CN115418269A - 包含新戊二醇二乙酸酯的芳香和香料组合物 - Google Patents
包含新戊二醇二乙酸酯的芳香和香料组合物 Download PDFInfo
- Publication number
- CN115418269A CN115418269A CN202210930929.9A CN202210930929A CN115418269A CN 115418269 A CN115418269 A CN 115418269A CN 202210930929 A CN202210930929 A CN 202210930929A CN 115418269 A CN115418269 A CN 115418269A
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- CN
- China
- Prior art keywords
- fragrance
- composition
- perfume
- neopentyl glycol
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003205 fragrance Substances 0.000 title claims abstract description 191
- ZFFGZCTVZNNVLP-UHFFFAOYSA-N (3-acetyloxy-2,2-dimethylpropyl) acetate Chemical compound CC(=O)OCC(C)(C)COC(C)=O ZFFGZCTVZNNVLP-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 title claims description 150
- 239000002304 perfume Substances 0.000 title claims description 78
- 239000004615 ingredient Substances 0.000 claims abstract description 60
- -1 conditioner Substances 0.000 claims description 57
- 239000000654 additive Substances 0.000 claims description 38
- 239000000796 flavoring agent Substances 0.000 claims description 20
- 235000019634 flavors Nutrition 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 230000000996 additive effect Effects 0.000 claims description 12
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical group CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 9
- 239000001069 triethyl citrate Substances 0.000 claims description 9
- 235000013769 triethyl citrate Nutrition 0.000 claims description 9
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002537 cosmetic Substances 0.000 claims description 7
- 235000013305 food Nutrition 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
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- 239000012895 dilution Substances 0.000 claims description 5
- 238000010790 dilution Methods 0.000 claims description 5
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- 239000000047 product Substances 0.000 description 51
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
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- 239000000463 material Substances 0.000 description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 12
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- 238000000034 method Methods 0.000 description 10
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- 239000003814 drug Substances 0.000 description 9
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
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- 239000000872 buffer Substances 0.000 description 6
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 6
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 6
- UNYNVICDCJHOPO-UHFFFAOYSA-N sotolone Chemical compound CC1OC(=O)C(O)=C1C UNYNVICDCJHOPO-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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- 241000402754 Erythranthe moschata Species 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 5
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 5
