CN111770980A - 乙基香草醛和乙基香草醛衍生物的气味缩醛 - Google Patents
乙基香草醛和乙基香草醛衍生物的气味缩醛 Download PDFInfo
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- CN111770980A CN111770980A CN201880082296.2A CN201880082296A CN111770980A CN 111770980 A CN111770980 A CN 111770980A CN 201880082296 A CN201880082296 A CN 201880082296A CN 111770980 A CN111770980 A CN 111770980A
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- oil
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- flavour
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- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 title description 18
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- 239000000796 flavoring agent Substances 0.000 claims abstract description 53
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- -1 acetal compound Chemical class 0.000 claims description 45
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- 239000000047 product Substances 0.000 claims description 17
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- 150000002576 ketones Chemical class 0.000 description 5
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 5
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
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- WRFZKAGPPQGDDQ-UHFFFAOYSA-N valeryl hexanoate Chemical compound CCCCCOC(=O)CCCCC WRFZKAGPPQGDDQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
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Abstract
本发明涉及新的气味缩醛,其用作香味或风味材料,特别是用于提供具有类似香草净油的天然印象的香草和辛辣香调。
Description
发明领域
本发明涉及新的气味缩醛,其用作香味或风味材料,特别是用于提供具有类似香草净油的天然印象的香草和辛辣香调。
发明背景
取代的2-烷氧基苯酚在食品和香味组合物中具有广泛的应用。例如香草醛、乙基香草醛、甲基丹提力士、丁香酚或香荚兰醇(Ultravanil)用于在香味和风味组合物中获得甜、辛辣和烟熏香调。特别地,需要具有优异性能并且比例如香草醛更空气稳定的新型香脂和香草香调;例如,WO2011132098公开了碳酸烷基芳基酯作为加香成分以赋予辛辣和/或香脂香调,特别是香草类型的香调。
通常,2-烷氧基苯酚在香味中的使用具有某些局限性,这是由于它们在碱性介质(例如皂、洗发剂、洗衣粉)中的相当低的性能,因为它们在空气中和在某些产品中具有脱色的倾向,这是酚类的固有性质。这些限制可以通过酚OH基的官能化来克服,其防止非挥发性苯氧基阴离子的形成并延迟芳环的氧化。然而,对于大多数具有受保护羟基的香草化合物,气味强度降低,并且气味香调可能不同于母体化合物。而且,保护基的气味性质可导致在老化产品中存在令人不愉快的异味。例如,乙基香草醛乙酸酯或香草醛异丁酸酯在水解时可产生腐臭/酸性异味。值得注意的是,由于香草醛结构的小变化引起气味的显著变化,因此具有香草气味的气味剂数量有限。例如,异香草醛气味弱得多(几乎无气味)并且主要是草本的。因此,开发以香草气味为特征但在香味基料中稳定的新分子仍然是一个挑战。下面是最重要的以香草气味为特征的市售化合物:
香荚兰醇:香草味、甜、酚类
乙基香草醛:甜、奶油味、香草味、焦糖味
异丁酸香兰酯:香草味、甜、果味
香草醛:甜、香草味、奶油味、巧克力味
乙基香草醛丙二醇缩醛:甜、香草味、奶油味、辛辣
甲基丹提力士:辛辣、康乃馨味、甜、香草味
公开了2-烷氧基苯酚的羟基与羧酸形成酯(例如,异丁酸香兰酯(US4473588)或烷基碳酸酯(WO2011132098))。然而,这种酯的形成伴随着产生大量的废物。由于从环境和经济的角度来看,减少化学过程中形成的废物是至关重要的,因此我们寻找用于酚基官能化的替代方法。这些方法应该允许产生新的具有香草香调的芳香物质,并且具有减少废物的量或更优选地消除废物的额外优点。因此,我们将注意力转到使用乙醛乙缩醛作为羟基部分的保护基团,其可以通过使用布朗斯台德酸作为催化剂使酚与乙氧基乙烯反应以100%原子经济性引入。
香草醛的缩醛是作为用于药物产品(抗高血压剂)的合成中间体(US3636158A)制备的,然而,该分子没有公开嗅觉特性。值得注意的是,迄今为止,没有报道提供香草样香味的乙醛乙缩醛。
发明概述
本发明公开了式(1)、式(2)、式(3)或式(4)的新化合物及其在香味、风味和/或除臭/掩蔽组合物中的用途。
下面公开的新缩醛具有清晰的香草样特征,并且与它们的母体酚相比,具有更高的直接性和持久性。它们高度保留了母体酚的气味,同时轻微改变了气味分布。此外,新缩醛在介质如烛用蜡和皂中具有提高的空气稳定性和光稳定性。
详细描述
表征本发明化合物的术语"气味剂"是指在人中,它引发优选令人愉快的气味感觉;因此,它通常用于给工业和卫生制品、洗涤剂、清洁剂、个人卫生产品、化妆品等加香。对于本发明和所附权利要求书来说,术语"气味剂"包括"芳香物质"。芳香物质是通常用于表示向食品提供气味和/或风味的物质的术语。
式(1)、式(2)、式(3)或式(4)的缩醛化合物可以单独使用,作为其混合物使用,或与基础材料组合使用。
