CN105595296A - 含有噻喃-甲醛的风味和香味组合物 - Google Patents
含有噻喃-甲醛的风味和香味组合物 Download PDFInfo
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Abstract
本发明涉及一种新型的风味和香味组合物,其包含2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛。
Description
发明领域
本发明涉及一种新化学实体作为风味和香味材料的引入和用途。
发明背景
在风味工业中对于增强食物制品的新风味或是向食物制品提供新风味的风味化学品存在持续需求。对于香味化学品存在类似的持续需求,以便让调香师和其他人能够创造用于香精、古龙水和个人护理产品的新的香味。本领域技术人员了解分子的化学结构上的差异如何导致气味、香调(notes)和特性上的显著差异。对于新化学品结构变化的认定和发现使得能够发展新的风味和香味。
人们早已知道,硫化合物可能具有令人反感的气味,导致食品中的异味并造成空气污染(参见,BBadings,H.T.etal.Z.Lebensm.Unters.-Forsch.1976,161,pages53-59;Schaefer,J.Comm.Eur.Communities1980,第513-535页)。硫化合物,例如在鸡粪中观察到。在产蛋鸡舍的空气中也检测到这样的一种化合物2,6-二甲基-5,6-二氢-2H-噻喃-3-甲醛,并且其被确定为在鸡粪和产蛋鸡舍二者的气味中起重要作用(参见Schaefer,J)。在一个针对在食品制备或储藏期间硫化合物的形成的研究中,提出并研究了测试硫化氢和2-丁烯醛反应的模型体系。确定了许多硫化合物并报告了其异味(off-odor)性质。2,6-二甲基-5,6-二氢-2H-噻喃-3-甲醛被再次发现并描述为具有洋葱和金属气味。在该模型中,提出更多硫化合物,包括2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛。然而,没有分离和/或确认任何一种上述提出的分子,并且没有进行气味评估(参见,Badings,H.T.etal.;Kleipool,R.J.C.etal.Z.Lebensm.Unters.-Forsch.1976,161,第231-238页)。
现已发现,出乎意料并且与可能预期的相反,2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛具有令人惊讶的强烈的水果和热带气息的感官香调(tropicalorganolepticnotes),并因此在增强食品、口香糖、牙科产品、口腔卫生产品和医药产品的风味方面是特别有用的。
发明概述
本发明涉及通过添加嗅觉可接受量的如下所示的由式I表示的2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛来改善、增强或改性风味或香味组合物的方法:
本发明的另一个实施方式涉及包含2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛的风味或香味组合物。
本发明的另一个实施方式涉及一种组合物,其包含2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛和选自食品、口香糖、牙科产品、口腔卫生产品、医药产品、香精、古龙水、花露水、化妆品、个人护理产品、织物护理产品、清洁产品和空气清新剂的材料。
本发明的这些和其它实施方式将通过下面的描述而变得显而易见。
发明详述
可以用3-(乙酰硫基)-己醛制备本发明的2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛。其制备方法详述于下面的实施例I中。材料购自AldrichChemicalCompany,除非另有说明。
本领域技术人员将认识到,本发明的化合物含有手性中心,从而提供要求保护的化合物的多个异构体。在本文中意味着本发明的化合物包括异构体混合物以及使用本领域技术人员已知的技术可以分离的各个异构体。合适的技术包括色谱如高效液相色谱(称为HPLC,特别是硅胶色谱)和气相色谱捕集(称为GC捕集)。然而,这样产品的市售品大多以混合物提供。