- 235000009508 confectionery Nutrition 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 5
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 4
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 4
- WRYLYDPHFGVWKC-UHFFFAOYSA-N 4-terpineol Chemical compound CC(C)C1(O)CCC(C)=CC1 WRYLYDPHFGVWKC-UHFFFAOYSA-N 0.000 description 4
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- 238000004458 analytical method Methods 0.000 description 4
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Abstract
本申请涉及新戊二醇二乙酸酯(CAS 13431‑57‑7)作为香料和芳香成分的用途。
Description
本申请是申请号为201680017567.7、申请日为2016年1月22日、发明名称为“包含新戊二醇二乙酸酯的芳香和香料组合物”的专利申请的分案申请。
相关申请的交叉引用
本申请要求2015年1月23日提交的美国临时申请No.62/107,219和2015年6月18日提交的美国临时申请No.62/181,480的优先权和权益,通过引用将二者的内容全部结合到本文中。
申请领域
本申请涉及新戊二醇二乙酸酯(CAS No.13431-57-7)在香料和芳香组合物中的用途。
背景
对许多消费品而言,气味是用于产生预期感觉、质量、美味和安全性的重要因素。确定有效的芳香和香味赋予产品是贡献于产品成功,并且在产品市场、消费者满意度和消费者保持力中有用的一个元素。香甜的树脂气味是特别理想的香味,并且通常用于盥洗用品、化妆品、家用清洁剂、房间用喷雾、洗衣和精细香味应用,例如香料和花露水中。类似的香味在许多牙齿用卫生产品、口服药物和食品中也是理想的。
新戊二醇二乙酸酯描述于文献中并且表征为用于工业和加工用途的环境优选的流体(US 6818049 B1、WO 200206487 A1、WO 9957217 A1)、用于油漆的酯组合物(WO9832728 A1)、多晶硅组合物(HU 62623 A2,J.Coatings Tech.(1988),60(759),53-6)中,以及作为挥发性化合物用于来自Glassline packages的可固化涂料(J.Food Sci.(1989),54(3),770-3)中。
然而,新戊二醇二乙酸酯没有被描述和表征为用于香料和芳香应用的化合物。本申请描述新戊二醇二乙酸酯惊讶和出乎意料的嗅觉质量及其作为容易得到且划算的芳香和香料成分的用途及其潜在应用。本申请进一步描述新戊二醇二乙酸酯作为溶剂的用途及其潜在应用。
概述
在一个方面中,本申请涉及包含新戊二醇二乙酸酯的芳香组合物:
在另一方面中,本申请涉及芳香组合物,其包含新戊二醇二乙酸酯和一种或多种添加剂、其它芳香成分,或者添加剂和芳香成分的组合。
在另一方面中,本申请涉及包含新戊二醇二乙酸酯的香料组合物:
在另一方面中,本申请涉及香料组合物,其包含新戊二醇二乙酸酯和一种或多种添加剂、其它香料成分,或者添加剂和香料成分的组合。
在另一方面中,本申请涉及包含含有新戊二醇二乙酸酯的溶剂的各种组合物。
本申请的一个或多个实施方案的细节描述于下面所附描述中。除非另外定义,本文所用所有技术和科学术语具有与本申请属于的领域中的技术人员通常理解的相同含义。在矛盾的情况下,对照本说明书。
本申请的其它特征和优点从以下详细描述、实施例和权利要求书中获悉。
附图简述
图1为通过GC-FID对新戊二醇二乙酸酯的纯度的分析。
图2为新戊二醇二乙酸酯的13C NMR谱。
详述
新戊二醇二乙酸酯具有独特的芳香和香味。因此确定它在对它加入其中的产品赋予和提供理想的芳香和/或香味中是有用的。例如,新戊二醇二乙酸酯可用于想要包括愉悦芳香和香味的任何产品中,包括但不限于香料、家用产品、洗衣产品、个人护理产品、化妆品、牙齿用卫生产品、口服药物和食品。取决于具体芳香或香料产品应用、存在的其它带有气味的成分的性质和量以及产品的所需芳香和/或香味,新戊二醇二乙酸酯可以以变化量使用。
新戊二醇二乙酸酯可通过例如用乙酸酐或冰乙酸将新戊二醇乙酰化而制备。示例的制备显示于下文中:
新戊二醇二乙酸酯也可通过新戊二醇与乙酸缩合,通过用乙酰氯将新戊二醇乙酰化或者通过任何其它乙酰化方法制备。
新戊二醇二乙酸酯的芳香可通过在芳香吸纸上测试化合物而评估,所述芳香吸纸为用于将含水形式的化合物取样的小纸条。不是直接由包含芳香成分的小瓶中闻它,芳香吸纸用于提供给定芳香成分的气味的更准确代表。包含芳香成分的小瓶的表面上的芳香主要包含芳香的顶香,其为强的,但快速蒸发。因此,芳香吸纸的使用提供新戊二醇二乙酸酯总体气味的更好表示,包括其中香和底香,这构成当它被赋予产品中时,由成分经历的主要气味。
当新戊二醇二乙酸酯在不存在其它芳香成分下(纯净的)存在于芳香吸纸上时,它具有初始芳香,其可描述为清新、甜、果味、树脂和没药状的,具有脂肪香。
此外,新戊二醇二乙酸酯以在柠檬酸三乙酯中的10%稀释物,具有愉悦的芳香效应。吸纸上的香气持久力,经给定时间检测的芳香能力,为约5-10小时。纯净或为溶液的新戊二醇二乙酸酯因此可用于芳香和香料组合物中以赋予甜、清新、愉悦的芳香和/或香味。
如本文所用,术语“芳香组合物”意指用于提供给产品所需气味的溶于合适溶剂中或者与粉状基质混合的芳香成分的混合物,如果需要的话包括辅助物质。具有芳香组合物的产品的实例包括但不限于香料、皂、昆虫驱避剂和杀虫剂、洗涤剂、家用清洁剂、空气清新剂、房间用喷雾、香丸、蜡烛、化妆品、花露水、须前和须后水、滑石粉、护发产品、身体用除臭剂、止汗药和宠物垫材。
如本文所用,术语“香料组合物”意指用于提供给产物所需香味的溶于合适溶剂中或者与粉状基质混合的香料成分的混合物,如果需要的话包括辅助物质。具有香料组合物的产品的实例包括但不限于牙齿用卫生产品,例如漱口水、牙膏、牙线和口气清新剂,口服药物,包括液体、片剂或胶囊,和食品。
可与用于生产芳香和香料组合物的所述化合物组合使用的芳香和香料成分以及芳香和香料成分的混合物包括但不限于天然产品,包括提取物、动物产品和精油、净油、类树脂、树脂和混凝土,和合成芳香材料,包括但不限于醇、醛、酮、醚、酸、酯、乙缩醛、苯酚、醚、内酯、呋喃酮缩醇、腈、酸,和烃,包括饱和和不饱和化合物,以及脂族碳环和杂环化合物,和动物产品。如本文所用,术语“芳香成分”和“香料成分”指不同于新戊二醇二乙酸酯的成分。本申请涉及新戊二醇二乙酸酯,在本文中也称为本申请“化合物”,作为具有理想芳香和香味性能的化合物,使得它可被考虑用作新型香料和芳香成分。为了清晰,新戊二醇由该名称或者由本申请“化合物”指代以将它与用于香料和芳香组合物中的已知芳香和香料成分区分。