如本文所用,"基础材料"包括所有已知的香味/风味材料,其选自广泛范围的天然产物,如:精油、提取物、类树脂或分离物和目前可获得的合成材料,例如:烃、醇、醛和酮、醚和缩醛、酯和内酯、腈、肟或杂环,和/或与一种或多种通常与香味和/或风味组合物中的气味剂结合使用的成分或赋形剂/辅助剂混合,例如:溶剂/稀释剂、稳定剂、载体材料和本领域常用的其它助剂。
式(1)、式(2)、式(3)或式(4)的缩醛化合物可以用于宽范围的香味应用,例如在精细和功能香味的任何领域中,如香水、空气护理产品、家用产品、洗衣产品、身体护理产品和化妆品。根据具体应用和其它气味剂成分的性质和数量,可以广泛变化的量使用所述化合物。
根据本发明的一个优选的实施方式,本发明的香味、风味和/或除臭/掩蔽组合物包含至少一种如前所述的式(1)、式(2)、式(3)或式(4)的缩醛化合物,其量为0.0001-95重量%,例如0.001-25重量%,优选0.01-15重量%,更有利地0.1-10重量%,尤其是1-5重量%,在每种情况下都是相对于整个组合物。
根据本发明的一个特别优选的实施方式,除了本发明的式(1)、式(2)、式(3)或式(4)的化合物之外,本发明的香味、风味和/或除臭/掩蔽组合物还包含另外的气味剂,例如相对于整个香味和/或风味组合物,其量为0.1-99.9重量%,优选5-90重量%,特别是15-70重量%。
如上所述的式(1)、式(2)、式(3)或式(4)的化合物可以简单地通过将至少一种式(1)、式(2)、式(3)或式(4)的化合物与消费品基料直接混合而用于消费品基料中;或者在较早的步骤中,它们可以用捕集材料捕集,例如聚合物、胶囊、微胶囊和/或纳米胶囊、脂质体、成膜剂、吸收剂如活性炭或沸石、环状低聚糖、环状甘脲、以及它们中两种或更多种的混合物,或者它们可以化学键合到基材上,然后与消费品基料混合,所述基材适于在施加外部刺激如光、酶、空气、水等后释放香味分子。
因此,本发明可用于制造香味、风味和/或除臭/掩蔽组合物的现有方法,所述方法包括使用常规技术和方法,通过将式(1)、式(2)、式(3)或式(4)的化合物直接混合到消费品基料中,或者通过混合包含所述式(1)、式(2)、式(3)或式(4)的化合物的香味、风味和/或除臭/掩蔽组合物,然后可将其与消费品基料混合,来掺入式(1)、式(2)、式(3)或式(4)的化合物作为香味、风味和/或除臭/掩蔽成分。通过加入嗅觉可接受量的至少一种如所述的本发明的式(1)、式(2)、式(3)或式(4)化合物,消费品基料的气味香调可得到改善、增强和/或改变。
本发明提供香味、风味和/或除臭/掩蔽组合物,所述组合物包含选自式(1)、式(2)、式(3)或式(4)化合物的缩醛。
其中化合物(1)是2-乙氧基-1-(1-乙氧基乙氧基)-4-甲基苯;化合物(2)是3-乙氧基-4-(1-乙氧基乙氧基)苯甲醛;化合物(3)是2-(3-乙氧基-4-(1-乙氧基乙氧基)苯基)-4-甲基-1,3-二氧戊环;化合物(4)是2-乙氧基-1-(1-乙氧基乙氧基)-4-(甲氧基甲基)苯。
申请人还发现,从嗅觉的角度来看,式(1)、式(2)、式(3)或式(4)的化合物具有明显的香草和辛辣香调,具有令人惊讶的类似香草净油或多香果油的自然印象。此外,与它们的母体酚气味剂,例如式(1)化合物的母体酚2-乙氧基-4-甲基苯酚(香荚兰醇)、式(2)化合物的母体酚3-乙氧基-4-羟基苯甲醛(乙基香草醛)、式(3)化合物的母体酚2-乙氧基-4-(4-甲基-1,3-二氧戊环-2-基)苯酚(乙基香草醛丙二醇缩醛)和式(4)化合物的母体酚2-乙氧基-4-(甲氧基甲基)苯酚(甲基丹提力士)相比,式(1)、式(2)、式(3)和式(4)化合物具有更高的直接性和持久性。它们高度保留了母体酚的气味,同时轻微改变了气味分布。与母体酚化合物相比,气味分布的变化列于下表中。
申请人还发现,缩醛在皂、烛用蜡和其它介质(例如用作香基的3-甲氧基-3-甲基-1-丁醇)中具有通常改进的颜色稳定性。例如,当式(1)化合物用于烛用蜡基料(例如,以0.3重量%浓度)时,在室温下在阳光照射位置放置四周后没有观察到材料变色,而当以相同的摩尔浓度使用母体酚2-乙氧基-4-甲基苯酚时,可以容易地观察到烛用蜡的泛黄。类似地,在相同条件下,与包含相应母体酚乙基香草醛和2-乙氧基-4-(4-甲基-1,3-二氧戊环-2-基)苯酚(乙基香草醛丙二醇缩醛)的对照样品相比,包含式(2)化合物和/或式(3)化合物的皂基(例如包含1重量%的化合物(2)的皂基或包含1重量%的化合物(3)的皂基)或包含式(2)化合物和/或式(3)化合物的香基(例如包含4重量%的化合物(2)的香基或包含4重量%的化合物(3)的香基)的变色显著更慢。
在本发明的一个实施方式中,要求保护的香味、风味和/或除臭/掩蔽组合物有利地用作香味组合物。本发明的香味组合物通常包括香料、古龙水、eau du toilette和/或eau de parfum。在本发明的一个实施方式中,要求保护的香味、风味和/或除臭/掩蔽组合物有利地用于化妆品制剂、个人护理产品、清洁产品、织物柔软剂和/或空气清新剂等。此外,在本发明实施方式的范围内,本文所述的新型香味、风味和/或除臭/掩蔽组合物和/或新型式(1)、式(2)、式(3)或式(4)化合物可以整合到建筑材料、墙壁和地板覆盖物、车辆组件等中。
在一个实施方式中,本发明还提供式(1)、式(2)、式(3)或式(4)的新化合物,其可用于本发明的香料、芳香和/或除臭/掩蔽组合物中。
其中化合物(1)是2-乙氧基-1-(1-乙氧基乙氧基)-4-甲基苯;化合物(2)是3-乙氧基-4-(1-乙氧基乙氧基)苯甲醛;化合物(3)是2-(3-乙氧基-4-(1-乙氧基乙氧基)苯基)-4-甲基-1,3-二氧戊环;化合物(4)是2-乙氧基-1-(1-乙氧基乙氧基)-4-(甲氧基甲基)苯。
在一个实施方式中,通过使用缩醛化合成步骤,式(1)、(2)、(3)和(4)的化合物可以有利地分别由式(5)、(6)、(7)、(8)的化合物制备。
可以使用任何合适的产生式(1)、(2)、(3)和(4)化合物的缩醛化方法;作为说明性和非限制性实例,例如通过使所述式(5)、(6)、(7)、(8)的化合物与乙氧基乙烯在催化量的酸(例如盐酸、硫酸、磷酸等)存在下在合适的溶剂(例如二氯甲烷、乙酸乙酯等)存在下反应进行缩醛化,或在无溶剂的情况下进行缩醛化,在无溶剂情况下乙氧基乙烯起到溶剂和反应物的作用。在本发明的一个实施方式中,缩醛(1)、(2)、(3)和(4)的合成因此可以根据以下方法实现:
通常,除了本文所述的新型气味剂和/或香味、风味和/或除臭/掩蔽组合物之外,合适的香味、风味或除臭组合物可以有利地包括常规成分,例如溶剂、载体、稳定剂、乳化剂、增湿剂、分散剂、稀释剂、增稠剂、冲淡剂、其它气味剂和/或辅助剂等。
式(1)、式(2)、式(3)或式(4)的化合物与许多已知的天然或合成的香味、风味和/或除臭/掩蔽材料相结合,从而天然成分的范围可不仅包括易挥发组分,而且还包括半挥发组分和微挥发组分,合成成分的范围可以包括来自多种物质的代表,如从以下非限制性汇编中将明显的:
天然产品如:
香旱芹油(Ajowan oil)、香树油(Amyris oil)、蒿草油(Armoise oil)、艾草油(Artemisia oil)、罗勒油(Basil oil)、蜂蜡净油(Bees wax absolute)、佛手柑油(Bergamot oil)、桦木焦油(Birch tar oil)、黑胡椒油(Black pepper oil)、黑胡椒油树脂(Black pepper oleoresin)、樟脑油(Camphor oil)、依兰油(Cananga oil)、藏茴香油(Caraway oil)、小豆蔻油(Cardamom oil)、胡萝卜籽油、海狸香净油(Castoreumabsolute)、雪松叶油(Cedar leaf oil)、雪松木油(Cedarwood oil)、芹菜籽油(Celeryseed oil)、春黄菊油(Chamomile oil)、桂皮油(Cinnamon bark oil)、桂叶油、岩蔷薇净油(Cistus absolute)、岩蔷薇油(Cistus oil)、香茅油(Citronella oil)、香茅萜(Citronella terpenes)、鼠尾草油(Clary sage oil)、精馏丁香油(Clove oilrectified)、康酿克油(Cognac oil white)、芫荽籽油(Coriander seed oil)、孜然籽油(Cumin seed oil)、柏树油(Cypress oil)、印蒿油(Davana oil)、莳萝籽油(Dill seedoil)、榄香脂油(Elemi oil)、榄香树脂型物(Elemi resinoid)、桉树油(Eucalyptus oil)、冷杉叶油(Fir needle oil)、白松香油(Galbanum oil)、天竺葵油(Geranium oil)、印度姜油(Ginger oil Indian)、葡萄柚油(Grapefruit oil)、愈创木油(Guaiacwood oil)、古芸香胶(Gurjun balsam)、茉莉净油(Jasmin absolute)、甘松油(Jatamansi oil)、杜松籽油(Juniper berry oil)、杜松叶油、卡胡尔油(Kachur oil)、劳丹脂净油(Labdanumabsolute)、劳丹树脂型物(Labdanum resinoid)、熏衣草油(Lavender oil)、柠檬油、柠檬油萜、柠檬香茅草油(Lemongrass oil)、酸橙油(Lime oil)、山苍子油(Litsea cubebaoil)、山苍子萜(Litsea cubeba terpenes)、Lobhan choya树脂型物、橘油(Mandarinoil)、薄荷油(Mentha arvenis oil)、柠檬薄荷油(Mentha citrata oil)、含羞草净油(Mimosa absolute)、没药树脂型物(Myrrh resinoid)、莎草油(Nagarmotha oil)、肉豆蔻油(Nutmeg oil)、橡苔净油(Oakmoss absolute)、橡苔树脂型物(Oakmoss resinoid)、乳香油(Olibanum oil)、乳香树脂型物(Olibanum resinoid)、橙油、牛至油(Origanum oil)、玫瑰草油(Palma rosa oil)、广藿香油(Patchouli oil)、胡椒薄荷油(Peppermint oil)、秘鲁香脂树脂型物(Peru Balsam resinoid)、卑柠油(Petitgrain oil)、松叶油(Pineneedle oil)、粉椒油(Pink pepper oil)、玫瑰净油(Rose absolut)、玫瑰油(Rose oil)、迷迭香油、檀香木油(Sandalwood oil)、海藻净油(Seaweed absolute)、留兰香油(Spearmint oil)、印度苏刚达精油(Sugandh kokila oil)、印度苏刚达香薰油(Sugandhmantri oil)、万寿菊油(Tagete oil)、妥卢香脂树脂型物(Tolu Balsam resinoid)、晚香玉净油(Tuberose absolute)、姜黄油(Turmeric oil)、松节油(Turpentine oil)、缬草油(Valerian oil)、香根油(Vetiver oil)、香根萜(Vetiver terpenes)。
合成原料,例如:
酯类例如:C16醛、格蓬酯、己酸烯丙基酯、环己基丙酸烯丙基酯、庚酸烯丙基酯、苯氧基乙酸烯丙基酯、乙酸异戊酯、苯甲酸戊酯、丁酸戊酯、己酸戊酯、肉桂酸戊酯、异戊酸戊酯、苯基乙酸戊酯、丙酸戊酯、水杨酸异戊酯、乙酰化香树油(Amyris acetate)、乙酸茴香酯、乙酸苄酯、苯甲酸苄酯、丁酸苄酯、肉桂酸苄酯、甲酸苄酯、异丁酸苄酯、苄基异丁香酚、丙酸苄酯、水杨酸苄酯、惕各酸苄酯、乙酸丁酯、丁酸丁酯、丁酰乳酸丁酯、乙酸石竹烯酯(Caryophyllene acetate)、乙酸柏木酯(Cedryl acetate)、乙酸肉桂酯、丁酸肉桂酯、顺式-3-己烯基乙酸酯、顺式-3-己烯基苯甲酸酯、顺式-3-己烯基己酸酯、顺式-3-己烯基甲酸酯、顺式-3-己烯基异丁酸酯、顺式-3-己烯基-2-甲基丁酸酯、顺式-3-己烯基丙酸酯、顺式-3-己烯基水杨酸酯、顺式-3-己烯基惕各酸酯、乙酸香茅酯(Citronellyl acetate)、丁酸香茅酯、甲酸香茅酯、异丁酸香茅酯、丙酸香茅酯、惕各酸香茅酯、异丁酸三环癸烯酯(Cyclabute)、环格蓬酯(Cyclogalbanate)、环己基乙酸乙酯、乙酸癸酯、邻苯二甲酸二丁酯、丙二酸二乙酯、邻苯二甲酸二乙酯、乙酸二氢月桂烯酯(Dihydromyrcenyl acetate)、乙酸二甲基辛酯、乙酸二甲基苯基乙基原酯(Dimethyl phenyl ethyl carbinyl acetate)、己二酸二辛酯、邻苯二甲酸二辛酯、乙酸二甲基苄基原酯、丁酸二甲基苄基原酯、乙酸乙基芳樟酯(Ethyl linalyl acetate)、2-甲基丁酸乙酯、3-苯基丙酸乙酯、乙酸乙酯、乙酰乙酸乙酯、苯甲酸乙酯、丁酸乙酯、癸酸C10乙酯、己酸C6乙酯、辛酸C8乙酯、肉桂酸乙酯、庚酸乙酯、乙基己基乙酸酯、异丁酸乙酯、月桂酸乙酯、壬酸乙酯(Ethyl pelargonate)、苯氧基乙酸乙酯、乙基苯基乙酸酯、乙基苯基环氧乙烷甲酸酯(Ethyl phenyl glycidate)、丙酸乙酯、藏红花酸乙酯(Ethyl safranate)、水杨酸乙酯、戊酸乙酯、乙酸丁香酚酯(Eugenylacetate)、Evernyl、乙酸小茴香酯(Fenchyl acetate)、Floramat、Frescolat ML、乙酸乙基甲基二茂烷酯(Fructone)、三环癸烷羧酸乙酯(Fruitate)、乙酸香叶酯(Geranylacetate)、丁酸香叶酯、甲酸香叶酯、丙酸香叶酯、惕各酸香叶酯、2-乙基-6,6-二甲基-2-环己烯-1-甲酸乙酯(Givescone)、乙酸愈创木醇酯(Guaiol acetate)、二氢茉莉酮酸酯(Hedionate)、二氢茉莉酮酸甲酯(Hedione)、海菲麝香(Helvetolide)、香菠酯(Herbanate)、乙酸己酯、苯甲酸己酯、丁酸己酯、己酸己酯、异丁酸己酯、丙酸己酯、水杨酸己酯、乙酸异冰片酯、乙酸异丁酯、异丁基苯基乙酸酯、水杨酸异丁酯、乙酸异丁香酚酯(Isoeugenyl