发现2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛具有出乎意料的强烈且持久的水果和热带气息的香调(tropicalnotes),其通过提供风味增强和优选的整体的风味感觉在用于增加或向食品、口香糖、牙科和口腔卫生产品以及医药产品赋予味道增强(tasteenhancement)或体感效果(somatosensoryeffect)方面显示为有利的。本发明还涉及通过添加2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛而增加或向食品、口香糖、牙科和口腔卫生产品以及医药产品赋予味道增强或体感效果的方法。
当2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛用于风味组合物时,其可以与本领域公知的并且在以往已经广泛描述的常规调味材料或佐剂组合。常规的调味材料包括饱和脂肪酸,不饱和脂肪酸,氨基酸;醇,包括伯醇和仲醇;酯;包括酮的羰基化合物;醛;内酯;包括苯衍生物的环状有机材料;无环化合物;杂环化合物如呋喃,吡啶和吡嗪等;其它含硫化合物,包括硫醇、硫化物和二硫化物等;蛋白质;类脂;碳水化合物;所谓的风味增强剂如味精、谷氨酸镁、谷氨酸钙、乌苷酸和肌苷酸;天然调味材料如水解物、可可、香草和焦糖;精油和提取物,如茴香油和丁香油等;以及人工调味材料,如香兰素和乙基香兰素等。对于佐剂的要求包括:(1)它们对2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛不具反应性;(2)它们与2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛是感官兼容的,由此向其中添加有2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛的最终消费品的风味不会由于佐剂的使用而受到不利的影响;以及(3)它们是可摄取可接受的,因而是无毒或者要不然是非有害性的。此外,还可以包括其它风味材料、载体、稳定剂、增稠剂、表面活性剂、调理剂(conditioner)和风味增强剂。
2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛的用途还适用于当前的加香产品,包括香精与古龙水的制备、个人护理产品如肥皂、沐浴露和护发产品、织物护理产品以及空气清新剂和化妆品制剂的加香。本发明还可用于加香清洁剂,例如但不限于洗涤剂、洗碗剂(dishwashingmaterials)、去污组合物(scrubbingcompositions)和窗户清洁剂等等。
在这些制剂中,2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛可以单独使用或与其它加香组合物、溶剂和佐剂等组合使用。也可使用的其它成分的性质与种类是本领域技术人员已知的。多种香料可用于本发明,唯一的限制是其与所使用的其它组分的相容性。合适的香料包括但不限于果香如杏仁、苹果、樱桃、葡萄、梨、菠萝、橙子、草莓、覆盆子;麝香;花香如类薰衣草、类玫瑰、类鸢尾、类康乃馨。其它令人愉悦的气味包括衍生自松树、云杉和其它林木气味的草药和林地气味。香料还可以衍生自各种油,如精油(essentialoils),或衍生自植物材料如薄荷和留兰香等。
在美国专利号4,534,891中提供了合适的香料的列表,其列举的内容在此经全文引用并入本文中。合适的香料的另一来源可以在W.A.Poucher编辑的Perfumes,CosmeticsandSoaps,第二版,1959中找到。该论文中提供的香料是刺槐、金合欢、素心兰、仙客来、蕨、栀子、山楂、天芥菜、金银花、风信子、茉莉、丁香、百合、玉兰花、含羞草、水仙、新鲜切割的干草、橙花、兰花、木犀草、香豌豆、三叶草、晚香玉、香草、紫罗兰和桂竹等等。