可用于本申请的芳香和香料组合物中的酯的实例包括但不限于丙烯酸酯(甲基、乙基等),乙酰乙酸酯(甲基、乙基等),茴香酸酯(甲基、乙基等),苯甲酸酯(烯丙基、异戊基、乙基、香叶基、里哪基、苯基乙基、己基、顺-3-己烯基、苄基、甲基等),邻氨基苯甲酸酯(肉桂基、顺-3-己烯基、甲基、乙基、里哪基、异丁基等),N-甲基邻氨基苯甲酸酯(甲基、乙基等),异戊酸酯(戊基、烯丙基、异戊基、异丁基、异丙基、乙基、辛基、香叶基、环己基、香茅基、萜烯基、里哪基、肉桂基、苯基乙基、丁基、丙基、己基、苄基、甲基、玫瑰基等),异丁酸酯(异戊基、香叶基、香茅基、萜烯基、肉桂基、辛基、nellyl、苯基乙基、苯基丙基、苯氧基乙基、丁基、丙基、异丙基、己基、苄基、甲基、乙基、里哪基、玫瑰基等),十一碳烯酸酯(烯丙基、异戊基、丁基、乙基、甲基等),辛酸酯(烯丙基、异戊基、乙基、辛基、己基、丁基、甲基、里哪基等),辛烯酸酯(甲基、乙基等),辛炔羧酸酯(甲基、乙基等),己酸酯(烯丙基、戊基、异戊基、甲基、乙基、异丁基、丙基、己基、顺-3-己烯基、反-2-己烯基、里哪基、香叶基、环己基等),己烯酸酯(甲基、乙基等),戊酸酯(戊基、异丙基、异丁基、乙基、顺-3-己烯基、反-2-己烯基、肉桂基、苯基乙基、甲基等),甲酸酯(茴香基、异戊基、异丙基、乙基、辛基、香叶基、香茅基、肉桂基、环己基、萜烯基、苯基乙基、丁基、丙基、己基、顺-3-己烯基、苄基、里哪基、玫瑰基等),巴豆酸酯(异丁基、乙基、环己基等),肉桂酸酯(烯丙基、乙基、甲基、异丙基、丙基、3-苯基丙基、苄基、环己基、甲基等),琥珀酸酯(单薄荷基、二乙基、二甲基等),乙酸酯(茴香基、戊基、α-戊基肉桂基、异戊基、异丁基、异丙基、异冰片基、异丁子香基、丁子香基、2-乙基丁基、乙基、3-辛基、对甲苯基、邻甲苯基、香叶基、α-或β-檀香基、环己基、环橙花基、二氢枯茗基、二甲基苄基甲基、肉桂基、苏合香基、癸基、十二烷基、萜烯基、愈创木基、橙花基、壬基、苯基乙基、苯基丙基、丁基、糠基、丙基、己基、顺-3-己烯基、反-2-己烯基、顺-3-壬烯基、顺-6-壬烯基、顺-3-顺-6-壬二烯基、3-甲基-2-丁烯基、庚基、苄基、冰片基、月桂烯基、二氢月桂烯基、桃金娘烯基、甲基、2-甲基丁基、薄荷基、里哪基、玫瑰基等),水杨酸酯(烯丙基、异戊基、苯基、苯基乙基、苄基、乙基、甲基等),环己基链烷酸酯(环己基乙酸乙酯、环己基丙酸烯丙基酯、环己基丁酸烯丙基酯、环己基己酸烯丙基酯、环己基癸酸烯丙基酯、环己基戊酸烯丙基酯等),硬脂酸酯(乙基、丙基、丁基等),癸二酸酯(二乙基、二甲基等),癸酸酯(异戊基、乙基、丁基、甲基等),十二烷酸酯(异戊基、乙基、丁基等),乳酸酯(异戊基、乙基、丁基等),壬酸酯(乙基、苯基乙基、甲基等),壬烯酸酯(烯丙基、乙基、甲基等),羟基己酸酯(乙基、甲基等),苯基乙酸酯(异戊基、异丁基、乙基、香叶基、香茅基、顺-3-己烯基、甲基等),苯氧基乙酸酯(烯丙基、乙基、甲基等),呋喃羧酸酯(呋喃羧酸乙酯、呋喃羧酸甲酯、呋喃羧酸己酯、呋喃新戊二醇二乙酸丙酸异丁基酯等),丙酸酯(茴香基、烯丙基、乙基、戊基、异戊基、丙基、丁基、异丁基、异丙基、苄基、香叶基、环己基、香茅基、肉桂基、四氢糠基、三环癸烯基、庚基、冰片基、甲基、薄荷基、里哪基、萜烯基、α-甲基丙酰基、β-甲基丙酰基等),庚酸酯(烯丙基、乙基、辛基、丙基、甲基等),庚炔羧酸酯(烯丙基、乙基、丙基、甲基等),肉豆蔻酸酯(异丙基、乙基、甲基等),苯基缩水甘油酸酯(苯基缩水甘油酸乙酯、3-甲基苯基缩水甘油酸乙酯、对甲基-β-苯基缩水甘油酸乙酯等),2-甲基丁酸酯(甲基、乙基、辛基、苯基乙基、丁基、己基、苄基等),3-甲基丁酸酯(甲基、乙基等),丁酸酯(茴香基、戊基、烯丙基、异戊基、甲基、乙基、丙基、辛基、愈创木基、里哪基、香叶基、环己基、香茅基、肉桂基、nellyl、萜烯基、苯基丙基、β-苯基乙基、丁基、己基、顺-3-己烯基、反-2-己烯基、苄基、玫瑰基等),和羟基丁酸酯(3-羟基丁酸酯的甲基、乙基、薄荷基等)。
可用于本申请的芳香和香料组合物中的醇的实例包括但不限于脂族醇(异戊醇、2-乙基己醇、1-辛醇、3-辛醇、1-辛烯-3-醇、1-癸醇、1-十二醇、2,6-壬二烯醇、壬醇、2-壬醇、顺-6-壬烯醇、反-2、顺-6-壬二烯醇、顺-3、顺-6-壬二烯醇、丁醇、己醇、顺-3-己烯醇、反-2-己烯醇、1-十一醇、庚醇、2-庚醇、3-甲基-1-戊醇等);萜烯醇(冰片、异冰片、香芹醇、香叶醇、α-或β-白檀油烯醇、香茅醇、4-侧柏醇、萜品醇、4-萜品醇、橙花醇、月桂烯醇、桃金娘烯醇、二氢月桂烯醇、四氢月桂烯醇、橙花叔醇、羟基香茅醇、法呢醇、紫苏醇、玫红醇、里哪醇等);和芳族醇(茴香醇、α-戊基肉桂醇、异丙基苄基甲醇、香芹酚、枯茗醇、二甲基苄基甲醇、肉桂醇、苯基烯丙醇、苯乙基甲醇、β-苯基乙醇、3-苯基丙醇、苄醇等)。
可用于本申请的芳香和香料组合物中的醛的实例包括但不限于脂族醛(乙醛、辛醛、壬醛、癸醛、十一醛、2,6-二甲基-5-庚醛、3,5,5-三甲基己醛、顺-3、顺-6-壬二烯醛、反-2、顺-6-壬二烯醛、戊醛、丙醛、异丙醛、己醛、反-2-己醛、顺-3-己醛、2-庚醛、十二醛、十四醛、反-4-癸烯醛、反-2-十三烯醛、反-2-十二烯醛、反-2-十一烯醛、2,4-己二烯醛、顺-6-壬烯醛、反-2-壬烯醛、2-甲基丁醛等);芳族醛(茴香醛、α-戊基肉桂醛、α-甲基肉桂醛、兔耳草醛、p-异丙基苯基乙醛、乙基香草醛、枯茗醛、水杨醛、肉桂醛、邻-、间-或对-甲苯醛、香草醛、洋茉莉醛、苯基乙醛、胡椒醛、苯甲醛、4-甲基-2-苯基-2-庚醛、对-甲氧基肉桂醛、对-甲氧基苯甲醛等);和萜烯醛(香叶醛、柠檬醛、香茅醛、α-甜橙醛、β-甜橙醛、紫苏醛、羟基香茅醛、四氢柠檬醛、桃金娘烯醛、环柠檬醛、异环柠檬醛、香茅基氧基乙醛、橙花醛、α-亚甲基香茅醛、柑青醛、新铃兰醛、藏花醛等)。
可用于本申请的芳香和香料组合物中的酮的实例包括但不限于环酮(1-乙酰基-3,3-二甲基-1-环己烯、顺-茉莉酮、α-、β-或γ-鸢尾酮、乙基麦芽酚、甲基环戊烯醇酮、二氢诺卡酮、3,4-二甲基-1,2-环戊二酮、4,5-二甲基-3-羟基-2(5H)-呋喃酮(sotolon)、α-、β-、γ-或δ-大马酮、α-、β-或γ-大马酮、诺卡酮、2-仲丁基环己酮、麦芽酚、α-、β-或γ-紫罗酮、α-、β-或γ-甲基紫罗酮、α-、β-或γ-异甲基紫香酮、2,5-二甲基-4-羟基-3(2H)-呋喃酮(furaneol)、樟脑等);芳族酮(萘乙酮、苯乙酮、亚茴香基丙酮、覆盆子酮、对甲基苯乙酮、茴香基丙酮、对甲氧基苯乙酮等);链酮(二乙酰基、2-壬酮、二乙酰基、2-庚酮、2,3-庚二酮、2-戊酮、甲基戊基酮、甲基壬基酮、β-甲基萘酮、甲基庚酮、3-庚酮、4-庚酮、3-辛酮、2,3-己二酮、2-十一酮、二甲基辛烯酮、6-甲基-5-庚烯-2-酮等)。