acetate)、乙酸异壬酯、异戊酸酯、2-甲基丁酸异丙酯、肉豆蔻酸异丙酯、茉莉酯(Jasmonyl)、顺式-3-己烯醇碳酸甲酯(Liffarome)、乙酸芳樟酯(Linalyl acetate)、藿檀酯(Mahagonate)、母菊酯(Manzanate)、二氢松香醇乙酸酯(Menthanyl acetate)、乙酸薄荷酯、苯甲酸甲酯、2-甲基丁基乙酸酯、2-甲基戊丁酯(Methyl camomille)、肉桂酸甲酯、环香叶酸甲酯(Methyl cyclogeranate)、庚炔羧酸甲酯(Methyl heptine carbonate)、月桂酸甲酯、辛炔羧酸甲酯(Methyl octine carbonate)、苯基乙酸甲酯、水杨酸甲酯、甲基-2-甲基丁酸酯、新福力酯(Neofolione)、乙酸诺吡酯(Nopyl acetate)、乙酸辛烯基酯、乙酸辛酯、异丁酸辛酯、乙酸对甲酚酯(Para cresyl acetate)、异丁酸对甲酚酯、苯基乙酸对甲酚酯、梨酯、2-甲基戊酸2-甲基戊酯(Peranat)、异丁酸苯氧基乙酯、乙酸苯基乙酯、丁酸苯基乙酯、甲酸苯基乙酯、异丁酸苯基乙酯、苯基乙酸苯基乙酯、丙酸苯基乙酯、水杨酸苯基乙酯、惕各酸苯基乙酯、异丁酸苯基丙酯、乙酸异戊二烯酯(Prenyl acetate)、罗曼麝香(Romandolide)、Sagecete、乙酸苏合香酯(Styrallyl acetate)、丙酸苏合香酯(Styrallylpropionate)、红桔酯(Tangerinol)、乙酸松油酯(Terpinyl acetate)、Thesaron、反式-2-己烯基乙酸酯、Tropicate、2-叔丁基环己基乙酸酯(Verdox)、乙酸三环癸烯酯(Verdylacetate)、丙酸三环癸烯酯、乙酸对叔丁基环已酯(Vertenex)、二甲基-3-苯丁醇乙酸酯(Vetikol acetate)、乙酸香根酯(Vetiveryl acetate)、Yasmolys。
内酯类,如:黄葵内酯(Ambrettolide)、Arova N、3-丙亚基-1-异苯并呋喃酮(Celeriax)、δ-癸内酯、γ-癸内酯、δ-十二内酯、γ-十二内酯、巴西酸亚乙酯(Ethylenebrassylate)、环十五内酯(Exaltolide)、γ-庚内酯、δ-己内酯、γ-己内酯、甲基莱托酮(Methyl laitone)、甲基辛内酯、δ-壬内酯、γ-壬内酯、八氢香豆素、δ-辛内酯、γ-辛内酯、Rootylone、环十六内酯(Silvanone supra)、δ-十一内酯、γ-十一内酯、γ-戊内酯、10-氧杂十六内酯(OHD麝香)、香豆素(Coumarin)、环十五烯内酯(Habanolide)、茉莉内酯(Jasmolactone)。
醛类,如:乙醛、阿道克醛(Adoxal)、C10醛、异C11醛(Aldehyde C11 iso)、C11 moa醛、十一碳烯醛C11 (Aldehyde C11 undecylenic)、十一碳醛C11 (Aldehyde C11undecylic)、月桂醛C12、醛C12 MNA、茴香醛(Anisaldehyde)、戊基肉桂醛、苯甲醛、波洁红醛(Bourgeonal)、樟脑烯醛(Campholenaldehyde)、Cantonal、紫罗兰醛(Cetonal)、肉桂醛、顺式-4-癸烯醛、顺式-6-壬烯醛、柠檬醛、香茅醛、香茅基氧基乙醛(Citronellyloxyacetaldehyde)、可卡醛(Cocal)、枯茗醛(Cuminaldehyde)、Curgix、Cyclal C、兔耳草醛(Cyclamen aldehyde)、铃兰甲醛(Cyclomyral)、女贞醛(Cyclovertal)、癸烯醛-9、Dupical、柑青醛(Empetal)、乙基香草醛(Ethyl vanillin)、海风醛(Floralozone)、花青醛(Florhydral)、癸二烯醛(Geraldehyde)、胡椒基丙醛(Helional)、洋茉莉醛(Heliotropin)、庚醛、己醛、己基肉桂醛、新铃兰醛(Hivernal neo)、氢化阿托醛(Hydratropaldehyde)、羟基香茅醛、内十一烯醛(Intreleven aldehyde)、异丁酸香兰酯(Isobutavan)、异环柠檬醛(Isocyclocitral)、异戊醛、铃兰醛(Lilial)、新柠檬醛(Limonenal)、马赛醛(Maceal)、梅弗兰醛(Mefranal)、甜瓜醛(Melonal)、甲基肉桂醛、反式,顺式-2,6-壬二烯醛、壬醛、辛醛、Oncidal、对甲苯醛(Para tolyl aldehyde)、苯基乙醛、苯基丙醛、甲基柑青醛B (Precyclemone B)、藏红花醛(Safranal)、水杨醛、清风醛(Scentenal)、丁香醛(Syringa aldehyde)、反式-4-癸烯醛、反式-2-十二烯醛、反式-2-己烯醛、反式-2-壬醛、新女贞醛(Trifernal)、香草醛、藜芦醛(Veratraldehyde)、鲜草醛(Vernaldehyde)。
酮类,如:山楂花酮(Acetanisol)、乙偶姻(Acetoin)、苯乙酮、Aldron、烯丙基紫罗兰酮(Allyl ionone)、苯甲酮、苄基丙酮、西瓜酮(Calone)、莰酮(Camphor)、d-香芹酮、l-香芹酮、喀什米尔木麝香(Cashmeran)、柏木基甲基酮(Cedryl methyl ketone)、二氢茉莉酮酸甲酯(Cepionate)、Claritone、Cosmone、萨利麝香(Crysolide)、Cyclotene、大马烯酮(Damascenone)、大马酮α、大马酮β、大马酮δ、大马酮γ、二乙酰(Diacetyl)、二氢-β-紫罗兰酮、二氢茉莉酮酸酯(Dihydro isojasmonate)、二甲基辛烯酮、王朝酮(Dynascone)、乙基戊基酮、乙基麦芽酚、葑酮(Fenchone)、榛子酮(Filbertone)、香叶基丙酮(Geranylacetone)、环十六烯酮(Globanone)、庚基环戊酮、己基环戊酮、α-紫罗兰酮(Ionone α)、β-紫罗兰酮、紫罗兰酮纯(Ionone pure)、鸢尾木(Iriswood)、α-鸢尾酮(Irone α)、龙涎酮(Iso E Super)、异葑酮(Isofenchone)、异茉莉酮T (Isojasmone T)、异洛酮K (IsoloneK)、异薄荷酮(Isomenthone)、异佛尔酮、顺式-茉莉酮(Jasmone cis-)、Kambernoir、加菲力士(Kephalis)、6-五甲基庚-3-烯-2-酮(Koavone)、Lavendinal、麦芽酚(Maltol)、薄荷酮、甲基苯乙酮、甲基戊基酮、甲基庚烯酮、甲基己基酮、γ-甲基紫罗兰酮、甲基萘基酮β、甲基壬基酮、麝香烯酮(Muscenone)、麝香酮(Muscone)、桃酮(Nectaryl)、Orinox、OTBC酮、对叔丁基环己酮、Patchwood、粉檀麝香(Phantolid)、Pharaone、胡椒酮(Piperitone)、普利卡酮(Plicatone)、覆盆子酮(Raspberry ketone)、覆盆子酮甲基醚、藏花茚(Safraleine)、螺环格蓬酮纯(Spirogalbanone pure)、吐纳麝香(Tonalid)、三甲基琥珀酮(Trimofix O)、凡路酮(Veloutone)、Vetikon。