2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛可以与补充(complementary)香味化合物组合使用。如本文所用,术语“补充香味化合物”定义为选自以下的香味化合物:2-[(4-甲基苯基)亚甲基]-庚醛(Acalea)、异戊氧基乙酸烯丙酯(烯丙基戊基甘醇)、(3,3-二甲基环己基)乙基乙基丙烷-1,3-二酸酯(Applelide)、(E/Z)-1-乙氧基-1-癸烯(Arctical)、2-乙基-4-(2,2,3-三甲基-3-环-戊烯-1-基)-2-丁烯-1-醇(Bacdanol)、2-甲基-3-[(1,7,7-三甲基双环[2.2.1]庚-2-基)氧基]外-1-丙醇(Bornafix),1,2,3,5,6,7-六氢-1,1,2,3,3-五甲基-4H-茚-4-酮(Cashmeran)、三甲基环戊烯基甲基氧杂二环辛烷(Cassiffix)、1,1-二甲氧基-3,7-二甲基-2,6-辛二烯(CitralDMA)、3,7-二甲基-6-辛烯-1-醇(Citronellol)、3A,4,5,6,7,7A-六氢-4,7-亚甲基-1H-茚-5-/-6-基乙酸酯(Cyclacet)、3A,4,5,6,7,7A-六氢-4,7-亚甲基-1H-茚-5/-6-基丙酸酯(Cyclaprop)、3A,4,5,6,7,7A-六氢-4,7-亚甲基-1G-茚-5-/-6-基丁酸酯(Cyclobutanate)、1-(2,6,6-三甲基-3-环己烯-1-基)-2-丁烯-1-酮(DeltaDamascone)、3-(4-乙基苯基)-2,2-二甲基丙腈(Fleuranil)、3-(O/P-乙基苯基)-2,2-二甲基丙醛(Floralozone)、四氢-4-甲基-2-(2-甲基丙基)-2H-吡喃-4-醇(Floriffol)、1,3,4,6,7,8-六氢-4,6,6,7,8,8-六甲基环戊烯-γ-2-苯并吡喃(Galaxolide)、1-(5,5-二甲基-1-环己烯-1-基)戊-4-烯-1-酮(Galbascone)、E/Z-3,7-二甲基-2,6-辛二烯-1-基乙酸酯(GeranylAcetate)、α-甲基-1,3-苯并二氧杂环戊烯-5-丙醛(Helional)、1-(2,6,6-三甲基-2-环己烯-1-基)-1,6-庚二烯-3-酮(Hexalon)、(Z)-3-己烯基-2-羟基苯甲酸甲酯(HexenylSalicylate,CIS-3)、4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮(Iononeα)、1-(1,2,3,4,5,6,7,8-八氢-2,3,8,8-四甲基-2-萘基)-乙烷-1-酮(IsoESuper)、甲基-3-氧代-2-戊基环戊烷乙酸酯(Kharismal)、2,2,4-三甲基-4-苯基-丁腈(Khusinil)、3,4,5,6,6-五甲基庚-3-烯-2-酮(Koavone)、3/4-(4-羟基-4-甲基-戊基)环己烯-1-甲醛(Lyral)、3-甲基-4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮(MethylIononeγ),1-(2,6,6-三甲基-2-环己烯-1-基)戊-1-烯-3-酮(MethylIononeαExtra,MethylIononeN)、3-甲基-4-苯基丁-2-醇(Muguesia)、环戊烯并癸烷-4-烯-1-酮(MuskZ4)、3,3,4,5,5-五甲基-11,13-二氧杂三环[7.4.0.0<2,6>]十三碳醛-2(6)-烯(Nebulone)、3,7-二甲基-2,6-辛二烯-1-基乙酸酯(NerylAcetate)、3,7-二甲基-1,3,6-辛三烯(Ocimene)、邻-甲苯基乙醇(Peomosa)、3-甲基-5-苯基戊醇(Phenoxanol)、1-甲基-4-(4-甲基-3-戊烯基)环己-3-烯-1-甲醛(PrecyclemoneB)、4-甲基-8-亚甲基-2-金刚烷醇(Prismantol)、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(Sanjinol)、2-甲基-4-(2,2,3-三甲基-3--环戊烯-1-基)-2-丁烯-1-醇(Santaliff)、松油醇、2,4-二甲基-3-环己烯-1-甲醛(Triplal)、十氢-2,6,6,7,8,8-六甲基-2H-茚并[4,5-B]呋喃(Trisamber)、2-叔丁基环己基乙酸酯(Verdox)、4-叔丁基环己基乙酸酯(Vertenex)、乙酰基柏木烯(Vertofix)、3,6/4,6-二甲基环己-3-烯-1-甲醛(Vertoliff)和(3Z)-1-[(2-甲基-2-丙烯基)氧基]-3-己烯(Vivaldie)。