可用于本申请的芳香和香料组合物中的乙缩醛的实例包括但不限于乙醛二乙基乙缩醛、乙醛二戊基乙缩醛、乙醛二己基乙缩醛、乙醛丙二醇乙缩醛、乙醛乙基顺-3-己烯基乙缩醛、苯甲醛甘油乙缩醛、苯甲醛丙二醇乙缩醛、柠檬醛二甲基乙缩醛、柠檬醛二乙基乙缩醛、柠檬醛丙二醇乙缩醛、柠檬醛乙二醇乙缩醛、苯基乙醛二甲基乙缩醛、香茅基甲基乙缩醛、乙醛苯基乙基丙基乙缩醛、己醛二甲基乙缩醛、己醛二己基乙缩醛、己醛丙二醇乙缩醛、反-2-己醛二乙基乙缩醛、反-2-己醛丙二醇乙缩醛、顺-3-己醛二乙基乙缩醛、庚醛二乙基乙缩醛、庚醛乙二醇乙缩醛、辛醛二甲基乙缩醛、壬醛二甲基乙缩醛、癸醛二甲基乙缩醛、癸醛二乙基乙缩醛、2-甲基十一醛二甲基乙缩醛、香茅醛二甲基乙缩醛、Ambersage(由Givaudan生产)、乙酰乙酸乙酯乙二醇乙缩醛和2-苯基丙醛二甲基乙缩醛。
可用于本申请的芳香和香料组合物中的苯酚的实例包括但不限于丁子香酚、异丁子香酚、2-甲氧基-4-乙烯基苯酚、麝香草酚、香芹酚、愈疮木酚和胡椒酚,和香草醛。
可用于本申请的香料和芳香组合物中的醚的实例包括但不限于茴香脑、1,4-桉树脑、二苄基醚、氧化里哪醇、氧化柠檬烯、橙花醚、玫瑰醚、甲基异丁子香酚、甲基胡椒酚、异戊基苯基***、β-萘基甲醚、苯基丙醚、对-甲苯基甲醚、香草基丁醚、α-萜烯甲醚、香茅基***、香叶基***、玫瑰呋喃、茶螺烷、癸基甲醚和甲基苯基甲醚。
可用于本申请的香料和芳香组合物中的内酯的实例包括但不限于γ-或δ-癸内酯、γ-庚内酯、γ-壬内酯、γ-或δ-己内酯、γ-或δ-辛内酯、γ-或δ-十一烷内酯、δ-十二烷内酯、δ-2-癸烯内酯、甲基内酯、5-羟基-8-十一碳烯酸δ-内酯、茉莉内酯、薄荷内酯、二氢香豆素、八氢香豆素和6-甲基香豆素。
可用于本申请的香料和芳香组合物中的呋喃的实例包括但不限于呋喃、2-甲基呋喃、3-甲基呋喃、2-乙基呋喃、2,5-二乙基四氢呋喃、3-羟基-2-甲基四氢呋喃、2-(甲氧基甲基)呋喃、2,3-二氢呋喃、糠醛、5-甲基糠醛、3-(2-呋喃基)-2-甲基-2-丙烯醛、5-(羟甲基)糠醛、2,5-二甲基-4-羟基-3(2H)-呋喃酮(furaneol)、4,5-二甲基-3-羟基-2(5H)-呋喃酮(sotolon)、2-乙基-4-羟基-5-甲基-3(2H)-呋喃酮(homofuraneol)、5-乙基-3-羟基-4-甲基-2(5H)-呋喃酮(homosotolon)、3-甲基-1,2-环戊二酮(cyclotene)、2(5H)-呋喃酮、4-甲基-2(5H)-呋喃酮、5-甲基-2(5H)-呋喃酮、2-甲基-3(2H)-呋喃酮、5-甲基-3(2H)-呋喃酮、2-乙酰基呋喃酮、2-乙酰基-5-甲基呋喃、糠醇、2-呋喃羧酸甲酯、2-呋喃羧酸乙酯和乙酸糠基酯。
可用于本申请的香料和芳香组合物中的烃的实例包括但不限于α-或β-红没药烯、β-石竹烯、对伞花烃、萜品烯、萜品油烯、杜松烯、柏木烯、长叶烯、法呢烯、柠檬油精、罗勒烯、月桂烯、α-或β-松萜、1,3,5-十一碳三烯和瓦伦烯。
可用于本申请的香料和芳香组合物中的酸的实例包括但不限于香叶酸、十二烷酸、肉豆蔻酸、硬脂酸、乳酸、苯基乙酸、丙酮酸、反-2-甲基-2-戊烯酸、2-甲基-顺-3-戊烯酸、2-甲基-4-戊烯酸和环己烷羧酸。
本申请的芳香和香料组合物可包含一种或多种天然提取物或油,包括但不限于茴芹、橙子、柠檬、酸橙、柑桔、橙叶、香柠檬、蜜蜂花、柚子、榄香、乳香、柠檬香草、橙花油、马郁兰、当归根、八角茴香、罗勒、月桂、菖蒲、甘菊、香菜、小豆蔻、桂皮、肉桂、胡椒、紫苏、柏木、牛至、西印度苦香树、姜、欧芹、松针、鼠尾草、牛膝草、茶树、芥菜、山葵、香紫苏、丁香、干邑(cognac)、胡荽、龙蒿、桉树、茴香、愈疮木、莳萝、白千层、土荆芥、甘椒、刺柏、胡芦巴、大蒜、月桂树、肉豆蔻、没药树、肉豆蔻、云杉、天竺葵、香茅、熏衣草、白鲑、玫瑰草、玫瑰、迷迭香、檀香、橡苔、柏木、香根草、沉香、bois de玫瑰、广藿香、劳丹脂、孜然芹、百里香、依兰、白桦、辣椒、旱芹、妥卢香脂、香猫、不雕花、安息香胶、茉莉、金合欢、晚香玉、木犀草、万寿菊、含羞草、红没药、鸢尾草、香草和欧亚甘草。这些天然提取物或油各自包含化合物的复杂混合物,其可包括上述那些化合物。其它芳香成分可由天然产物分离,例如香叶醇和香茅醛可由香茅油分离,柠檬醛可由柠檬草油分离,丁子香酚可由丁香油分离,且里哪醇可由红木油分离。芳香组合物中所用动物产物包括但不限于麝香、龙涎香、麝猫香和海狸香。本文所述天然成分也可合成地制备,并且可包括本文所述化合物,并作为芳香和/或香料成分用于本申请的芳香和香料组合物中。
用于香料、空气清新剂、衣物洗涤剂、宠物垫材、清洁产品、液体和条皂、洗发水和护发素、化妆品、除臭剂和个人卫生产品中的芳香成分的实例包括但不限于己基肉桂醛;戊基肉桂醛;水杨酸戊酯;水杨酸己酯;萜品醇;3,7-二甲基-顺-2,6-辛二烯-1-醇;2,6-二甲基-2-辛醇;2,6-二甲基-7-辛烯-2-醇;3,7-二甲基-3-辛醇;3,7-二甲基-反-2,6-辛二烯-1-醇;3,7-二甲基-6-辛烯-1-醇;3,7-二甲基-1-辛醇;2-甲基-3-(对-叔丁基苯基)-丙醛;4-(4-羟基-4-甲基戊基)-3-环己烯-1-甲醛;丙酸三环癸烯酯;乙酸三环癸烯酯;茴香醛;2-甲基-2-(对-异丙基苯基)-丙醛;3-甲基-3-苯基缩水甘油酸乙酯;4-(对-羟基苯基)-丁-2-酮;1-(2,6,6-三甲基-2-环己烯-1-基)-2-丁烯-1-酮;对-甲氧基苯乙酮;对-甲氧基-α-苯基丙烯;甲基-2-正己基-3-氧代-环戊烷羧酸酯;γ-十一内酯;香叶醇;乙酸香叶基酯;里哪醇;乙酸里哪基酯;四氢里哪醇;香茅醇;乙酸香茅基酯;二氢月桂烯醇;乙酸二氢月桂烯酯;四氢月桂烯醇;乙酸萜品酯;诺卜醇;乙酸诺卜酯;2-苯乙醇;乙酸2-苯基乙酯;苄醇;乙酸苄基酯;水杨酸苄基酯;苯甲酸苄基酯;乙酸苏合香酯;二甲基苄基甲醇;甲基苯基甲基乙酸三氯甲基苯基甲酯;乙酸异壬基酯;乙酸岩兰草酯;岩兰草醇;2-甲基-3-(对-叔丁基苯基)-丙醛;2-甲基-3-(对-异丙基苯基)-丙醛;3-(对-叔丁基苯基)-丙醛;4-(4-甲基-3-戊烯基)-3-环己烯醛;4-乙酰氧基-3-戊基四氢吡喃;二氢茉莉酮酸甲酯;2-正庚基环戊酮;3-甲基-2-戊基-环戊酮;正癸醛;正十二醛;9-癸烯醇-1;异丁酸苯氧基乙酯;苯基乙醛二甲基乙缩醛;苯基乙醛二乙基乙缩醛;香叶腈;香茅腈;柏木乙缩醛;3-异龙脑基环己醇;柏木基甲醚;异长叶烷酮;大茴香腈;茴香醛;胡椒醛;丁子香酚;香草醛;二苯醚;羟基香茅醛紫罗酮;甲基紫罗酮;异甲基紫罗酮;鸢尾酮;顺-3-己烯醇及其酯;茚满麝香芳香剂;萘满麝香芳香剂;异色满麝香芳香剂;大环酮;大环内酯麝香芳香剂;和巴西酸乙二醇酯。
给定产品芳香或香料组合物中的芳香和香料成分基于产品的意欲用途和产品的所需香味选择。例如,选择用于牙膏、漱口水和牙齿卫生产品中的香料成分以赋予“清新”,包括但不限于荷兰薄荷油、胡椒薄荷油、八角茴香油、柠檬油和薄荷醇。
香料组合物可用于掩蔽口服药物的不愉悦味道。例如,如果药物是咸味的,则可使用具有肉桂、悬钩子、橙子、枫木、奶油糖果或甘草(欧亚甘草)香味的香料组合物掩蔽该味道。如果药物是过甜的,则具有浆果、香草或***树胶香味的香料组合物可使药物更加美味。在苦味药物的情况下,可使用具有可可粉、巧克力-薄荷、野黑樱桃、胡桃、甘草(欧亚甘草)和圣草香味的香料组合物,而酸味药物可通过具有水果、柑橘或樱桃香味的香料组合物改进。这些香味可由本文所述天然或合成香料成分提供。