醇类,如:羰基合成C13醇(Alcohol oxo C13)、琥珀核(Amber core)、Ambermax、龙涎香八氢萘醇(Ambrinol)、戊基乙烯基原醇(Amyl vinyl carbinol)、茴香醇(Anisicalcohol)、白檀醇(Bacdanol)、苄醇、丁醇、结晶柏木醇(Cedrol crystals)、肉桂醇、香茅醇、花冠醇(Coranol)、癸醇(Decanol)、二甲基苄基原醇、二甲基辛醇、二甲基苯基乙基原醇、二甲基庚醇(Dimetol)、葑醇(Fenchol)、己醇、异冰片(Isoborneol)、异冰片基环己醇、爪哇檀香(Javanol)、Keflorol、四甲基-4-亚甲基-2-庚醇(Kohinool)、月桂醇、Lilyflore、氧化芳樟醇(Linalool oxide)、五月铃兰醇(Mayol)、薄荷醇、赛木香醇(Norlimbanol)、辛醇、沙针醇(Osyrol)、对叔丁基环己醇、苯基异己醇(Phenoxanol)、苯氧基乙醇、苯基乙醇、苯基丙醇、丙二醇、甲基苯戊醇(Rosaphen)、玫瑰二醇、苏合香醇(Styrallyl alcohol)、三环癸烷二甲醇、四氢芳樟醇、四氢月桂烯醇、特木倍醇(Timberol)、甲基癸烯醇(Undecavertol)、顺式-3-己烯醇、左旋香茅醇(Citronellol laevo)、环花醇(Cyclofloranol)、二氢芳樟醇(Dihydrolinalool)、二氢月桂烯醇(Dihydromyrcenol)、二氢月桂烯醇(Dimyrcetol)、黑檀醇(Ebanol)、香叶醇(Geraniol)、异蒲勒醇(Isopulegol)、里哪醇(Linalool)、橙花醇(Nerol)、橙花叔醇(Nerolidol)、反式,顺式-2,6-壬二烯醇、聚檀香醇(Polysantol)、Rosalva、白雷曼檀香核(Sandalmysore core)、檀香(Sandalore)、萜烯-4-醇(Terpinen-4-ol)、萜品醇(Terpineol)、反式-2-己烯醇。
酚类,如:丁羟茴醚、二氢丁香酚(Dihydroeugenol)、丁香酚纯(Eugenol pure)、愈创木酚、异丁香酚、间甲酚、甲基丹提力士(Methyl diantilis)、对甲酚、丙烯基乙基愈创木酚(Propenyl guaethol)、麝香草酚(Thymol)、香荚兰醇(Ultravanil)。
醚类,如:降龙涎香醚(Ambroxan)、茴香脑(Anethole)、花药(Anther)、苄基异戊基醚、苄基异丙基醚、异戊酸苄酯、鸢尾香木(Boisiris)、柏木甲醚(Cedramber)、降龙涎醚(Cetalox)、癸基甲基醚、二苄基醚、二氢玫瑰氧化物、二甲氢醌、二甲间苯二酚、二苯醚(Diphenyl oxide)、道立米(Doremox)、草蒿脑(Estragole)、乙基芳樟醇、桉油精、佳乐麝香(Galaxolide)、吉兰吡喃(Gyrane)、Herbavert、酸橙氧化物(Lime oxide)、Madrox、甲基异丁香酚、萘基异丁基醚β、橙花醚(Nerol oxide)、萘乙醚(Nerolin bromelia)、对甲苯基丁醚、对甲苯基甲基醚、Petiole、苯基乙基甲基醚、2,4-二甲基-4-苯基呋喃(Rhubafuran)、玫瑰氧化物(Rose oxide)、芳香玫瑰醚(Rosyrane)、龙涎香醚(Trisamber)、Vetylbois K、萘基甲基醚(Yara yara)。
缩醛如:乙缩醛CD、乙缩醛R、龙涎缩醛(Amberketal)、乙氧基环十二烷基甲烷(Boisambrene forte)、柠檬醛二乙缩醛(Citrathal)、1,1-二乙氧基乙烷、翠绿亚胺(Emeraldine)、Freshopal、薰衣草噁烷(Herboxane)、Indoflor、Jacinthaflor、Magnolan、香辣醚(Spirambrene)、苯乙醛二甲缩醛(Viridine)、爱林塔尔(Elintaal)、克力二噁茂烷(Glycolierral)、卡拉花醛(Karanal)、圆柚甲烷(Methyl pamplemousse)。
烃类,如:红没药烯(Bisabolene)、莰烯、蒈烯δ3 (Carene delta 3)、石竹烯(Caryophyllene)、柏木烯(Cedrene)、对伞花烃(Cymene para)、二戊烯(Dipentene)、二苯基甲烷、异长叶烯(Isolongifolene)、d-柠檬烯、长叶烯(Longifolene)、月桂烯(Myrcene)、萘、罗勒烯(Ocimene)、水芹烯α、蒎烯α、蒎烯β、苯乙烯、萜品烯γ、萜品油烯(Terpinolene)、1,3,5-十一碳三烯、异丙基格篷(Verdoracine)。
硫化合物,如:主体黑醋栗(Corps cassis)、二丁基硫醚、二甲基硫醚、2-己基-3-氧代环戊羧酸甲酯(Exovert)、西柚硫醇(Grapefruit thiol)、噁烷(Oxane)、巯基马来酮(Ribes mercaptan)、硫噻唑(Sulfurol)、桉叶硫醚(Thiocineol)。
腈类,如:肉桂腈(Cinnamyl nitrile)、香茅腈(Citronellyl nitrile)、3,7-二甲基-6-辛烯腈(Citronitrile)、Clonal、枯茗腈(Cumin nitrile)、鸢尾腈、3,7-二甲基-2,6-辛二烯腈(Lemonile)、牡丹腈(Peonile)、十三烷基腈、Agrumen nitrile、癸腈。
肟类,如:二甲基二环辛酮肟(Buccoxime)、雷冰诺星(Labienoxime)、榄青酮(Stemone)。
氮杂环,如:2-乙酰吡嗪、2-乙酰吡啶、仲丁基喹啉、Corps racine、2-乙基-3,5(或6)-二甲基吡嗪、糠基吡咯、吲哚、异丁基喹啉、2-异丁基-3(或6)-甲氧基吡嗪、异丙基喹啉、Maritima、对甲基喹啉、3-甲基吲哚(Skatol)、2,3,5-三甲基吡嗪。
硝基化合物如:麝香酮(Musk Ketone)。
希夫碱类,如:橙花素(Aurantiol)、半日花素(Helianthral)、女贞缩醛(Ligantraal)、玲兰素(Verdantiol)。
其它材料如:乙酰苯胺、环胺(Gardamide)、对苯二甲酰胺、邻氨基苯甲酸二甲基酯、邻氨基苯甲酸甲酯、正丁酸、癸酸、己酸、辛酸、苯基乙酸、石竹烯氧化物、环氧柏木醚(Cedroxyde)、Tobacarol。
因此,式(1)、式(2)、式(3)或式(4)的化合物可用于生产组合物,和如从上述汇编中可以明显看出的,可用于生产广泛的已知气味剂/香味、风味和/或除臭/掩蔽材料。在这样的组合物的生产中,早先提及的已知的香味、风味和/或除臭/掩蔽材料可以根据香料商已知的方法使用,例如,根据W. A. Poucher, Perfumes, Cosmetics and Soaps 2, 第7版, Chapman and Hall, 伦敦1974。