如本文所用,术语“食品”包括用于人或动物的固体和液体的可摄取材料,其中该材料通常具有但不必须具有营养价值。因此,所述食品包括肉类、肉汁、汤、方便食品、麦芽、酒精和其它饮料、牛奶和奶制品、海产品(包括鱼类、甲壳类和软体动物等)、糖果、蔬菜、谷类、软饮料、小吃、狗粮和猫粮以及其它兽用产品等。
术语“风味组合物”和“风味制剂”理解为具有相同的含义,并且是指产生令人愉悦的或期望的风味的消费性组合物(consumercomposition)。风味组合物含有化合物或化合物的混合物。本发明的风味组合物是包含2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛的消费性组合物。
术语“香味组合物(fragrancecomposition)”、“香味制剂(fragranceformulation)”和“加香组合物(perfumecomposition)”理解为具有相同的含义,并且指为化合物混合物的消费性组合物,该化合物包括例如醇、醛、酮、酯、醚、内酯、腈、天然油、合成油和硫醇,其被混合使得各个组分的合并气味产生令人愉悦的或期望的香味。本发明的香味组合物是包含2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛的消费性组合物。本发明的香味组合物包含2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛以及还包含如上所定义的补充香味化合物。
术语“香味产品”是指含有加香或掩盖恶臭的香味成分的消费性产品。香味产品可以包括例如香精;古龙水;香皂;液体香皂;沐浴露;泡泡浴;化妆品;护肤品(如面霜、乳液和剃须产品);护发产品(如洗发剂、清洗剂、调理剂、漂白剂、着色剂、染色剂、定型剂);除臭剂和止汗剂;女性护理产品,如卫生棉条和妇女卫生巾;婴儿护理产品,如尿布、围兜和湿巾;家庭护理产品,如浴室纸(bathtissues)、面巾纸、手帕纸或擦手纸;织物产品如织物柔软剂和清新剂;空气护理产品如空气清新剂和香味递送体系;化妆品制剂;清洁剂和消毒剂如洗涤剂、洗碗剂、去污组合物;玻璃和金属清洁剂,如窗户清洁剂;台面清洁剂;地板和地毯清洁剂;洁厕剂和漂白添加剂;洗涤剂如多用途洗涤剂、重型洗涤剂、和手洗或精细织物洗涤剂,包括衣物洗涤剂和漂洗添加剂;牙科和口腔卫生用品,如牙膏、牙胶、牙线、假牙清洁剂、义齿粘合剂、牙粉、牙齿美白和漱口水;医疗保健和营养产品以及食品,如小吃和饮料产品。本发明的香味组合物是含有2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛的消费性产品。本发明的香味产品含有2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛且还含有如上所定义的补充香味化合物。
术语“改善”理解为将风味或香味组合物提升至更合意的特征(character)。术语“增强”理解为使风味或香味组合物的效力提升或为所述风味或香味组合物提供改善的特征。术语“改性”理解为赋予风味或香味组合物特征上的变化。
术语“嗅觉可接受的量”理解为风味或香味制剂中化合物的量,其中该化合物将贡献其独特的嗅觉特性。但是,风味或香味制剂的嗅觉效果将是风味或香味成分各自的效果的总和。因此,可以使用2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛以改善或增强风味或香味制剂的香气特性,或通过改性制剂中其它成分所贡献的嗅觉反应来改善或增强风味或香味制剂的香气特性。该嗅觉可接受的量将随着许多因素,包括其它成分、其相对量和所期望的嗅觉效果而改变。