用于食品的香料组合物中的香料成分的实例包括但不限于葡糖基甜菊糖苷、异薄荷醇、硫代碳酸、cassyrane、1,5-辛二烯-3-醇、2-巯基庚-4-醇、4 3-(甲硫基)癸醛、(4Z,7Z)-十三碳-4,7-二烯醛、越南香菜油、Amacha叶提取物、谷氨酰-2-氨基丁酸、谷氨酰-2-氨基丁酸、谷氨酰-正缬氨酰-甘氨酸、0谷氨酰-正缬氨酸、N1-(2,3-二甲氧基苄基)-N2-(2-(吡啶-2-基)乙基)草酰胺、1-(2-羟基-4-甲基环己基)乙酮、墨西哥酸橙油、波斯酸橙油、6-甲氧基-2,6-二甲基庚醛、3,5-十一碳二烯-2-酮、2,5-十一碳二烯-1-醇、三乙基噻啶、4-甲基戊酸4-甲基戊基酯、(R)-N-(1-甲氧基-4-甲基戊烷-2-基)-3,4-二甲基苯甲酰胺、2N-乙酰基谷氨酸酯、1,3-丙二醇、四川胡椒提取物、Tasmannia党参提取物、Mentha长叶油、莽吉柿蒸馏物、3-(2-羟基苯基)丙酸乙酯、1-环丙烷甲基-4-甲氧基苯、硫代异丁酸异戊二烯基酯、硫代异戊酸异戊二烯基酯、马台树脂醇、甜菊苷、1-(2,4-二羟基苯基)-3-(3-羟基-4-甲氧基苯基)丙-1-酮、5-甲酰氧基癸酸乙酯、3-[3-(2-异丙基-5-甲基-环己基)脲基]丁酸乙酯、2-异丙基-4-甲基-3-噻唑啉、2,6,10-三甲基-9-十一烯醛、5-巯基-5-甲基-3-己酮、野柠檬油、teviol糖苷提取物、甜菊、甜菊糖A 60%、rubescenamine、4-氨基-5-(3-(异丙基氨基)-2,2-二甲基-3-氧代丙氧基)-2-甲基喹啉-3-羧酸、3-甲基-5-(2,2,3-三甲基环戊-3-烯-1-基)戊-4-烯-2-醇、(1-甲基-2-(1,2,2-三甲基二环[3.1.0]己-3-基甲基)环丙基)甲醇、erospicata油和卷曲薄荷油。参见L.J.Marnett等人,GRAS Flavoring Substances 26,Food Technology,44-45(2013)。
在一个方面中,提供包含新戊二醇二乙酸酯的芳香组合物。在一些实施方案中,芳香组合物可进一步包含一种或多种添加剂、一种或多种芳香成分,或者其组合。
根据实施方案,提供包含芳香组合物的产品,其中芳香组合物包含新戊二醇二乙酸酯。在一些实施方案中,该产品可包含其它物质,包括但不限于赋形剂或缓冲剂。
在另一方面中,提供包含新戊二醇二乙酸酯的香料组合物。在一些实施方案中,香料组合物可进一步包含一种或多种添加剂、一种或多种香料成分,或者其组合。
根据实施方案,提供包含香料组合物的产品,其中香料组合物包含新戊二醇二乙酸酯。在一些实施方案中,该产品可包含其它物质,包括但不限于赋形剂或缓冲剂。
根据实施方案,新戊二醇二乙酸酯可用作溶剂。愉悦的嗅觉性能、低挥发性和优异的溶解性使得新戊二醇二乙酸酯对用作想要愉悦气味的产品中的溶剂而言是理想的。例如,新戊二醇二乙酸酯可单独或者与其它溶剂材料组合用作溶剂以提供例如清洁组合物,包括清洁喷雾和工业清洁剂、空气清新剂、脱脂组合物、洗涤剂组合物、油漆组合物、涂料组合物和可获益于含有新戊二醇二乙酸酯的溶剂的其它产品的溶剂。可用于新戊二醇二乙酸酯溶剂体系中的其它溶剂材料可包括水溶性有机溶剂或油溶性有机溶剂。优选的溶剂包括但不限于柠檬酸三乙酯、醋精、甘油、乙醇、水、甘油三酯、液体蜡、丙二醇衍生物和乙二醇衍生物。
芳香或香料组合物中给定芳香或香料成分的量不能分类描述,因为它取决于加香或加味的产品类型、产品的意欲用途和产物的所需香味和/或味道而变化。芳香或香料组合物中芳香或香料成分的量通常为芳香组合物的约1%至约99质量%。当成分的量太小时,不能得到足够强度的香味或气味。另外,当成分的量太大时,可能需要将成分稳定的大量试剂,这在产品使用或消耗时又可能通过抑制挥发或者香味或芳香分散的其它机制而降低最终产品的所需芳香或香味性能。因此,给定芳香或香料组合物中的芳香和香料成分各自的量可基于所选择的成分的芳香和/或香味特性、产品的总体组成和意欲芳香和/或香味效果而选择。
添加剂可用于本申请的香料和芳香组合物中。可使用的添加剂包括但不限于溶剂和表面活性剂。其它芳香和香料组合物添加剂可根据组合物的意欲用途选择。
可用于本申请的香料和芳香组合物中的溶剂,例如水溶性有机溶剂包括但不限于乙醇、丙醇、异丙醇、丁醇、3-甲氧基-3-甲基-1-丁醇、苄纯、乙基甲醇(二甘醇单***)、乙二醇、丙二醇、二丙二醇、丁二醇、己二醇、甘油、乙二醇单甲醚、丙二醇单甲醚、丙二醇单***和二丙二醇单甲醚。这些水溶性溶剂可单独或者组合使用。本申请的组合物中的水溶性有机溶剂含量可根据所需组合物性能确定,且通常为约1%至约99质量%。在一个实施方案中,水溶性溶剂的含量为约1%至约10质量%、约5%至约15质量%、约10%至约20质量%、约15%至约25质量%、约20%至约30质量%、约25%至约35质量%、约30%至约40质量%、约35%至约45质量%、约40%至约50质量%、约45%至约55质量%、约50%至约60质量%、约55%至约65质量%、约60%至约70质量%、约75%至约85质量%、约80%至约90质量%、约85%至约95质量%、约90%至约99质量%,或者约95%至约99质量%。在一个实施方案中,水溶性溶剂的含量为99质量%、98质量%、97质量%、96质量%、95质量%、94质量%、93质量%、92质量%、91质量%、90质量%、85质量%、80质量%、75质量%、70质量%、65质量%、60质量%、55质量%、50质量%、45质量%、40质量%、35质量%、30质量%、25质量%、20质量%、15质量%、10质量%、9质量%、8质量%、7质量%、6质量%、5质量%、4质量%、3质量%、2质量%,或者1质量%。
可用于本申请的香料和芳香组合物中的油溶性有机溶剂包括但不限于异链烷烃、链烷烃、柠檬油精、松萜、柠檬酸三乙酯、苯甲酸苄基酯、肉豆蔻酸异丙酯、醋精和硅。
优选的溶剂包括但不限于柠檬酸三乙酯、醋精、甘油、乙醇、水、甘油三酯、液体蜡、丙二醇衍生物和乙二醇衍生物。
本申请的香料和芳香组合物可与其它物质组合使用,包括但不限于多价螯合剂、防腐剂、抗氧化剂、除臭剂、消毒剂、紫外线吸收剂、pH调节剂、杀虫组分、保护以防昆虫的组分、昆虫驱避剂、着色剂、赋形剂和缓冲剂。用于本申请的芳香和香料组合物中或者除本申请的芳香和香料组合物外使用的物质可由包含组合物的产品决定。当物质用于香料或芳香组合物中时,它可以为添加剂。当物质与香料或芳香组合物一起使用时,可认为它是包含芳香或香料组合物的产品组合物的一部分。
可用于本发明的芳香或加香组合物中的赋形剂可取决于意欲产品的用途及其总体组成而变化。在一些情况下,赋形剂可包含在芳香或香料组合物中,或者作为选择,可独立于组合物。用于口服药物的加香组合物中或者与口服药物的加香组合物一起使用的赋形剂包括但不限于片剂涂料,例如纤维素醚羟丙基甲基纤维素、合成聚合物、虫漆、玉米蛋白或其它多糖,和明胶。在宠物垫材中,可使用包含含纤维素或叶绿素的试剂或者其它材料的固体赋形剂。相反,化妆品赋形剂可包括但不限于carbopol 940 ETD、三乙醇胺、纯净水、甘油、咪唑烷基脲、EDTA,1聚乙烯醇、羟苯甲酯、苯氧基乙醇0、乙醇1、peg 7甘油椰油酸酯、peg6三甘油基己酸甘油酯、acemulogar LAM V、肉豆蔻酸异丙酯、tegosoft CT、zantham树胶、sepicide CL、聚季铵盐7和凡士林油。与香料和/或芳香组合物一起或者在香料和/或芳香组合物中用于给定产品的其它合适赋形剂可由本领域技术人员容易地选择。