在本发明的一个实施方式中,所要求保护的香味、风味和/或除臭/掩蔽组合物除了包含式(1)或式(2)或式(3)或式(4)的缩醛之外,还包含至少一种酯和/或一种醇,优选至少酯和醇的混合物;所述酯和/或醇优选选自本文上面所定义的列表。在本发明的一个实施方式中,要求保护的气味剂组合物的特征在于式(1)或式(2)或式(3)或式(4)的化合物与所述酯和/或醇的总含量大于25重量%,优选大于50重量%,例如大于75重量%,或甚至大于90重量%。
在本发明的另一个实施方式中,所要求保护的香味、风味和/或除臭/掩蔽组合物除了包含式(1)或式(2)或式(3)或式(4)的缩醛之外,还包含它们各自的式(5)或式(6)或式(7)或式(8)的母体酚。在本发明的一个实施方式中,要求保护的气味剂组合物的特征在于式(1)或式(2)或式(3)或式(4)的化合物与它们各自的式(5)或式(6)或式(7)或式(8)的母体酚的总含量大于5重量%,例如大于25重量%,优选大于50重量%,例如大于75重量%,或甚至大于90重量%。
在本发明的另一个实施方式中,在要求保护的香味、风味和/或除臭/掩蔽组合物中,式(1)或式(2)或式(3)或式(4)的缩醛与它们各自的式(5)或式(6)或式(7)或式(8)的母体酚之间的重量比为0.01/99.99至99.99/0.01,例如0.1/99.9至99.9/0.1,例如1/99至99/1,例如1/99至20/80。在本发明的另一个实施方式中,在要求保护的香味、风味和/或除臭/掩蔽组合物中,式(1)或式(2)或式(3)或式(4)的缩醛与它们各自的式(5)或式(6)或式(7)或式(8)的母体酚之间的重量比为80/20至99/1。
在本发明的另一个实施方式中,所要求保护的香味、风味和/或除臭/掩蔽组合物除了包含通过使相应的式(5)或式(6)或式(7)或式(8)的母体酚与乙氧基乙烯反应而制备的式(1)或式(2)或式(3)或式(4)的缩醛之外,还包含在母体酚和乙氧基乙烯的所述反应步骤期间获得的至少一种副产物。
制备
在本发明的一个优选的实施方式中,式(1)、式(2)、式(3)或式(4)的化合物可以有利地通过分别使2-乙氧基-4-甲基苯酚(5);3-乙氧基-4-(1-乙氧基乙氧基)苯甲醛(6);2-乙氧基-4-(4-甲基-1,3-二氧戊环-2-基)苯酚(7);和2-乙氧基-4-(甲氧基甲基)苯酚(8)与乙氧基乙烯在酸性条件下反应而制备。
警示:乙氧基乙烷会与酸剧烈反应,当向反应混合物中加入酸催化剂时必须小心。低效冷却或盐酸过量可导致热超限。
实施例1
合成2-乙氧基-1-(1-乙氧基乙氧基)-4-甲基苯。
在0℃下,在分子氮下,在搅拌下,将37%盐酸(40μl,465 μmol)加入到2-乙氧基-4-甲基苯酚(17.0g,112 mmol)和乙氧基乙烯(13.4 mL,140 mmol)的混合物中。将混合物搅拌2小时,在20℃下放置过夜。随后加入碳酸钠(106 mg,1 mmol),减压除去挥发物。使用Kugelrohr装置(100℃/1毫巴)真空蒸馏粗产物,得到2-乙氧基-1-(1-乙氧基乙氧基)-4-甲基苯(20.3g,81%),为无色液体。
1H NMR (500 MHz, DMSO-d6) δ 6.89 (d,J = 8.0 Hz,1H),6.81 (d,J = 1.8Hz,1H),6.65 (dd,J = 8.0,1.3 Hz,1H),5.20 (q,J = 5.2 Hz,1H),4.00 (q,J = 7.0 Hz,2H),3.81 – 3.72 (m,1H),3.56 – 3.47 (m,1H),2.24 (s,3H),1.35 (d,J = 5.2 Hz,3H),1.33 (t,J = 7.0 Hz,3H),1.10 (t,J = 7.1 Hz,3H)。
13C NMR (125 MHz,DMSO-d6) δ= 150.38,143.91,132.86,121.34,120.72,115.05,101.50,64.07,62.05,21.14,20.99,15.56,151.19。
实施例2
合成3-乙氧基-4-(1-乙氧基乙氧基)苯甲醛。
在分子氮下,在搅拌下,将37%盐酸(200μL,2.33 mmol)加入到3-乙氧基-4-羟基苯甲醛(40.0g,241 mmol)、乙氧基乙烯(13.4 mL,301 mmol)和二氯甲烷(50 mL)的混合物中。将混合物搅拌2小时,在20℃下静置三天。随后加入乙氧基乙烯(2.30 mL,24 mmol)、37%盐酸(20μL,233μmol),并将混合物静置过夜。然后加入碳酸钠(950 mg,9 mmol),并减压除去挥发物。使用Kugelrohr装置(146℃,1毫巴)真空蒸馏残余物,得到3-乙氧基-4-(1-乙氧基乙氧基)苯甲醛(47.0g,78%),为灰白色固体。
1H NMR (500 MHz,DMSO-d6) δ 9.85 (s,1H),7.50 (dd,J = 8.2,1.9 Hz,1H),7.44 (d,J = 1.9 Hz,1H),7.25 (d,J = 8.2 Hz,1H),5.56 (q,J = 5.2 Hz,1H),4.11 (q,J = 7.0 Hz,2H),3.75 – 3.67 (m,1H),3.56 – 3.47 (m,1H),1.44 (d,J = 5.2 Hz,3H),1.36 (t,J = 7.0 Hz,3H),1.11 (t,J = 7.1 Hz,3H)。
13C NMR (126 MHz,DMSO-d6) δ 191.51,151.49,149.54,130.73,124.95,117.09,111.93,100.31,63.93,61.60,20.21,15.02,14.54。
实施例3
合成2-(3-乙氧基-4-(1-乙氧基乙氧基)苯基)-4-甲基-1,3-二氧戊环。
在分子氮下,在搅拌下,将37%盐酸(56μL,651μmol)加入到2-乙氧基-4-(4-甲基-1,3-二氧戊环-2-基)苯酚(37.7g,168 mmol)与乙氧基乙烯(21.3 mL,223 mmol)的混合物中。将反应混合物搅拌2小时,在20℃下放置三天。随后加入碳酸钠(1.06g,10 mmol),并在减压下除去挥发物。使用Kugelrohr装置(165℃,1毫巴)真空蒸馏残余物,得到2-(3-乙氧基-4-(1-乙氧基乙氧基)苯基)-4-甲基-1,3-二氧戊环(20.8g,42%,非对映异构体比例44:56),为无色液体。
1H NMR (500 MHz,DMSO) δ 7.04 – 6.99 (m,2H),6.94 (dd,J = 8.2,1.9 Hz,0.56H),6.92 (dd,J = 8.2,1.9 Hz,0.44H),5.79 (s,0.44H),5.66 (s,0.56H),5.34 –5.27 (m,1H),4.34 – 4.20 (m,1.44H),4.06 – 3.99 (m,2.56H),3.78 – 3.70 (m,1H),3.55 – 3.47 (m,1.56H),3.45 (dd,J = 7.9,7.0 Hz,0.44H),1.37 (dd,J = 5.2,2.1 Hz,3H),1.33 (td,J = 7.0,2.1 Hz,3H),1.28 (d,J = 6.1 Hz,1.68H),1.24 (d,J = 6.1 Hz,1.32H),1.10 (td,J = 7.0,0.9 Hz,3H)。
