CN101277919A - 6-甲氧基-2,6-二甲基辛醛及其作为香料成分的用途 - Google Patents
6-甲氧基-2,6-二甲基辛醛及其作为香料成分的用途 Download PDFInfo
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- CN101277919A CN101277919A CNA2006800338948A CN200680033894A CN101277919A CN 101277919 A CN101277919 A CN 101277919A CN A2006800338948 A CNA2006800338948 A CN A2006800338948A CN 200680033894 A CN200680033894 A CN 200680033894A CN 101277919 A CN101277919 A CN 101277919A
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- Prior art keywords
- methoxyl group
- dimethyl
- methyl
- dimethyl octanal
- fragrance
- Prior art date
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- 239000003205 fragrance Substances 0.000 title claims abstract description 32
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- 239000004615 ingredient Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 6
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- XMLIBBMPASIZBW-UHFFFAOYSA-N 6-methoxy-2,6-dimethyloctanal Chemical compound CCC(C)(OC)CCCC(C)C=O XMLIBBMPASIZBW-UHFFFAOYSA-N 0.000 abstract 1
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Abstract
6－甲氧基－2，6－二甲基辛醛、它的制备方法和含有它的香料组合物。
Description
本发明涉及具有海、海洋、新鲜空气、青香、果香、柑橘的气味香型的6-甲氧基-2，6-二甲基辛醛，它的制备方法和包含它的香料组合物。
在香料业中持续需要提高或改善气味香型，或者赋予新的气味香型的新化合物。尤其，与新鲜的水环境(海滨、山湖等)有关的气味香型最近在香料中越来越盛行。
已经发现，之前的文献中从未描述过的6-甲氧基-2，6-二甲基辛醛具有器官感觉性质，已发现这种性质可以用于并且值得用于制备香料、香料组合物和香料产品。令人惊讶地发现，与6-甲氧基-2，6-二甲基庚醛(MethoxymelonalTM)相比，本发明的化合物的特征在于其结构虽然与6-甲氧基-2，6-二甲基庚醛非常相近，但是气味槛限浓度低约2.5倍。尽管MethoxymelonalTM令人想起木质气味，但6-甲氧基-2，6-二甲基辛醛更近于柑橘气味，而且具有更欢快、清爽和清新的气味香型。
气味槛限浓度定义为在空气中可以被嗅觉检测出来的有气味物质的蒸气的最低浓度。所述浓度可以通过使用嗅觉测量法或者通过使用能够让评审小组人员嗅到呈现的顶部空间的嗅瓶来测定。
正是由于6-甲氧基-2，6-二甲基辛醛的低的气味槛限浓度，因此在香料组合物中可以使用较低含量的该化合物浓度来获得嗅觉效果。
因此，本发明的一个方面涉及6-甲氧基-2，6-二甲基辛醛作为香料成分的用途。
本发明的化合物含有两个手性中心，这样就可以作为立体异构体混合物存在，或者其可以被拆分为异构纯的形式。立体异构体的拆分给这些化合物的制备和纯化增加了复杂性，因此仅仅出于经济原因优选使用作为立体异构体的混合物形式的6-甲氧基-2，6-二甲基辛醛。但是，如果希望制备单独的立体异构体，则可以根据现有技术中已知的方法，例如制备性HPLC和GC或者立体选择性合成来实现。