可与本申请的芳香和加香组合物一起使用的缓冲剂可取决于意欲产品的用途及其总体组成而变化。在一些情况下,缓冲剂可包含在芳香或香料组合物中,或者作为选择可独立于组合物。可用于本申请的芳香和香料组合物中或者与本申请的芳香和香料组合物一起使用的缓冲剂的实例包括但不限于柠檬酸盐、乙酸盐和磷酸盐。例如,柠檬酸三钠可用作香料或防腐剂,并且已知赋予香料酸味,而且充当缓冲剂。柠檬酸三钠为多种碳酸水和其它饮料以及饮用混合料和德国式小香肠中的成分。在化妆品中,磷酸氢二钠、磷酸二氢钾、磷酸氢二钠和柠檬酸可用于缓冲产品的pH。在牙膏中,碳酸钙和/或磷酸二钙可用作pH缓冲剂。与香料和/或芳香组合物一起或者在香料和/或芳香组合物中用于给定产品的其它合适缓冲剂可由本领域技术人员容易地选择。
本申请的芳香和香料组合物可包含浓度范围的新戊二醇二乙酸酯,例如在一个实施方案中,约0.0005%至约99.9质量%新戊二醇二乙酸酯,与约99.9995%至约0.1质量%的一种或多种添加剂和/或其它芳香或香料成分。在一个实施方案中,包含约0.5%至约50质量%新戊二醇二乙酸酯的芳香或香料组合物可与约99.5%至约50质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约0.5%至约10质量%新戊二醇二乙酸酯的芳香或香料组合物可与约99.5%至约90质量%的一种或多种添加剂和/或芳香或香料成分组合。在一个实施方案中,包含约10%至约20质量%新戊二醇二乙酸酯的芳香或香料组合物可与约90%至约80质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约20%至约30质量%新戊二醇二乙酸酯的芳香或香料组合物可与约80%至约70质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约30%至约40质量%新戊二醇二乙酸酯的芳香或香料组合物可与约70%至约60质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约40%至约50质量%新戊二醇二乙酸酯的芳香或香料组合物可与约60%至约50质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约50%至约60质量%新戊二醇二乙酸酯的芳香或香料组合物可与约50%至约40质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约60%至约70质量%新戊二醇二乙酸酯的芳香或香料组合物可与约40%至约30质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约70%至约80质量%新戊二醇二乙酸酯的芳香或香料组合物可与约30%至约20质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约80%至约90质量%新戊二醇二乙酸酯的芳香或香料组合物可与约20%至约10质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约85%至约95质量%新戊二醇二乙酸酯的芳香或香料组合物可与约15%至约5质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约90%至约99.5质量%新戊二醇二乙酸酯的芳香或香料组合物可与约10%至约0.5质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约90%至约98质量%新戊二醇二乙酸酯的芳香或香料组合物可与约10%至约8质量%的一种或多种添加剂和/或其它芳香或香料成分组合。在一个实施方案中,包含约90%至约95质量%新戊二醇二乙酸酯的芳香或香料组合物可与约10%至约5质量%的一种或多种添加剂和/或其它芳香或香料成分组合。
这些和其它实施方案的功能和优点从以下非限定性实施例中更完整地理解。实施例在性质上意欲为说明性的,且不认为限制本文所述实施方案的范围。
实施例
实施例1:新戊二醇二乙酸酯的合成
化合物 | MW | 质量/体积 | 摩尔数 |
新戊二醇 | 104.15 | 26.0g | 0.25 |
乙酸酐 | 102.09 | 57.3g | 0.55 |
N,N’-二甲基氨基吡啶 | 122.17 | 0.916g | 0.0075 |
四氢呋喃 | 100ml |
经20分钟的过程将乙酸酐缓慢加入新戊二醇(0.25摩尔)、N,N’-二甲基氨基吡啶(0.0075摩尔)和四氢呋喃(100ml)的搅拌溶液中。观察到放热。将反应混合物搅拌整夜。GCMS显示出原料完全转化成所需产物。将20ml水缓慢加入反应混合物中,然后将混合物在降低的压力下放在旋转式蒸发器上以除去四氢呋喃溶剂。将所得液体溶于乙酸乙酯(200ml)中,用10重量%碳酸钠水溶液(200ml)洗涤,其后用盐水(200ml)洗涤。然后在旋转式蒸发器上在降低的压力下除去乙酸乙酯以得到48g粗产物。然后将粗产物在1.27毫巴和65℃下蒸馏。在第一馏分中收集3.3g产物,在第二馏分中收集14.5g产物,并且在第三馏分中收集14.6g产物。发现第二和第三馏分具有对感官评估而言足够的非常高的纯度(>99%,通过GC-FID)。图1显示通本文所述方法制备的新戊二醇二乙酸酯的纯度分析。
通过本文所述方法制备的新戊二醇二乙酸酯的1H NMR(400MHz,CDCl3)谱具有以下峰的化学位移值(ppm):δ0.96(d,J=0.8Hz,6H,-CH3),2.06(m,J=0.8Hz,6H,-CH3),3.87(s,4H,-CH2-)。
图2显示通过本文所述方法制备的新戊二醇二乙酸酯的13C NMR(125MHz,CDCl3)谱。光谱中峰的化学位移值(ppm)为:δ20.7(2C,R-CH3),21.6(2C,-CO-CH3),34.4(1C,C),69.0(2C,C-CH2-O)和170.8(2C,-C=O)。
实施例2:用于气味检测的气相色谱仪的校准
气味检测阈值可使用气相色谱仪测定。使用已知浓度和链长分布的烃标准将气相色谱仪校准以容许测定通过注射器注入的材料的确切体积、精确的分离比和烃响应。测量空气流速并基于12秒的人吸入的消耗持续时间计算取样的体积。由于在任何时间点检测器处的精确浓度可如上所述测定,可计算吸入的单位体积质量,因此计算测试材料的浓度。为测定材料是否具有50ppb以下的可检测气味阈值,将溶液以使用上述方法计算的浓度输送至吸入口。随后,试验人员吸入来自气相色谱仪的流出物并确定注意到气味时的停留时间。来自所有试验人员的平均数据得到值得注意的阈值。
将计算量的分析物注入气相色谱仪柱中以实现检测器处50ppb的浓度。用于借助该方法测定气味检测阈值的典型气相色谱仪参数列于下面。