13C NMR (126 MHz,DMSO-d6) δ 149.63,149.59,146.42,146.28,133.26,132.78,119.12,118.93,112.02,111.75,102.90,101.84,100.77,72.61,71.70,71.28,70.59,63.80,61.51,20.44,18.53,18.31,15.07,14.66。
实施例4
合成2-乙氧基-1-(1-乙氧基乙氧基)-4-(甲氧基甲基)苯。
在分子氮下,在搅拌下,将37%盐酸(7μL,81μmol)加入到2-乙氧基-4-(甲氧基甲基)苯酚(4.00g,22 mmol)和乙氧基乙烯(2.63 mL,27.5 mmol)的混合物中。将反应混合物搅拌2小时,在20℃下放置三天。随后加入碳酸钠(106 mg,1 mmol),并在减压下除去挥发物。使用Kugelrohr装置(260℃/6毫巴)真空蒸馏残余物,得到2-乙氧基-1-(1-乙氧基乙氧基)-4-(甲氧基甲基)苯(4.16g,74%),为无色液体。
1H NMR (500 MHz,DMSO-d6) δ 6.98 (d,J = 8.1 Hz,1H),6.93 (d,J = 1.9 Hz,1H),6.80 (dd,J = 8.1,1.9 Hz,1H),5.27 (q,J = 5.2 Hz,1H),4.32 (s,2H),4.02 (q,J= 7.0 Hz,2H),3.79 – 3.71 (m,1H),3.55 – 3.47 (m,1H),3.26 (s,3H),1.36 (d,J =5.2 Hz,3H),1.33 (t,J = 7.0 Hz,3H),1.10 (t,J = 7.1 Hz,3H)。
13C NMR (126 MHz,DMSO-d6) δ 149.79,145.04,133.12,119.90,119.55,113.15,100.83,73.42,63.68,61.52,57.30,20.48,15.08,14.68。
组合物实施例
在以下发明中,将各实施例(B/C/D)包括在用于皂的麝香调协香味中(A =空白)。
不同化合物的比较研究,其中A栏是空白:
引入0.2重量%的2-乙氧基-1-(1-乙氧基乙氧基)-4-甲基苯(化合物(1))提供具有如麝香酊剂中观察到的甜味和天然动物方面的麝香调协。这种效果随着时间进一步发展。(C)·2-乙氧基-1-(1-乙氧基乙氧基)-4-甲基苯(1)显示显著的光稳定性。
与两种其它香草材料相比,观察到以下效果:
引入0.5重量%的乙基香草醛产生更甜的麝香效果,更"粉状"香调;肥皂随时间向浅棕色变色(D)。
引入0.2重量%的香荚兰醇产生强烈的酚效果,将麝香香调变成刺鼻的动物气味。随着时间的推移,皂发生非常轻微的变色(B)。
在以下发明中,将各实施例(B/C/D)包括在用于皂的香辛料调协香味中(A =空白)。
不同化合物的比较研究,其中A栏是空白:
引入0.2重量%的2-乙氧基-1-(1-乙氧基乙氧基)-4-甲基苯(化合物(1))提供具有类似天然香草豆的强烈温暖甜味方面的香辛料调协。这种效果随着时间进一步发展。(C) 2-乙氧基-1-(1-乙氧基乙氧基)-4-甲基苯显示显著的光稳定性。
与两种其它香草材料相比,观察到以下效果:
引入0.5重量%的乙基香草醛产生合成的干香草效果;肥皂随时间向浅棕色变色(D)。
引入0.2重量%的香荚兰醇产生强的酚效果;随着时间的推移,皂发生非常轻微的变色(B)。
Claims (18)
2.根据权利要求1所述的香味、风味和/或除臭/掩蔽组合物,其中所述缩醛选自化合物(1)、化合物(3)和化合物(4)。
3.根据前述权利要求中任一项所述的香味、风味和/或除臭/掩蔽组合物,其中所述缩醛化合物的含量为0.0001-95重量%。
4.根据权利要求3所述的香味、风味和/或除臭/掩蔽组合物,其中所述缩醛化合物的含量为0.1-10重量%。
5.根据前述权利要求中任一项所述的香味、风味和/或除臭/掩蔽组合物,其中所述组合物还包含至少一种酯和/或一种醇。
6.根据权利要求5所述的香味、风味和/或除臭/掩蔽组合物,其中式(1)或式(2)或式(3)或式(4)的化合物与所述酯和/或醇的总含量大于25重量%。
8.根据权利要求7所述的香味、风味和/或除臭/掩蔽组合物,其中式(1)或式(2)或式(3)或式(4)的化合物与它们各自的式(5)或式(6)或式(7)或式(8)的母体酚的总含量大于5重量%。
9.根据权利要求7或8中任一项所述的香味、风味和/或除臭/掩蔽组合物,其中式(1)或式(2)或式(3)或式(4)的缩醛与它们各自的式(5)或式(6)或式(7)或式(8)的母体酚之间的重量比为0.01/99.99至99.99/0.01,例如0.1/99.9至99.9/0.1,例如1/99至99/1,例如1/99至20/80。
10.根据权利要求7或8中任一项所述的香味、风味和/或除臭/掩蔽组合物,其中式(1)或式(2)或式(3)或式(4)的缩醛与它们各自的式(5)或式(6)或式(7)或式(8)的母体酚之间的重量比为80/20-99/1。
11.根据前述权利要求中任一项所述的香味、风味和/或除臭/掩蔽组合物,其中除了式(1)或式(2)或式(3)或式(4)的缩醛之外,所述组合物还包含各自的式(5)或式(6)或式(7)或式(8)的母体酚与乙氧基乙烯之间的反应的反应产物。
13.根据权利要求12所述的缩醛,其中所述缩醛选自化合物(1)、化合物(3)和化合物(4)。
14.根据权利要求1-11中任一项所述的香味、风味和/或除臭/掩蔽组合物在加香或调味产品中的用途。
15.根据权利要求12-13中任一项所述的缩醛在加香或调味产品中的用途。
17.根据权利要求16所述的制备缩醛的方法,其中所述合成通过使式(5)、(6)、(7)或(8)的化合物与乙氧基乙烯反应来进行。
18.根据权利要求17所述的制备缩醛的方法,其中所述合成在酸性条件下进行。
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US (1) | US11661565B2 (zh) |
EP (1) | EP3728532B1 (zh) |
JP (1) | JP7232833B2 (zh) |
CN (1) | CN111770980A (zh) |
BR (1) | BR112020012259A2 (zh) |
ES (1) | ES2901632T3 (zh) |
MX (1) | MX2020006683A (zh) |
WO (1) | WO2019121032A1 (zh) |
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US3636158A (en) * | 1969-06-23 | 1972-01-18 | Merck & Co Inc | 3-methoxy-benzaldehydes |