本发明的化合物可以用在大范围的香料应用中，例如用在精细和功能性香料的任何领域，例如香水、家用产品、洗涤产品、身体护理产品和化妆品中。取决于特定应用以及其它增味剂成分的性质和含量，该化合物可以以大大不同的用量来使用。非常概括地可以说，6-甲氧基-2，6-二甲基辛醛是一种非常强烈的增味剂，因此以非常低的剂量，例如0.01wt％就已经可以获得效果。另一方面，如果与最佳结合成分结合使用其甚至可以以非常高的浓度使用。优选的浓度为约0.01wt％-约15wt％，优选为终产品地0.1-5wt％。但是，这些值只是以例子的形式给出，因为有经验的香料商还可以由较低或较高的浓度获得效果或者可以得到新产品。
在一个实施方案中，可以以0.1-3wt％的量将6-甲氧基-2，6-二甲基辛醛用在洗发香波中。在另一个实施方案中，可以以0.1-20wt％，更优选0.1-5wt％的量将6-甲氧基-2，6-二甲基辛醛用在精细香料中。
通过与基料混合本发明的化合物可以用于产生非常宽谱系的香料组合物。如本文中所用的，“基料”包括选自目前能够获得的大范围天然产品和合成分子的所有已知的增味剂分子，例如精油；醇类、醛类和酮类；醚类和缩醛类；酯类和内酯类；大环化合物类和杂环化合物类，和/或与一种或多种通常与香料组合物中的增味剂结合使用的成分或赋型剂，例如载体物质，以及其它常用在本领域中的助剂混合。因此，对于果香/甜瓜、柑橘特性的香料组合物而言，6-甲氧基-2，6-二甲基辛醛赋予其新鲜特性并且消除了新鲜空气/甜瓜香型的刺激性。
以下所列的物质包括可与本发明化合物结合的已知增味剂分子的实例：
-精油和提取物，例如，树苔净油、罗勒油、海狸香、广木香油、香桃木油、橡树苔净油、香叶油、茉莉净油、广藿香油、玫瑰油、檀香油、苦艾油、薰衣草油或依兰-依兰油；
-醇类，例如，香茅醇、EbanolTM、丁子香酚、法呢醇、香叶醇、Super MuguetTM、里哪醇、苯乙醇、SandaloreTM、萜品醇或TimberolTM；
-醛类和酮类，例如，α-戊基肉桂醛、GeorgywoodTM、羟基香茅醛、Iso E Super
、Isoraldeine
、Hedione
、麦芽酚、甲基柏木酮、甲基紫罗兰酮或香兰素；
-醚类和缩醛类，例如，AmbroxTM、香叶基甲基醚、氧化玫瑰或SpirambreneTM；
-酯类和内酯类，例如，乙酸苄基酯、乙酸柏木酯、γ-癸内酯、Helvetolide
、γ-十一烷酸内酯或乙酸岩兰草酯；
-大环化合物类，例如，黄葵内酯、十三烷二酸亚乙基酯或Exaltolide
；
-杂环化合物类，例如，异丁基喹啉。
简单地通过将香料组合物与香料用品直接混合就可以将上述化合物用在香料用品中，或者可以在之前的步骤中用捕集物质对其进行捕集，所述捕集物质例如为聚合物、胶囊、微胶囊和纳米胶囊、脂质体、膜形成物、吸收剂，例如碳或沸石、环状低聚糖及其混合物，或者其可以化学键合在基质上，键合后的物质在经历诸如光、酶等的外部刺激时易于释放6-甲氧基-2，6-二甲基辛醛，随后释放物再与用品混合。
因此，本发明还提供一种制备香料用品的方法，包括使用常规技术和方法将6-甲氧基-2，6-二甲基辛醛直接混入用品中，或者混合包含6-甲氧基-2，6-二甲基辛醛的香料组合物，随后可以再将其混入到香料用品中，从而将6-甲氧基-2，6-二甲基辛醛作为香料成分结合进来。
如本文中所用的，“香料用品”意指包含增味剂的任何产品，例如精细香料，例如香水和装饰香水；家用产品，例如洗碗机用的洗涤剂、表面清洁剂；洗涤产品，例如软化剂、漂白剂、洗涤剂；身体护理产品，例如洗发香波、洗浴胶；化妆品，例如除臭剂、雪花膏；和空气清新剂。该列产品只是用于说明，不应将其视为以任何方式进行限制。
现在参考下列非限制性实施例进一步描述本发明。
实施例1：6-甲氧基-2，6-二甲基辛醛的合成
A)6-甲氧基-6-甲基-2-辛酮
在3℃下经40分钟向2kg 6-甲基-辛-5-烯-2-酮在4升甲醇中形成的溶液中加入800ml浓硫酸。室温下再搅拌5小时后将溶液倾倒到8kg冰水中，并用叔丁基甲基醚萃取。用20％的Na2CO3(200ml)和浓NaCl溶液(3×150ml)洗涤结合起来的有机相。除去溶剂后在70cm Sulzer柱上蒸馏剩余物，得到840g回收的原料(沸点：72°-75℃/10mmHg)和970g 6-甲氧基-6-甲基-2-辛酮(bp.：95°-98℃/10Torr＝13.3mbar)。
1H-NMR(400MHz，CDCl3)：δ0.84(t，J＝7.6Hz，3H)，1.09(s，3H)，1.38-1.61(m，6H)，2.14(s，3H)，2.44(t，J＝7.2Hz，2H)，3.14(s，3H)。
