CN101184470A - 清凉化合物 - Google Patents

清凉化合物 Download PDF

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CN101184470A
CN101184470A CNA2006800185961A CN200680018596A CN101184470A CN 101184470 A CN101184470 A CN 101184470A CN A2006800185961 A CNA2006800185961 A CN A2006800185961A CN 200680018596 A CN200680018596 A CN 200680018596A CN 101184470 A CN101184470 A CN 101184470A
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K·A·贝尔
S·M·富勒
C·加洛潘
P·V·克拉韦克
J·P·斯莱克
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Givaudan SA
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Abstract

提供皮肤或粘膜清凉效果的方法，该方法包括在其上施加至少一种式I的化合物：(a)其中B选自H、CH3、C2H5、OCH3、OC2H5和OH；和(b)其中A是式－CO－D的一部分，其中D选自下述部分：(i)－NR1R2，其中R1和R2独立地选自H和C1－C8直链或支链的脂族烷氧基烷基、羟烷基，芳脂族和环烷基；或R1和R2与它们连接到其上的氮原子一起形成一部分任选取代的5或6元杂环；(ii)－NHCH2COOCH2CH3、－NHCH2CONH2、－NHCH2CH2OCH3、－NHCH2CH2OH、－NHCH2CH(OH)CH2OH和(iii)选自由以下组成的组中的部分。该化合物可用于在各种产品内提供清凉效果，例如食品、糖果、烟草产品、饮料、化妆品、牙粉、医疗制剂、漱口水和化妆用品。

