CN113801106A - 一种γ-己内酯潜香化合物、制备方法及用途 - Google Patents
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/08—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
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- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
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- A24B3/12—Steaming, curing, or flavouring tobacco
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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Abstract
本发明公开了一种γ‑己内酯潜香化合物、制备方法及用途,将γ‑己内酯溶解于足量溶剂中,在‑78℃~50℃温度条件下加入碱,搅拌反应20min以上,然后加入2‑乙酰基吡啶,继续在‑78℃~50℃温度条件下搅拌反应30min以上,接着淬灭反应,最后进行后处理分离纯化得到目标内酯潜香化合物。本发明的潜香化合物具有常温环境下性质稳定,在加热条件下能够均匀释放香味的特性,同时还可增加和丰富内酯香料的种类、拓宽内酯香原料及酰基吡啶的应用范围,还可克服降内酯及酰基吡啶自身的缺陷,如:挥发性高、阈值小、闻香重、加工过程易损失等。
Description
技术领域
本发明涉及烟草香精技术领域,尤其涉及一种γ-己内酯潜香化合物、制备方法及用途。
背景技术
γ-己内酯(FEMA#2556,CAS#695-06-7),具有类似香豆素的特点,却不需要触碰香豆素引来的法律法规风险,具有甜的乳脂、乳糖香味和烟草、香豆素、椰子香味,常用于配制豆香、奶香烟用香精,用以提高烟气浓度,增加烟草豆甜香、奶香香韵。吡啶类化合物,是烟用香精领域杂环类化合物中开发应用最广的化合物之一,2-乙酰基吡啶具有爆米花、坚果香样的香气,还有烟草的特征香气,常用于调配烘烤香、奶香烟用香精,用增加坚果香、烘烤、焦甜香韵,提高烟气浓度。
然而上述两种分子都具有挥发性较、阈值低的特点,其直接运用于烟草配方中会带来易挥发、含量不稳定的缺点,影响烟草制品的品质稳定性。
潜香物质,又称为香料前体,是指通过物理或化学的手段,将一种或以上挥发性高或易升华的香料合成出该香料的前体。香料前体本身没有香气或香气不明显,在常温下挥发性弱、化学性质温度,能够长时间保存,只有在烟草制品燃烧或加热的状态下才会释放出期望的香味成分,从而达到烟草制品增香的目的。通过香料前体加香,可以在赋予烟草制品独特的风格特色的同时,减少香料在加工和储存过程中的损失,在降低香料使用成本、改善烟草制品稳定性方面有重要作用。
发明内容
本发明的目的就在于为了解决上述问题而提供一种γ-己内酯潜香化合物、制备方法及用途,本发明基于γ-己内酯和烘烤香韵酰基吡啶共价相连制备出新型潜香化合物,具有稳定性高,耐加工性强的特点,能够克服γ-己内酯及酰基吡啶的挥发性高、阈值小、闻香重、加工过程易损失等缺点。同时在高温(抽吸条件下)能够裂解释放出γ-己内酯和酰基吡啶等香味物质,用于改善卷烟的抽吸品质,彰显卷烟风格。
本发明通过以下技术方案来实现上述目的:
一种γ-己内酯潜香化合物,其结构式如下:
本发明另一方面还提供了一种γ-己内酯潜香化合物的制备方法,制备反应式如下:
具体制备方法为:将γ-己内酯溶解于足量溶剂中,在-78℃~50℃温度条件下加入碱,搅拌反应20min以上,然后加入2-乙酰基吡啶,继续在-78℃~50℃温度条件下搅拌反应30min以上,接着淬灭反应,最后进行后处理分离纯化得到目标内酯潜香化合物。
