专利号:US-2018312463-A1 优先权日:2015-10-22 标题:Synthesis of Cyclohexane Carboxamide Derivatives Useful as Sensates in Consumer Products 发明人:YELM KENNETH EDWARD; WOS JOHN AUGUST; BUNKE GREGORY MARK; FREDERICK HEATH; HAUGHT JOHN CHRISTIAN; HOKE STEVEN HAMILTON; SREEKRISHNA KOTI TATACHAR; LIN YAKANG 权利人:PROCTER & GAMBLE 摘要:Synthesis methods to produce a series of carboxamides built off of an (S)-2-amino acid backbone or an (R)-2-amino acid backbone, depending upon the desired diastereomer of the end product.
专利号:US-2019276389-A1 优先权日:2015-12-18 标题:Synthesis of aryl cyclohexane ester derivatives useful as sensates in consumer products 发明人:WOS JOHN AUGUST; YELM KENNETH EDWARD; BUNKE GREGORY MARK; FREDERICK HEATH ALAN; REILLY MICHAEL; HAUGHT JOHN CHRISTIAN; SREEKRISHNA KOTI TATACHAR; LIN YAKANG 权利人:PROCTER & GAMBLE 摘要:Personal care compositions, such as oral care and skin care compositions containing a flavor/perfume system comprising one or more coolants. The pleasant cool sensation provided by a coolant is enhanced in terms of quicker onset, greater intensity, impact or longer duration, which improves appeal and acceptability of the compositions to consumers.
专利号:US-8754259-B2 优先权日:2008-08-15 标 题 :Synthesis of cyclohexane derivatives useful as sensates in consumer products 发明人:YELM KENNETH EDWARD; BUNKE GREGORY MARK; HAUGHT JOHN CHRISTIAN 权利人:PROCTER & GAMBLE; PROCTER & GAMBLE 摘要:The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.
专利号:WO-2017070418-A1 优先权日:2015-10-22 标 题:Synthesis of cyclohexane carboxamide derivatives useful as sensates in consumer products
专利号:CA-2731967-A1 优先权日:2008-08-15 标 题:Synthesis of cyclohexane derivatives useful as sensates in consumer products
专利号:EP-3365324-A1 优先权日:2015-10-22 标题:Synthesis of cyclohexane carboxamide derivatives useful as sensates in consumer products
参考文献:10.1186/s12302-025-01198-3 摘要:Wang D, Yi R, Wang R, Shao K, Chen C, Mao L, Liu X, Luo T, Wang X, Wang Y. Multi-omics analysis reveals the synergistic and intergenerational toxicity of Cr(VI) and chlorfenapyr on zebrafish: disruption of gut-liver axis and mitochondrial impairment. Environ Sci Eur. 2025 Sep 26;37(1). doi: 10.1186/s12302-025-01198-3.