Description

清凉化合物
本发明涉及清凉化合物。
清凉化合物，亦即赋予身体的皮肤或者粘膜凉爽感觉的化合物，是本领域已知的，且广泛地用于各种产品，例如食品、糖果、烟草产品、饮料、化妆品、牙粉、医疗制剂、漱口水和化妆用品中。
获得显著成功的一组清凉化合物由N-取代的对
Figure S2006800185961D00011
烷(menthane)酰胺组成。
现已发现，一些化合物显示出既令人惊奇地强烈，又持久的清凉效果。因此，提供一种方法，该方法提供皮肤或粘膜清凉效果且包括在其上施加至少一种式I的化合物：
Figure S2006800185961D00012
(a)其中B选自H、CH3、C2H5、OCH3、OC2H5和OH；和
(b)其中A是式-CO-D的一部分，其中D选自下述部分：
(i)-NR1R2，其中R1和R2独立地选自H和C1-C8直链或支链的脂族烷氧基烷基、羟烷基，芳脂族和环烷基；或R1和R2一起与它们连接到其上的氮原子形成一部分任选取代的5或6元杂环；
(ii)-NHCH2COOCH2CH3、-NHCH2CONH2、-NHCH2CH2OCH3、-NHCH2CH2OH、-NHCH2CH(OH)CH2OH和
(iii)选自由以下组成的组中的部分：
Figure S2006800185961D00021
和
Figure S2006800185961D00022
提供一种产品，该产品提供皮肤或粘膜清凉效果，它包括至少一种式I的化合物：
Figure S2006800185961D00023
(a)其中B选自H、CH3、C2H5、OCH3、OC2H5和OH；和
(b)其中A是式-CO-D的一部分，其中D选自下述部分：
(i)-NR1R2，其中R1和R2独立地选自H和C1-C8直链或支链的脂族烷氧基烷基、羟烷基，芳脂族和环烷基；或R1和R2与它们连接到其上的氮原子一起形成一部分任选取代的5或6元杂环；
(ii)-NHCH2COOCH2CH3、-NHCH2CONH2、-NHCH2CH2OCH3、-NHCH2CH2OH、-NHCH2CH(OH)CH2OH和
(iii)选自由以下组成的组中的部分：
和
Figure S2006800185961D00032
提供含式I的化合物：
Figure S2006800185961D00041
(a)其中B选自H、CH3、C2H5、OCH3、OC2H5和OH；和
(b)其中A是式-CO-D的一部分，其中D选自下述部分：
(i)-NR1R2，其中R1和R2独立地选自H和C1-C8直链或支链的脂族烷氧基烷基、羟烷基，芳脂族和环烷基；或R1和R2与它们连接到其上的氮原子一起形成一部分任选取代的5或6元杂环，条件是当B是H和A是-CONH2时，A与苯环的2-位或6-位连接；
(ii)-NHCH2COOCH2CH3、-NHCH2CONH2、-NHCH2CH2OCH3、-NHCH2CH2OH、-NHCH2CH(OH)CH2OH和
(iii)选自由以下组成的组中的部分：
和
Figure S2006800185961D00052
根据一些实施方案：
-A是-CONH2；和
-A在4位，和A是-CONHR3，其中R3选自C1-C4直链或支链脂族、烷氧基烷基或羟烷基。
根据其他实施方案：
-A是-CONH2；和
-A在4位，和A是-CONHR3，其中R3选自C1-C4直链或支链脂族、烷氧基烷基或羟烷基；和
-B是H。
可通过本领域已知的方法容易地制备并分离该化合物。
以上所述的一些化合物以许多立体化学形式获得。以上所述化合物的所有可能的立体化学形式包括在本发明的范围内。
它们与现有技术的其他清凉化合物的区别在于，它们令人惊奇地高的清凉效果(比已知化合物的清凉效果高最多10倍)和清凉效果的持久性，这增加了在大量的各种产品内的吸引力。
例如，询问一小组受试验者品尝清凉化合物的各种溶液，以及表明在2ppm下所述溶液具有类似于或者略高于
Figure S2006800185961D00061
醇(menthol)溶液的清凉强度。表1中示出了结果。
表1对清凉强度和持久性的实验
Figure S2006800185961D00062
根据表1，可看出式I化合物比对比的清凉化合物
Figure S2006800185961D00063
醇强最多10倍。式I的化合物也比现有技术最好的清凉化合物WS-3强得多。
可以且可允许共混两种或更多种本发明有用的化合物。另外，本领域已知的常规的清凉剂也可结合本发明的组合物一起使用。
所提供的化合物可在宽泛的各种产品中使用，所述产品将被施加到嘴或者皮肤上，以得到清凉的感觉。这种产品包括，但不限于，食品、糖果、烟草产品、饮料、化妆品、牙粉、医疗制剂、漱口水、化妆用品和类似物上。“施加”是指引起接触，例如口腔摄取，或者在烟草产品的情况下，吸入的任何形式。在施加到皮肤上的情况下，它可以是例如通过在霜或者药膏、可喷洒的组合物或类似组合物内包括该化合物。因此，还提供一种产品，该产品提供皮肤或粘膜清凉效果，所述产品包括以上所述的至少一种化合物。
在进一步的实施方案中，提供一种新型化合物。因此，提供式I的化合物：
Figure S2006800185961D00071
(a)其中B选自H、CH3、C2H5、OCH3、OC2H5和OH；和
(b)其中A是式-CO-D的一部分，其中D选自下述部分：
(i)-NR1R2，其中R1和R2独立地选自H和C1-C8直链或支链的脂族烷氧基烷基、羟烷基，芳脂族和环烷基；或R1和R2与它们连接到其上的氮原子一起形成一部分任选取代的5或6元杂环，条件是当B是H和A是-CONH2时，A与苯环的2-位或6-位连接；