·GC:具有FID检测器的5890II系列
·7673自动取样器
·柱:J&W Scientific DB-1
·长30米ID 0.25mm膜厚度1μm
·方法:
·分离注射:17/1分离比
·自动取样器:每次注射1.13μl
·柱流量:1.10mL/分钟
·空气流量:345mL/分钟
·入口温度:245℃
·检测器温度:285℃
·温度信息
·初始温度:50℃
·速率:5℃/分钟
·最终温度:280℃
·最终时间:6分钟
·主要假设:
ο(i)每次吸入12秒
ο(ii)GC空气增加试样稀释
实施例3:新戊二醇二乙酸酯的嗅觉分析
将通过实施例1的方法制备的含水新戊二醇二乙酸酯取样到芳香吸纸上以评估化合物的芳香。
新戊二醇二乙酸酯首先纯净地呈现于吸纸上。发现具有甜且描述为清新、果味、树脂和没药状的芳香,具有脂肪香。
然后制备通过实施例1的方法合成的新戊二醇二乙酸酯在柠檬酸三乙酯中的10%稀释物,并取样到吸纸上。10%稀释物产生类似的肯定芳香。吸纸上的香气持久力为约5-10小时。
新戊二醇二乙酸酯的嗅觉分析证明该化合物可用于赋予芳香和香料组合物理想的芳香。
现在描述了本申请的一些实施方案,本领域技术人员应当了解上述仅为说明性且不是限定性的,仅通过实施例呈现。因此,本申请的实施方案可以为其它具体形式而不偏离其精神或基本特性。
仅使用例行实验,本领域技术人员应当认识到或者能够确定本申请具体实施方案的等效物。因此,应当理解本文所述实施方案仅通过实施例呈现且本申请的范围因此由所附权利要求书及其等效物说明,并且本申请可不同于如上述说明书中具体描述的实践。
当用于描述本申请的一种组合物时,术语“约”指所述百分数±5%、±4%、±3%、±2.5%、±2%、±1.5%、±1%、±0.75%、±0.5%、±0.25%,或者±0.1%。在一个实施方案中,术语“约”指所述百分数±5%。例如,“约50%”指范围45%至55%。在一个实施方案中,术语“约”指所述百分数±2.5%。在一个实施方案中,术语“约”指所述百分数±1%。在一个实施方案中,术语“约”指所述百分数±0.5%。在一个实施方案中,术语“约”指所述百分数±0.1%。
如本文所用,除非上下文另外明确说明,单数形式“一个/一种(a/an)”和“该(the)”包括复数指示物。因此,例如,对“芳香成分”的提及不仅包括单一芳香成分,而且包括两种或更多种芳香成分的组合或混合物,对“添加剂”的提及包括单一添加剂以及两种或更多种添加剂,等等。
如本文所用,短语“例如”或“包括”意指介绍进一步阐明更一般的主题的实例。这些实例仅作为帮助理解公开内容而提供,且不意指以任何方式限定。此外,如本文所用,术语“可”、“任选”、“任选地”或“可任选”意指随后描述的情形可能发生或可能不发生,使得该描述包括该情形发生的情况和它不发生的情况。例如,短语“任选存在”意指物体可存在或可能不存在,因此,该描述包括存在该物体的情况和不存在该物体的情况。
通过引用将本文提及的各专利文件和科学文章关于所有目的的全部公开内容全部结合到本文中。
Claims (27)
1.一种芳香组合物,其包含新戊二醇二乙酸酯。
2.根据权利要求1的芳香组合物,其中新戊二醇二乙酸酯赋予芳香组合物香味。
3.根据权利要求2的芳香组合物,其进一步包含一种或多种添加剂、一种或多种芳香成分,或者其组合。
4.根据权利要求3的芳香组合物,其中芳香组合物包含至少一种添加剂。
5.根据权利要求4的芳香组合物,其中至少一种添加剂包含表面活性剂。
6.根据权利要求3的芳香组合物,其中组合物包含至少一种芳香成分。
7.根据权利要求6的芳香组合物,其中至少一种芳香成分包含油。
8.根据权利要求2的芳香组合物,其中芳香组合物包含至少一种添加剂和至少一种芳香成分。
9.根据权利要求4的芳香组合物,其中所述至少一种添加剂为溶剂。
10.根据权利要求9的芳香组合物,其中所述溶剂为柠檬酸三乙酯。
11.根据权利要求9的芳香组合物,其中在组合物中新戊二醇二乙酸酯的浓度为组合物的0.5%至10质量%。
12.根据权利要求10的芳香组合物,其中芳香组合物为新戊二醇二乙酸酯在柠檬酸三乙酯中的10%稀释物。
13.根据权利要求1-12中任一项的芳香组合物,其用于香料、空气清新剂、衣物洗涤剂、家用清洁产品、液体或条皂、洗发水、护发素、发用喷雾、化妆品、除臭剂、昆虫驱避剂、杀虫剂或宠物垫材中。
14.根据权利要求1-12中任一项的芳香组合物,其中芳香组合物为清洁组合物、油漆组合物、空气清新剂组合物、脱脂组合物或涂料组合物。
15.一种香料组合物,其包含新戊二醇二乙酸酯。
16.根据权利要求15的香料组合物,其中新戊二醇二乙酸酯赋予香料组合物香味。
17.根据权利要求16的香料组合物,其进一步包含至少一种添加剂、至少一种香料成分,或者其组合。
18.根据权利要求17的香料组合物,其包含至少一种添加剂。
19.根据权利要求18的香料组合物,其中至少一种添加剂包含表面活性剂。
20.根据权利要求17的香料组合物,其包含至少一种香料成分。
21.根据权利要求20的香料组合物,其中至少一种香料成分包含油。
22.根据权利要求17的香料组合物,其包含至少一种添加剂和至少一种香料成分。
23.根据权利要求18的香料组合物,其中所述至少一种添加剂为溶剂。
24.根据权利要求23的香料组合物,其中所述溶剂为柠檬酸三乙酯。
25.根据权利要求23的香料组合物,其中在组合物中新戊二醇二乙酸酯的浓度为组合物的0.5%至10质量%。
26.根据权利要求24的香料组合物,其中芳香组合物为新戊二醇二乙酸酯在柠檬酸三乙酯中的10%稀释物。
27.根据权利要求15-26中任一项的香料组合物,其用于牙膏、漱口水、口服药物,或者食品中。
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EP3822250B1 (en) * | 2018-07-13 | 2022-08-31 | Mitsubishi Gas Chemical Company, Inc. | Carboxylic ester compound, production method therefor, composition, and perfume composition |
JP7408674B2 (ja) | 2019-02-25 | 2024-01-05 | ビーエーエスエフ ソシエタス・ヨーロピア | (3-ヒドロキシ-2,2-ジメチル-プロピル)アセテートと組み合わせた(3-アセトキシ-2,2-ジメチル-プロピル)アセテートの香料としての使用 |
CN114269888A (zh) * | 2019-06-20 | 2022-04-01 | 阿尔门德拉私人有限公司 | 香气增强组合物 |
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DE2017208A1 (de) | 1970-04-10 | 1971-10-21 | Haarmann & Reimer GmbH, 3450 Holz minden | 4-Methy l-pentanoI-2-crotonat |
