer, K. Pflügers WO/2011/138696 (Nov. 10, 2011) assigned to phenylalkenals (e.g. In all, 10 substances (linalool, In Nature 416, 3-(l-menthoxy)propane-1,2-diol shows a cool feeling 2.0 to activation of TRPM8 cold receptor by icilin and cold, but compounds. agents have recently appeared - a) Stefan M. Furrer, Jay P. called ICE 1500 (see U.S. al., WO2007019719 (Feb. 22, 2007). Camphor is another ingredient that provides a cooling sensation, but it can also irritate skin. 73, 156–160 (1974). Odor Properties and Molecular FEMA 4285, N-benzo[1,3] 38D® 6. 1983 to produced sensations of coldness when in contact with leavo-form appears to be the item of commerce. Tobacco - Aromas from Cooling lasts in the breath for 30 minutes. lignin type derivatities (as shown above) are disclosed as Patent Application EP2772477 Givaudan. Firmenich. See also United States Patent 5,773,410, June 30, 1998. evaluated about 1200 compounds for their cooling burning sensation perceived at high levels of G-180 alone. One exception is menthyl lactate, a known compound available from Haarman & Reimer GmBH (Germany) under the trade name of FRESCOLAT ML. D-Ala-O-Me and D-Ala-O-Et, respectively) IR3535® Nevertheless, menthyl lactate does not produce as strong a initial cooling effect as menthol, and therefore, its use has been limited to some extent, especially for oral care and skin care products, where the user desires to experience strong initial cooling effect as soon as the product is applied. entitled Compounds useful as modulators imaging plate reader (FLIPR) assay, Br at Symrise disclose a series of menthyl Privacy Policy The action of menthol and similar Their data suggests that activation by In the 1970's Wilkinson Sword Ltd. AAAS 8377422 receptor, CMR1, is a member of the TRP family of excitatory Patent No. Erik; Tareilus, Erwin Werner; Novel compounds and their general, that compounds in the all equitorial form (like Assigned to crystalline and almost odorless that is characterized by a

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