进一步方案为,所述溶剂为乙醚、甲基叔丁基醚、四氢呋喃、二氧六环、甲基四氢呋喃、二氯甲烷、1,2-二氯乙烷、二甲基亚砜、石油醚中的一种或多种。
进一步方案为,所述碱为BuLi、LDA、LiHMDS、NaNH2、NaH、NaOC(CH3)3、KOC(CH3)3、NaOEt或KOEt中的一种或多种。
进一步方案为,所述γ-己内酯、碱和2-乙酰基吡啶的摩尔比为1∶(4~6)∶(1~1.5)。
进一步方案为,所述淬灭反应及后处理是指用水淬灭反应,分出有机层,再饱和食盐水洗涤、无水硫酸钠干燥、过滤、减压蒸馏去除溶剂,得到的残余物用硅胶柱层析分离。
进一步方案为,所述反应温度为-70℃~0℃;第一次搅拌的时间在20~60min;第二次搅拌的时间在30min~12h。
本发明又一方面还提供了上述的潜香化合物、上述的制备方法制备的潜香化合物作为香料的用途,具体为将潜香化合物按照重量0.00001%~10%的添加比例添加到燃烧或者加热过程释放香味的产品中,如用于生产特定香韵的熏香、蜡烛或壁炉燃料,或特殊风味的调料汁、卤料或植物油中,或其它在燃烧或加热时释放出风味物质如烟草。
本发明再一方面还提供了上述的潜香化合物、上述的制备方法制备的潜香化合物在烟草中的用途,具体为将潜香化合物以烟草重量0.00001%~2%的添加比例添加到烟草中。
进一步方案为,所述潜香化合物添加到烟草中的加入方法为加表香、加料香或薄片加香;或将潜香化合物溶于水、醇或者二者的混合溶剂中,然后将溶液喷洒或者注射到烟草上;所述烟草是混合型或者烤烟型的成品,或者是成品配方的组成部分。
本发明的有益效果在于:
本发明的潜香化合物具有常温环境下性质稳定,在加热条件下能够均匀释放香味的特性同时还可增加和丰富内酯香料的种类、拓宽内酯香原料及酰基吡啶的应用范围,还可克服降内酯及酰基吡啶自身的缺陷,如:挥发性高、阈值小、闻香重、加工过程易损失等。
附图说明
为了更清楚地说明本发明实施例中的技术方案,下面将对实施例或现有技术描述中所需要实用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的一些实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据这些附图获得其他的附图。
图1为本发明潜香化合物LSD8的1H NMR核磁谱图。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚,下面将对本发明的技术方案进行详细的描述。显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动的前提下所得到的所有其它实施方式,都属于本发明所保护的范围。
实施例1
将25ml(50mmol)的二异丙基氨基锂置于圆底烧瓶中,在-60℃搅拌20分钟,然后将1.1g(10mmol)γ-己内酯溶解于10ml无水四氢呋喃,缓慢滴加到二异丙基氨基锂溶液中,在-60℃搅拌30分钟。将1.21克(10mmol)2-乙酰基吡啶溶解于20ml无水四氢呋喃,缓慢滴加到以上反应体系中,在-60℃搅拌40分钟后,加入30ml水猝灭。浓缩除去四氢呋喃,加入100ml二氯甲烷萃取,有机层用饱和盐水洗涤,并用无水硫酸钠干燥。在减压下蒸发溶剂,得到固体,将其通过柱色谱纯化,得到目标化合物1.65g(NZ1),收率70%。
测试结果如图1所示,其中结构表征如下:
1HNMR(400MHz,CDCl3):δ,ppm 0.80~0.87(m,3H),1.37~1.64(m,3H),1.65~1.82(m,3H),1.84~2.00(m,1H),2.97~3.28(m,1H),4.07~4.49(m,1H),4.60~5.68(m,1H),7.13~7.19(m,1H),7.31~7.50(m,1H),7.56~7.75(m,1H),8.42~8.46(m,1H)。
实施例2
现以NZ1卷烟加香评吸实验来说明这类化合物改善卷烟烟气香气。称取一定量的NZ1用乙醇溶解后,按0.003%添加于某烤烟型烟丝上,卷制成实验卷烟。用同样的烟丝,添加与上面同样比例的乙醇,卷制成空白样卷烟。对比评吸表明,与对照样比较,实验卷烟有较明显的甜香、豆香香韵及烘烤香韵,具有增浓增厚的作用。