(ii)-NHCH2COOCH2CH3、-NHCH2CONH2、-NHCH2CH2OCH3、-NHCH2CH2OH、-NHCH2CH(OH)CH2OH，和
(iii)选自由以下组成的组中的部分：
Figure S2006800185961D00081
实验
以下列出了本发明的非限定性实施例，这些实施例将描述各种实施方案。
实施例1
制备N-(4-酰胺基苯基)对
Figure S2006800185961D00082
烷酰胺
在4升烧瓶内，在2.5L甲苯中溶解256g对氨基苯甲酰胺和156g吡啶。在剧烈搅拌下，添加586g在甲苯内的～65％的对
Figure S2006800185961D00083
烷酰氯溶液。在室温下剧烈搅拌该棕灰色悬浮液过夜。过滤该悬浮液，并用MTBE(叔丁基甲基醚)和热水洗涤滤饼。在乙醇中重结晶该产品，得到290g具有下述光谱性能的所需产品的白色晶体：
m.p.：265-266℃
1H NMR(300MHz；d6-DMSO)δ：9.86(d，1H)，7.6(m，3H)，7.5(m，2H)，7.01(br.d，1H)，2.87(d，1H)，2.3(d，1H)，2.14(br.q，2H)1.81-1.32(m，5H)，1.16(br.s，1H)，0.89(d，3H)，0.8-0.1(m，6H)
13C NMR(75MHz；d6-DMSO)δ：174.1，167.2，141.7，128.3，128.0，117.9，48.5，43.4，34.0，31.6，28.2，26.6，23.3，22.0，21，15.9.
39ppm附近有一峰值在DMSO的信号中所掩盖。
实施例2
制备N-(3-酰胺基苯基)对
Figure S2006800185961D00091
烷酰胺
类似于实施例1所述的制备方法得到具有下述光谱性能的所需产品：
1H NMR(300MHz；CDCl3)δ：9.00(br.s，1H)，7.92(s，1H)，7.78(d，1H)，7.55(d，1H)，7.36(t，1H)，6.22(br.s，1H)，3.39-3.11(m，2H)，2.29(m，1H)，1.89-1.61(m，4H)，1.4-1.2(m，2H)，1.1-0.95(m，2H)，0.91(d，3H)，0.8(d，3H)，0.78(d，3H)
13C NMR(75MHz；CDCl3)δ：174.6，168，138.3，133.6，128.9，123.3，122.7，118.6，49.9，44.0，39.2，34.3，32.1，28.6，23.7，22，21.0，15.8
实施例3
制备N-(2-酰胺基苯基)对
Figure S2006800185961D00092
烷酰胺
类似于实施例1所述的制备方法得到具有下述光谱性能的所需产品：
1H NMR(300MHz；CDCl3)δ：11.27(s，1H)，8.68(d，1H)，7.56(d，1H)，7.48(t，1H)，7.05(t，1H)，6.44(br.s，1H)，5.89(br.s，1H)，2.24(td，1H)，1.92(d，1H)，1.82-1.52(m，4H)，1.41(br.s，1H)，1.35(quintuplet，1H)，1.14-0.95(m，2H)，0.91(d，3H)，0.84(d，3H)，0.83(d，3H)
13C NMR(300MHz；CDCl3)δ：175.0，171.1，140.2，133.1，127.1，122.2，121.3，118.2，51.4，44.5，39.3，34.4，32.0，28.7，23.8，22.1，21.1，15.9.
实施例4
制备4-[对
Figure S2006800185961D00093
烷羰基-氨基]-N-(2-甲氧基乙基)苯甲酰胺
类似于实施例1所述的制备方法得到具有下述光谱性能的所需产品：
MS：360([M+*])，345，328，302，286，194，162，136，120，83
实施例5
制备N-(4-(4-甲基哌嗪-1-羰基)苯基)对烷酰胺
类似于实施例1所述的制备方法得到具有下述光谱性能的所需产品：
MS：385([M+*])，370，286，120，99，83
实施例6
在口香糖内施加
胶料基础成分Flama-T*    25.180g
实施例1的化合物         0.100g
薄荷油                  1.000g
玉米糖浆                17.220g
糖                      55.170g
甘油                    1.330g
*Flama-T是Cafosa胶料，Barcelona(西班牙)的商品名
在预热的胶料基础成分内混合所有成分。以厚的膜形式铺开该混合物，冷却并切割成棒。试验者咀嚼胶料棒15分钟并吐出。当咀嚼时，在嘴的所有区域内感受到一致的清凉感觉。当吐出时，清凉感觉变得强烈且持续数小时。
实施例7
在牙膏内施加
不透明的牙齿凝胶                        99.500g
实施例3的化合物作为在薄荷油内5％的凝胶  0.500g
在牙齿凝胶内混合各化学品，在牙刷上放置一块牙齿凝胶，和试验者刷牙。用水漂洗嘴部，并吐出水。试验者在嘴的所有区域内感觉到强烈的清凉感觉。清凉感持续数小时。
要理解，此处所述的实施方案仅仅是例举，本领域的技术人员可在没有脱离本发明的精神和范围的情况下，作出各种变化和改性。所有这些变化和改性打算包括在以上所述的本发明的范围内。此外，所公开的所有实施方案不一定在替代方案内，因为可结合本发明的各种实施方案来提供所需的结果。