IR：1715cm-1。
B)3-(4-甲氧基-4-甲基-己基)-3-甲基-氧杂环丙烷-2-甲酸甲酯
在氮气氛下将860g 6-甲氧基-6-甲基-2-辛酮、4升叔丁基甲基醚和648g氯代乙酸甲酯冷却至0℃。在进一步的冷却下经20分钟分6份加入350g甲氧基钠(sodium methoxyde)。然后在室温下搅拌，直至观察(GC)不到还有酮被消耗掉。冷却至0℃后，加入1升5％的乙酸(w/w)并分离各相。水相用叔丁基甲基醚(500ml)萃取。用水、浓KHCO3溶液、浓NaCl溶液洗涤结合的有机相并在MgSO4上干燥。在小的Vigreux-柱上对除去溶剂之后所剩的黄色油进行蒸馏，得到823g 3-(4-甲氧基-4-甲基-己基)-3-甲基-氧杂环丙烷-2-甲酸甲酯(异构体的混合物，沸点：115°-128°/0.3Torr＝0.399mbar)。
1H-NMR(400MHz，CDCl3)：δ0.8-0.88(m，3H)，1.07-1.09(m，3H)，1.35-1.75(m，11H)，3.12-3.15(m，3H)，3.34-3.36(m，1H)，3.78(s)和3.79(s，全部3H)。
MS：87(100％)。
C)6-甲氧基-2，6-二甲基-辛醛
在0℃-5℃下经2小时将溶解在800ml水中的180g氢氧化钾加入到810g 3-(4-甲氧基-4-甲基-己基)-3-甲基-氧杂环丙烷-2-甲酸甲酯中。然后逐份加入溶解在150ml水中的36g KOH直至颜色由橙色变为持续的米色。然后在0℃下加入32％的HCl(300ml，经30分钟加入)，以对pH为11的混合物进行酸化，之后用磷酸稀释至pH为3。分离各相，水相用叔丁基甲基醚萃取。在蒸发溶剂之前用浓NaCl溶液洗涤结合的有机相。经3小时将剩下的非常粘稠的油(780g)滴加至保持在160℃下的300ml PEG 200中。这样蒸除产物。添加之后注入蒸汽约30分钟以馏去任何蒸汽-挥发性产物。分离馏出物的两相，水相用叔丁基甲基醚萃取。用KHCO3和NaCl洗涤结合的有机相。蒸发溶剂得到380g浅黄色的油，在60cm Sulzer柱上对其进行蒸馏得到338g 6-甲氧基-2，6-二甲基-辛醛(bp.65°-66℃/0.3Torr＝0.399mbar)。
1H-NMR(400MHz，CDCl3)：δ0.83(t，J＝7.6Hz，3H)，1.07(s，3H)，1.1(d，J＝7.2Hz，3H)，1.28-1.52(m，7H)，1.66-1.76(m，1H)，2.31-2.42(m，1H)，3.12(s，3H)，9.62(d，J＝1.6Hz，1H)。
实施例2：使用嗅觉计测量的气味槛限浓度
嗅觉计按照在载气中线性稀释增味剂的原则工作。替换的增味剂的量取决于其蒸气压和载气流速。受流速调节器控制的恒定流速的氮气将增味剂从试样容器载至混合室中。在混合室中用无色空气稀释载气-增味剂混合物。使一部分经稀释的有气味的空气由混合室经熔凝的二氧化硅毛细管到达探查漏斗。流经毛细管的流速决定从混合室进入探查漏斗的有味空气的量，该流速取决于阀的开启，在二元步骤中可以经由PC将所述阀调节为1-256ml。通过用无味空气以8L/min的流速恒定地冲刷有味空气试样的最终稀释物而使其出现在玻璃漏斗内。通过特殊的自动化管道设置装置实现强制选择的三角形外观，其中仅有唯一的开关位置能使经过毛细管输送的增味剂进入到探查漏斗内，而在其它两个位置处毛细管被设置在漏斗外面，在该处流出物被吸走。每次试验后自动地以随机的顺序改变管道设置。由施加在嗅觉计上的增味剂蒸气压和稀释比计算浓度，假设在试样发生器中实现了蒸汽饱和。从毛细管流出物中抽出已知体积的试样进入顶部过滤器，之后确定其浓度作为空白。
评审小组人员在能感觉到中等强度增味剂的浓度水平下开始在嗅觉计上闻。在三个同样水平的连续试验(或者五个试验中的四个恰当的试验)中，借助两个因素中的一个将刺激物的浓度降至下一个较低水平，等等的水平上，直至评审小组人员达到他的槛限值水平。
在同样的条件下测定6-甲氧基-2，6-二甲基辛醛和6-甲氧基-2，6-二甲基庚醛的气味槛限浓度，并由12个评审小组人员进行比较。改变评审小组人员闻两个化合物的起始顺序。在同一天测定两个化合物，获得下列数据：
气味槛限浓度[ng/L]
化合物 几何平均值
6-甲氧基-2，6-二甲基辛醛 0.78
6-甲氧基-2，6-二甲基庚醛 1.92
从上述结果可以看出，与现有技术的化合物相比本发明的化合物具有低出2.46倍的槛限值。基于此，由于赋予同样的嗅觉效果只需少得多的所要求的化合物，因此实现了显著的进步。