通常,风味组合物中所采用的2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛的嗅觉可接受的量以重量计为大于每十亿份约0.1份、优选每十亿份约1份至每百万份约1000份、更优选每十亿份约10份至每百万份约100份、甚至更优选每十亿份约100份至每百万份约10份。香味组合物中所采用的2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛的嗅觉可接受的量从约0.005至约70wt%变化,优选0.05至约50wt%、更优选约0.5至约25wt%,并且甚至更优选约1至约10wt%。本领域技术人员将能够采用期望的量以提供期望的风味或香味效果和强度。除了本发明的化合物之外,也可以使其它材料与该风味或香味组合物结合使用于包封(encapsulate)和/或递送风味或香味。一些公知的材料是例如但不限于聚合物;低聚物;其它非聚合物,如表面活性剂、乳化剂;脂质包括脂肪、蜡和磷脂;有机油;矿物油;石蜡(petrolatum);天然油;香水固定剂;纤维;淀粉;糖和固体表面材料,例如沸石和二氧化硅。
当在香味制剂中使用时,这些成分提供额外的香调使得香味制剂更合意和引人注目,并增加感知值。这些材料中发现的气味品质有助于美化和增强成品的一致性以及改善香味制剂中其它材料的性能。
另外,还令人惊讶地发现本发明的化合物提供优良的成分性能并在恶臭冲消应用如对身体汗液,环境气味如霉菌味和霉味,以及浴室等方面具有出乎意料的优点。本发明的化合物基本上消除了恶臭的感知和/或防止这样的恶臭形成,因此其可以用于众多的功能性产品中。
在此提供功能性产品的实例以说明本发明的各个方面。然而,其不意欲限制本发明的范围。功能性产品可以包括例如常规的房间清新剂(或除臭剂)组合物,如房间清新剂喷雾剂、气雾剂或其它喷雾剂;香味扩散剂;芯或其它液体系统,或固体,例如如香盒或塑料中的蜡烛或蜡碱;香袋或干喷雾剂中的粉末或如在固体凝胶棒中的凝胶;如洗衣机应用中使用的衣物除臭剂,如洗涤剂、粉末、液体、增白剂或织物柔软剂、织物清新剂、亚麻喷雾剂;应用在壁橱(closetblocks)、壁橱气溶胶喷雾剂(closetaerosolsprays)、或衣服存储区域中或应用在干洗中以克服衣服上残留的溶剂香调;浴室配件如纸巾(papertowels)、浴室纸、卫生巾、湿巾、一次性洗布、一次性尿布和尿布桶除臭剂;清洁剂如消毒剂和抽水马桶清洁剂;化妆品如止汗剂和除臭剂;粉剂、气雾剂、液体或固体形式的一般身体除臭剂;或头发护理产品如发胶、调理剂、冲洗剂、头发着色剂和染色剂、烫发剂、脱毛剂、直发剂;爽发膏应用如润发油、霜剂和乳液;含有如二硫化硒、煤焦油或水杨酸盐等成分的含药护发产品或洗发剂;或足部护理产品如爽足粉、液体或古龙水;须后水和身体乳液;或皂和合成洗涤剂如皂条、液体、泡沫或粉末;气味控制如制造过程中,例如纺织整理业和印刷业(油墨和纸)中的气味控制;流出物控制如涉及制浆、畜牧场和肉类处理工艺中的流出物控制;污水处理;垃圾袋或垃圾处置;或者产品的气味控制,如纺织制成品、橡胶制成品或汽车空气清新剂;农业和宠物护理产品,如狗和鸡舍的废水以及家畜和宠物护理产品,如除臭剂,洗发剂或清洁剂;或动物用厕所材料和在大规模封闭式系统,如礼堂、地铁和运输系统中的气味控制。
因此,可以看出,本发明的组合物通常是其中恶臭冲消剂与载体一起存在的组合物,利用该载体或通过该载体所述恶臭冲消剂可以被引入到其中存在恶臭的空气空间内,或引入到其上沉积有恶臭的基底。例如,载体可以是气溶胶推进剂如氯氟甲烷,或固体如蜡、塑料材料、橡胶、惰性粉末或凝胶。在芯型空气清新剂中,载体是低挥发性的基本上无味的液体。在一些应用中,本发明的组合物含有表面活性剂或消毒剂,而在其它应用中,恶臭冲消剂存在于纤维基底上。在本发明的许多组合物中也存在香味组分,其赋予组合物香味。可以采用所有的上述香料。