Claims (10)

1.向皮肤或粘膜提供清凉效果的方法，该方法包括在其上施加至少一种式I的化合物：
(a)其中B选自H、CH3、C2H5、OCH3、OC2H5和OH；和
(b)其中A是式-CO-D的结构部分，其中D选自下述部分：
(i)-NR1R2，其中R1和R2独立地选自H和C1-C8直链或支链的脂族烷氧基烷基、羟烷基，芳脂族和环烷基；或R1和R2与它们连接到其上的氮原子一起形成任选取代的5或6元杂环的一部分；
(ii)-NHCH2COOCH2CH3、-NHCH2CONH2、-NHCH2CH2OCH3、-NHCH2CH2OH、-NHCH2CH(OH)CH2OH和
(iii)选自由以下组成的组中的部分：
Figure S2006800185961C00012
Figure S2006800185961C00021
和
2.权利要求1的方法，其中A选自下述：
-A是-CONH2；和
-A在4位，且是-CONHR3，其中R3选自C1-C4直链或支链脂族、烷氧基烷基或羟烷基部分。
3.权利要求2的方法，其中B是H。
4.一种产品，该产品向皮肤或粘膜提供清凉效果，它包括至少一种式I的化合物：
Figure S2006800185961C00023
(a)其中B选自H、CH3、C2H5、OCH3、OC2H5和OH；和
(b)其中A是式-CO-D的结构部分，其中D选自下述部分：
(i)-NR1R2，其中R1和R2独立地选自H和C1-C8直链或支链的脂族烷氧基烷基、羟烷基，芳脂族和环烷基；或R1和R2与它们连接到其上的氮原子一起形成任选取代的5或6元杂环的一部分；
(ii)-NHCH2COOCH2CH3、-NHCH2CONH2、-NHCH2CH2OCH3、-NHCH2CH2OH、-NHCH2CH(OH)CH2OH和
(iii)选自由以下组成的组中的部分：
Figure S2006800185961C00031
和
Figure S2006800185961C00032
5.权利要求4的产品，其中A选自下述：
-A是CONH2；和
-A在4位，且是-CONHR3，其中R3选自C1-C4直链或支链脂族、烷氧基烷基或羟烷基部分。
6.权利要求5的产品，其中B是H。
7.权利要求4的产品，其中产品是食品、糖果、烟草产品、饮料、化妆品、牙粉、医疗制剂、漱口水或化妆用品中的至少一种。
8.含式I的化合物：
Figure S2006800185961C00041
(a)其中B选自H、CH3、C2H5、OCH3、OC2H5和OH；和
(b)其中A是式-CO-D的结构部分，其中D选自下述部分：
(i)-NR1R2，其中R1和R2独立地选自H和C1-C8直链或支链的脂族烷氧基烷基、羟烷基，芳脂族和环烷基；或R1和R2与它们连接到其上的氮原子一起形成任选取代的5或6元杂环的一部分，条件是当B是H和A是-CONH2时，A在苯环的2-位或6-位连接；
(ii)-NHCH2COOCH2CH3、-NHCH2CONH2、-NHCH2CH2OCH3、-NHCH2CH2OH、-NHCH2CH(OH)CH2OH和
(iii)选自由以下组成的组中的部分：
Figure S2006800185961C00042
和
Figure S2006800185961C00052
9.权利要求8的化合物，其中A选自下述：
-A是CONH2；和
-A在4位，且是-CONHR3，其中R3选自C1-C4直链或支链脂族、烷氧基烷基或羟烷基部分。
10.权利要求9的化合物，其中B是H。
CNA2006800185961A 2005-05-27 2006-05-24 清凉化合物 Pending CN101184470A (zh)

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