实施例3：花香香料组合物
重量份
里哪醇(Givaudan) 30
Mayol(Firmenich) 25
二氢β紫罗兰酮(Givaudan) 8
β紫罗兰酮(Givaudan) 8
Cepionate(二氢茉莉酮酸甲酯) 250
环己醛 20
二氢法呢醛(3，7，11-三甲基-6，10-十二碳二烯醛) 20
合成法呢醇(3，7，11-三甲基十二碳-2，6，10-三烯-1-醇) 20
苯甲酸顺式-3-己烯酯 25
水杨酸顺式-3-己烯酯 25
合成羟基香茅醛 30
Dimetol
(2，6-二甲基-2-庚醇) 8
Hedione(Firmenich) 300
麝香酮(4′-叔丁基-2′，6′-二基-3′，5′-二硝基苯乙酮) 4
Cassis Base 345 FH(复合香料香基，Firmenich) 3
Indolene(CAS 67860-00-8)10％，在DPG中 12
羟乙酸烯丙基戊基酯10％，在DPG中 2
N 112(4-(对羟基苯基)-2-丁酮)10％，在DPG中 5
α大马酮10％，在DPG中 8
乙基里哪醇 25
柠檬醛二甲缩醛 2
顺式茉莉酮(CAS 488-10-8)10％，在DPG中 5
Galaxolide
50 IPM(1，3，4，6，7，8-六氢-4，6，6，7，8，8-
六甲基-环戊-γ-2-苯并吡喃) 20
Phenoxanol
(3-甲基-5-苯基-1-戊醇) 3
异丁酸对甲苯酯1％，在DPG中 2
二丙二醇(DPG) 130
加入10份6-甲氧基-2，6-二甲基辛醛使上述组合物更自然、圆满和清新。其还给该花香果香的香花香型带来奇异的湿润内涵，而且还有助于开发有吸引力的空气-海洋花香气味。
实施例2：男性香料组合物
重量份
羟乙酸烯丙基戊基酯 1
Ambrofix(Givaudan) 2
水杨酸苄酯 100
乙酸香茅酯 2
α大马酮10％，在DPG中 9
二氢月桂烯醇 10
乙酸二甲基苄基甲基酯 8
丁酸二甲基苄基甲基酯 3
Pharaone(2-环己基-1，6-庚二烯-3-酮)10％，在DPG中 8
乙酸香叶酯 3
葡萄柚精油 70
Azurone(7-(3-甲基丁基)-2H-1，5-苯并二氧杂-3(4H)-酮)
1％，在DPG中 2
Habanolide
(氧杂环十六碳烯-2-酮) 100
Georgywood(顺式-1-(1，2，3，4，5，6，7，8-八氢-1，2，8，8-
四甲基-2-萘基)-乙酮) 250
顺式-3-己烯醇 3
乙酸顺式-3-己烯酯 1
水杨酸顺式-3-己烯酯 10
己基肉桂醛 45
Hedione(3-氧代-2-戊基-环戊烷乙酸甲酯) 150
香橼精油 45
环己醛 20
里哪醇 15
合成乙酸里哪醇酯 45
橙精油 25
Oranger Cristals(1-(2-萘基)-乙酮)10％，在DPG中 2
Gardenol 5
萜品醇提纯物 3
Cyclal C(2，4-二甲基环己-3-烯甲醛)10％，在DPG中 14
二丙二醇(DPG) 19
加入30份6-甲氧基-2，6-二甲基辛醛给上述组合物带来清新、活泼和舒适感。其还给最佳性质直至变干性都带来了清新的海洋特性，提高了最佳性质的明亮性并且给木质麝香的变干性保持天然的清新。
Claims (6)
1、6-甲氧基-2，6-二甲基辛醛。
2、6-甲氧基-2，6-二甲基辛醛作为香料成分的用途。
3、包含6-甲氧基-2，6-二甲基辛醛的香料组合物。
4、包含6-甲氧基-2，6-二甲基辛醛的香料用品。
5、根据权利要求3的香料用品，其中所述香料用品为香水、家用产品、洗涤产品、身体护理产品或化妆品。
6、一种制备香料用品的方法，包括结合6-甲氧基-2，6-二甲基辛醛的步骤。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05020309.0 | 2005-09-16 | ||
| EP05020309A EP1764355A1 (en) | 2005-09-16 | 2005-09-16 | 6-methoxy-2,6-dimethyloctanal and its use as a fragrance ingredient |
| PCT/CH2006/000501 WO2007030967A1 (en) | 2005-09-16 | 2006-09-15 | 6-methoxy-2,6-dimethyloctanal and its use as a fragrance ingredient |