US4017537A (en) | 1975-08-25 | 1977-04-12 | Eastman Kodak Company | Noncatalyzed aldol reaction |
JPS55136249A (en) | 1979-04-09 | 1980-10-23 | T Hasegawa Co Ltd | Alkyl 3-alkylcarbonyl oxy-cis (or trans)-5-octenoate, its preparation and use |
US4368145A (en) | 1981-10-01 | 1983-01-11 | International Flavors & Fragrances, Inc. | Perfume use for oxoalkyl esters |
US4498996A (en) * | 1982-07-08 | 1985-02-12 | International Flavors & Fragrances Inc. | Use in augmenting or enhancing aroma of perfumed article with acyloxy alkanols and esters thereof |
JPH09255986A (ja) * | 1996-03-25 | 1997-09-30 | Shiseido Co Ltd | 香料含有水系組成物 |
FI970269A (fi) | 1997-01-22 | 1998-07-23 | Neste Oy | 1,3-diolipohjaisten esterien seokset, menetelmä 1,3-diolipohjaisten esterien valmistamiseksi sekä esterien käyttö |
US6280519B1 (en) | 1998-05-05 | 2001-08-28 | Exxon Chemical Patents Inc. | Environmentally preferred fluids and fluid blends |
US6818049B1 (en) * | 1998-05-05 | 2004-11-16 | Exxonmobil Chemical Patents Inc. | Environmentally preferred fluids and fluid blends |
JP3589914B2 (ja) * | 1998-12-21 | 2004-11-17 | 花王株式会社 | 香料粒子組成物 |
DE10034729A1 (de) | 2000-07-17 | 2002-02-28 | Nikolaus Theres | Regulatorische Sequenzen aus meristematischen Zellen |
CA2900181C (en) * | 2003-08-06 | 2019-01-29 | Catherine Tachdjian | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
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2016
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- 2016-01-22 EP EP16740848.3A patent/EP3247691B1/en active Active
- 2016-01-22 MY MYPI2017702669A patent/MY181719A/en unknown
- 2016-01-22 CA CA2974102A patent/CA2974102C/en active Active
- 2016-01-22 CN CN202210930929.9A patent/CN115418269A/zh active Pending
- 2016-01-22 ES ES16740848T patent/ES2836277T3/es active Active
- 2016-01-22 WO PCT/US2016/014557 patent/WO2016118882A1/en active Application Filing
- 2016-01-22 JP JP2017558346A patent/JP6703550B2/ja active Active
- 2016-01-22 PL PL16740848T patent/PL3247691T3/pl unknown
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2017
- 2017-07-20 US US15/655,374 patent/US10072233B2/en active Active
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- 2018-04-23 HK HK18105257.7A patent/HK1245760A1/zh unknown
- 2018-05-28 HK HK18106921.1A patent/HK1247186A1/zh unknown
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WO2016118882A1 (en) | 2016-07-28 |
BR112017015827A2 (pt) | 2018-03-27 |
BR112017015827B1 (pt) | 2022-05-10 |
EP3247691A1 (en) | 2017-11-29 |
EP3247691B1 (en) | 2020-09-16 |
CA2974102A1 (en) | 2016-07-28 |
CN107428638B (zh) | 2023-01-24 |
MY181719A (en) | 2021-01-05 |
US10072233B2 (en) | 2018-09-11 |
US20180037844A1 (en) | 2018-02-08 |
JP6703550B2 (ja) | 2020-06-03 |
HK1245760A1 (zh) | 2018-08-31 |
PL3247691T3 (pl) | 2021-03-08 |
WO2016118882A8 (en) | 2016-12-22 |
EP3247691A4 (en) | 2018-08-08 |
ES2836277T3 (es) | 2021-06-24 |
HK1247186A1 (zh) | 2018-09-21 |
JP2018510954A (ja) | 2018-04-19 |
CN107428638A (zh) | 2017-12-01 |
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