综上所述,本发明的新型潜香化合物在卷烟燃烧时可均匀地向卷烟烟气释放降γ-己内酯及酰基吡啶,该类潜香化合物具沸点高、挥发性低、闻香轻等优点,用于卷烟加香有很好的烟气增香效果。由此可知,本发明向卷烟中加入潜香化合物在卷烟中释放相应具有特定香韵,同时还克服了γ-己内酯及酰基吡啶自身的如挥发性高、阈值小、闻香重,加工过程易损失等缺陷。
以上所述,仅为本发明的具体实施方式,但本发明的保护范围并不局限于此,任何熟悉本技术领域的技术人员在本发明揭露的技术范围内,可轻易想到变化或替换,都应涵盖在本发明的保护范围之内。因此,本发明的保护范围应以所述权利要求的保护范围为准。另外需要说明的是,在上述具体实施方式中所描述的各个具体技术特征,在不矛盾的情况下,可以通过任何合适的方式进行组合,为了避免不必要的重复,本发明对各种可能的组合方式不再另行说明。此外,本发明的各种不同的实施方式之间也可以进行任意组合,只要其不违背本发明的思想,其同样应当视为本发明所公开的内容。
Claims (10)
3.如权利要求2所述的一种γ-己内酯潜香化合物的制备方法,其特征在于,所述溶剂为乙醚、甲基叔丁基醚、四氢呋喃、二氧六环、甲基四氢呋喃、二氯甲烷、1,2-二氯乙烷、二甲基亚砜、石油醚中的一种或多种。
4.如权利要求2所述的一种γ-己内酯潜香化合物的制备方法,其特征在于,所述碱为BuLi、LDA、LiHMDS、NaNH2、NaH、NaOC(CH3)3、KOC(CH3)3、NaOEt或KOEt中的一种或多种。
5.如权利要求2所述的一种γ-己内酯潜香化合物的制备方法,其特征在于,所述γ-己内酯、碱和2-乙酰基吡啶的摩尔比为1:(4~6):(1~1.5)。
6.如权利要求2所述的一种γ-己内酯潜香化合物的制备方法,其特征在于,所述淬灭反应及后处理是指用水淬灭反应,分出有机层,再饱和食盐水洗涤、无水硫酸钠干燥、过滤、减压蒸馏去除溶剂,得到的残余物用硅胶柱层析分离。
7.如权利要求2所述的一种γ-己内酯潜香化合物的制备方法,其特征在于,所述反应温度为-70℃~0℃;第一次搅拌的时间在20~60min;第二次搅拌的时间在30min~12h。
8.如权利要求1所述的潜香化合物、2-7所述的制备方法制备的潜香化合物作为香料的用途,具体为将潜香化合物按照重量0.00001%~10%的添加比例添加到燃烧或者加热过程释放香味的产品中。
9.如权利要求1所述的潜香化合物、2-7所述的制备方法制备的潜香化合物在烟草中的用途,具体为将潜香化合物以烟草重量0.00001%~2%的添加比例添加到烟草中。
10.根据权利要求9所述的潜香化合物的用途方法,其特征在于所述潜香化合物添加到烟草中的加入方法为加表香、加料香或薄片加香;或将潜香化合物溶于水、醇或者二者的混合溶剂中,然后将溶液喷洒或者注射到烟草上;所述烟草是混合型或者烤烟型的成品,或者是成品配方的组成部分。
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CN105061407A (zh) * | 2015-07-16 | 2015-11-18 | 川渝中烟工业有限责任公司 | 基于降龙涎香内酯的潜香化合物及其制备方法和应用 |
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WO1992009590A1 (en) * | 1990-11-29 | 1992-06-11 | Henkel Corporation | PROCESS FOR THE PREPARATION OF α-ALKYL LACTONES |
CN105061407A (zh) * | 2015-07-16 | 2015-11-18 | 川渝中烟工业有限责任公司 | 基于降龙涎香内酯的潜香化合物及其制备方法和应用 |
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