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| Publication Number | Publication Date |
|---|---|
| CN101277919A true CN101277919A (zh) | 2008-10-01 |
| CN101277919B CN101277919B (zh) | 2011-04-13 |
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| CN2006800338948A Active CN101277919B (zh) | 2005-09-16 | 2006-09-15 | 6-甲氧基-2,6-二甲基辛醛及其作为香料成分的用途 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7790668B2 (zh) |
| EP (2) | EP1764355A1 (zh) |
| JP (1) | JP4987004B2 (zh) |
| CN (1) | CN101277919B (zh) |
| AT (1) | ATE420846T1 (zh) |
| BR (1) | BRPI0616232B1 (zh) |
| DE (1) | DE602006004888D1 (zh) |
| ES (1) | ES2318776T3 (zh) |
| MX (1) | MX2008003199A (zh) |
| WO (1) | WO2007030967A1 (zh) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104704096A (zh) * | 2012-10-08 | 2015-06-10 | 帝斯曼知识产权资产管理有限公司 | 香味和芳香配制物(ii) |
| CN107072913A (zh) * | 2014-09-25 | 2017-08-18 | 宝洁公司 | 包含离子液体的芳香剂组合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5579483B2 (ja) * | 2010-04-07 | 2014-08-27 | 三井化学アグロ株式会社 | 分岐脂肪族アルデヒドの製造方法 |
| GB201006042D0 (en) * | 2010-04-12 | 2010-05-26 | Givaudan Sa | Improvements in or relating to organic compounds |
| WO2013053102A1 (en) * | 2011-10-11 | 2013-04-18 | Givaudan Sa | Improvements in or relating to organic compounds |
| WO2018069458A1 (en) * | 2016-10-12 | 2018-04-19 | Dsm Ip Assets B.V. | Process for the manufacture of 6-methoxy-2,6-dimethylheptanal |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3963648A (en) * | 1972-09-08 | 1976-06-15 | Bush Boake Allen Limited | Perfume chemicals |
| GB1555333A (en) * | 1975-05-29 | 1979-11-07 | Bush Boake Allen Ltd | Perfumery compositions comprising hydroxy- or alkoxy-substituted c9 alkanals alkanols and esters |
| JP3271785B2 (ja) * | 1992-02-20 | 2002-04-08 | 長谷川香料株式会社 | ８−ヒドロキシ−８−メチルノナナールを含有する香料組成物 |
| JP2002542380A (ja) * | 1999-04-20 | 2002-12-10 | ザ、プロクター、エンド、ギャンブル、カンパニー | 芳香剤原料アルデヒドおよび第三級α炭素原子をもつ芳香剤原料前駆体 |