恶臭冲消的有效量应理解为功能性产品中采用的本发明的恶臭冲消剂在感官有效地消减给定的恶臭同时感官有效地降低气味水平的组合强度方面的量,其中给定的恶臭是存在于空气空间中或已沉积于基底上。所采用的恶臭冲消剂的确切量可以随着恶臭冲消剂的类型、所采用的载体类型和所期望的恶臭冲消剂的水平而变化。在一般情况下,存在的恶臭冲消剂的量是获得希望结果所需要的普通剂量。这种剂量是本领域技术人员所熟知的。在一个优选的实施方式中,当与恶臭固体或液体功能性产品如皂和洗涤剂结合使用时,本发明的化合物可以以约0.005至约50wt%、优选约0.01至约20wt%和更优选约0.05至约5wt%的量存在,并且当与恶臭的气体的功能性产品结合使用时,本发明的化合物可以以每立方米空气约0.1至10毫克的量存在。
下面将提供本发明的具体实施方式。本发明的其它修改对本领域技术人员将是显而易见的。此类修改理解为在本发明的范围内。除非另行说明,本文中所用的所有百分比是重量百分比,ppm理解为代表每百万份的份数,mL理解为毫升,g理解为克,mol理解为摩尔且mmol理解为毫摩尔。实施例中使用的IFF理解为是指InternationalFlavors&FragrancesInc.,NewYork,NY,USA
实施例I
制备2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛(式I):将甲醇钠(CH3ONa)(16.2g,0.3mol)溶解于甲醇(MeOH)(100mL)中。逐滴加入3-(乙酰硫基)-己醛(25g,0.1mol)。滴加完成后,将反应混合物在室温下再搅拌2小时。然后添加冰水(200mL),用氯化氢(HCl)(10%)使反应混合物酸化至pH为2。将所得混合物用乙酸乙酯(EtOAc)(200mL)萃取。将有机层依次用盐水、碳酸氢钠溶液(NaHCO3)(10%)和盐水洗涤,干燥并浓缩以提供粗产物。将粗产物蒸馏,用硅胶柱(乙酸乙酯/己烷)进一步纯化,得到2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛(12g)。
1HNMR(CDCl3,400MHz):9.32(s,1H),6.79(dd,1H,J=5.3,2.8Hz),3.51(m,1H),2.92-3.05(m,1H),2.61-2.75(m,1H),2.22-2.38(m,1H),1.35-1.76(m,8H),0.95(t,3H,J=7.1Hz),0.93(t,3H,J=6.9Hz)。
2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛(在水中,1%)描述为具有水果、绿叶、黑醋栗(cassis)、香薄荷(savory)和辛辣的特性。
实施例II
制备2,6-二甲基-5,6-二氢-2H-噻喃-3-甲醛(式Ⅱ):使用S-(4-氧代丁-2-基)-乙烷硫酯(100g,0.684mol)类似地制备2,6-二甲基-5,6-二氢-2H-噻喃-3-甲醛(4.8g)。
1HNMR(CDCl3,500MHz):9.33(s,1H),6.80(dd,J=5.4,2.5Hz,1H),3.70(q,J=6.9Hz,1H),3.10-3.18(m,1H),2.67-2.74(m,1H),2.24-2.40(m,1H),1.47(d,J=6.9Hz,3H),1.34(d,J=6.6Hz,3H)
实施例III
制备5,6-二氢-2H-噻喃-3-甲醛(式III):混合双(3,3-二乙氧基丙基)硫烷(50g,0.17mol)、水(69.4mL,3.855mol)、对甲苯磺酰氯(1.619g,8.49mmol)和1,4-二噁烷(100mL,1.174mol),并在80℃下搅拌约2小时。将反应物冷却至室温。添加水,将反应混合物用乙醚((C2H5)2O)萃取。将有机层依次用饱和碳酸氢钠溶液、水和盐水洗涤,然后干燥并浓缩以提供粗产物。粗产物用硅胶柱(乙酸乙酯/己烷,1:20)进一步纯化,得到5,6-二氢-2H-噻喃-3-甲醛(3.2g)。
1HNMR(CDCl3,400MHz):9.37(s,1H),6.86-6.96(m,1H),3.29-3.36(m,2H),2.79(t,J-5.6Hz,2H),2.63-2.72(m,2H)
实施例IV
制备上述化合物(即式I至III)每一个在水中一系列浓度的溶液。以下评价和报告了每个化合物在每个浓度下的感官性质:
在所有的测试浓度中,式I化合物表现出高度期望的水果味和热带气息香调,而式II和式III的化合物表现出令人排斥的异味(off-notes)。
Claims (14)
1.一种风味组合物,其包含嗅觉可接受的量的2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛。
2.如权利要求1所述的风味组合物,其还包含选自食品、口香糖、牙科产品、口腔卫生产品和医药产品的材料。
3.如权利要求1所述的风味组合物,其中所述嗅觉可接受的量为所述风味组合物重量的每十亿份约1份至每百万份约1000份。
4.如权利要求1所述的风味组合物,其中所述嗅觉可接受的量为所述风味组合物重量的每十亿份约10份至每百万份约100份。
5.如权利要求1所述的风味组合物,其中所述嗅觉可接受的量为所述风味组合物重量的每十亿份约100份至每百万份约10份。
6.一种通过添加嗅觉可接受的量的2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛来改善、增强或改性风味组合物的方法。
7.如权利要求6所述的方法,其中所述风味组合物还包含选自食品、口香糖、牙科产品、口腔卫生产品和医药产品的材料。
8.如权利要求6所述的方法,其中所述嗅觉可接受的量为所述风味组合物重量的每十亿份约1份至每百万份约1000份。
9.如权利要求6所述的方法,其中所述嗅觉可接受的量为所述风味组合物重量的每十亿份约10份至每百万份约100份。
10.如权利要求6所述的方法,其中所述嗅觉可接受的量为所述风味组合物重量的每十亿份约100份至每百万份约10份。
11.一种香味组合物,其包含嗅觉可接受的量的2,6-二丙基-5,6-二氢-2H-噻喃-3-甲醛。
12.如权利要求11所述的香味组合物,其中所述嗅觉可接受的量为所述香味组合物重量的每十亿份约1份至每百万份约1000份。
13.如权利要求11所述的香味组合物,其中所述嗅觉可接受的量为所述香味组合物重量的每十亿份约10份至每百万份约100份。
14.如权利要求11所述的香味组合物,其中所述嗅觉可接受的量为所述香味组合物重量的每十亿份约100份至每百万份约10份。
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US3733336A (en) * | 1969-04-17 | 1973-05-15 | Degussa | Process for the production of 5,6-dihydro-2h-thiopyran-3-carboxaldehyde |
JPS6137779A (ja) * | 1984-07-25 | 1986-02-22 | バスフ アクチェン ゲゼルシャフト | 5,6‐ジヒドロ‐2h‐チオピラン‐3‐カルボキシアルデヒドの製法 |
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US4534891A (en) | 1982-11-12 | 1985-08-13 | International Flavors & Fragrances Inc. | Branched C13 -alk-1-en-5-ones and use thereof in perfumery |
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US3733336A (en) * | 1969-04-17 | 1973-05-15 | Degussa | Process for the production of 5,6-dihydro-2h-thiopyran-3-carboxaldehyde |
JPS6137779A (ja) * | 1984-07-25 | 1986-02-22 | バスフ アクチェン ゲゼルシャフト | 5,6‐ジヒドロ‐2h‐チオピラン‐3‐カルボキシアルデヒドの製法 |
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