US4383943A (en) * | 1981-10-07 | 1983-05-17 | Fritzsche Dodge & Olcott Inc. | Acetaldehyde ethyl isoeugenyl acetal perfume compositions |
US20060034992A1 (en) * | 2002-11-28 | 2006-02-16 | Nelissen Jean P | Flavor and fragrance compounds |
CN103781890A (zh) * | 2011-09-12 | 2014-05-07 | 弗门尼舍有限公司 | 加香缩醛 |
US20160333291A1 (en) * | 2014-01-16 | 2016-11-17 | Takasago International Corporation | Fragrance composition |
Family Cites Families (8)
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JPS57188537A (en) * | 1981-05-13 | 1982-11-19 | T Hasegawa Co Ltd | Substituted benzaldehyde acetals, their preparations, and uses |
US4473588A (en) | 1983-06-16 | 1984-09-25 | International Flavors & Fragrances Inc. | Flavoring with 2-methoxy-4-(2-methylpropenyl) phenyl ester of isobutyric acid |
JP3708129B2 (ja) | 1996-03-22 | 2005-10-19 | ザ プロクター アンド ギャンブル カンパニー | 洗剤組成物およびフレグランス前駆体の分配のための使用法 |
DE19714826A1 (de) * | 1997-04-10 | 1998-10-15 | Haarmann & Reimer Gmbh | Ethylvanillinisobutyrat |
EP1705171A1 (en) * | 2001-12-19 | 2006-09-27 | Flexitral, Inc. | Improved aromachemicals |
BRPI0906523B1 (pt) * | 2008-01-22 | 2017-04-11 | Givaudan Sa | produto com sabor característico de baunilha recebido por via oral, método para conferir sabor ao mesmo, e compostos |
BR112012024827B1 (pt) | 2010-04-21 | 2020-12-15 | Firmenich Sa | Carbonatos orgânicos com aroma de baunilha |
JP6404266B2 (ja) * | 2016-05-27 | 2018-10-10 | 山本香料株式会社 | 臭気変調剤及び臭気変調方法 |
-
2018
- 2018-12-06 ES ES18811296T patent/ES2901632T3/es active Active
- 2018-12-06 MX MX2020006683A patent/MX2020006683A/es unknown
- 2018-12-06 JP JP2020534901A patent/JP7232833B2/ja active Active
- 2018-12-06 WO PCT/EP2018/083753 patent/WO2019121032A1/en unknown
- 2018-12-06 CN CN201880082296.2A patent/CN111770980A/zh active Pending
- 2018-12-06 EP EP18811296.5A patent/EP3728532B1/en active Active
- 2018-12-06 US US15/733,266 patent/US11661565B2/en active Active
- 2018-12-06 BR BR112020012259-9A patent/BR112020012259A2/pt unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US3636158A (en) * | 1969-06-23 | 1972-01-18 | Merck & Co Inc | 3-methoxy-benzaldehydes |
US4383943A (en) * | 1981-10-07 | 1983-05-17 | Fritzsche Dodge & Olcott Inc. | Acetaldehyde ethyl isoeugenyl acetal perfume compositions |
US20060034992A1 (en) * | 2002-11-28 | 2006-02-16 | Nelissen Jean P | Flavor and fragrance compounds |
CN103781890A (zh) * | 2011-09-12 | 2014-05-07 | 弗门尼舍有限公司 | 加香缩醛 |
US20160333291A1 (en) * | 2014-01-16 | 2016-11-17 | Takasago International Corporation | Fragrance composition |
Also Published As
Publication number | Publication date |
---|---|
EP3728532A1 (en) | 2020-10-28 |
JP7232833B2 (ja) | 2023-03-03 |
US20200399560A1 (en) | 2020-12-24 |
JP2021508351A (ja) | 2021-03-04 |
EP3728532B1 (en) | 2021-11-10 |
MX2020006683A (es) | 2020-09-03 |
US11661565B2 (en) | 2023-05-30 |
WO2019121032A1 (en) | 2019-06-27 |
ES2901632T3 (es) | 2022-03-23 |
BR112020012259A2 (pt) | 2020-11-24 |
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