| JP2002206098A (ja) * | 2001-01-09 | 2002-07-26 | Tetsuo Watanabe | 黒トリュフ香気成分の組成物ならびに製造方法 |
| ES2371437T3 (es) * | 2003-11-06 | 2012-01-02 | Firmenich Sa | Aldehido como ingrediente perfumante o aromatizante. |
-
2005
- 2005-09-16 EP EP05020309A patent/EP1764355A1/en not_active Withdrawn
-
2006
- 2006-09-15 WO PCT/CH2006/000501 patent/WO2007030967A1/en active Application Filing
- 2006-09-15 EP EP06775194A patent/EP1924544B1/en active Active
- 2006-09-15 US US12/065,407 patent/US7790668B2/en active Active
- 2006-09-15 CN CN2006800338948A patent/CN101277919B/zh active Active
- 2006-09-15 MX MX2008003199A patent/MX2008003199A/es active IP Right Grant
- 2006-09-15 DE DE602006004888T patent/DE602006004888D1/de active Active
- 2006-09-15 ES ES06775194T patent/ES2318776T3/es active Active
- 2006-09-15 JP JP2008530294A patent/JP4987004B2/ja active Active
- 2006-09-15 AT AT06775194T patent/ATE420846T1/de not_active IP Right Cessation
- 2006-09-15 BR BRPI0616232-0A patent/BRPI0616232B1/pt active IP Right Grant
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104704096A (zh) * | 2012-10-08 | 2015-06-10 | 帝斯曼知识产权资产管理有限公司 | 香味和芳香配制物(ii) |
| CN104704096B (zh) * | 2012-10-08 | 2020-09-29 | 帝斯曼知识产权资产管理有限公司 | 香味和芳香配制物(ii) |
| CN107072913A (zh) * | 2014-09-25 | 2017-08-18 | 宝洁公司 | 包含离子液体的芳香剂组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US7790668B2 (en) | 2010-09-07 |
| MX2008003199A (es) | 2008-03-18 |
| ATE420846T1 (de) | 2009-01-15 |
| EP1924544A1 (en) | 2008-05-28 |
| DE602006004888D1 (de) | 2009-03-05 |
| BRPI0616232A2 (pt) | 2011-06-14 |
| CN101277919B (zh) | 2011-04-13 |
| EP1924544B1 (en) | 2009-01-14 |
| JP4987004B2 (ja) | 2012-07-25 |
| JP2009509934A (ja) | 2009-03-12 |
| WO2007030967A1 (en) | 2007-03-22 |
| BRPI0616232B1 (pt) | 2021-06-22 |
| US20080261860A1 (en) | 2008-10-23 |
| ES2318776T3 (es) | 2009-05-01 |
| EP1764355A1 (en) | 2007-03-21 |
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