CN107915625B - 一种降龙涎薄荷酯香料 - Google Patents

一种降龙涎薄荷酯香料 Download PDF

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CN107915625B
CN107915625B CN201610882201.8A CN201610882201A CN107915625B CN 107915625 B CN107915625 B CN 107915625B CN 201610882201 A CN201610882201 A CN 201610882201A CN 107915625 B CN107915625 B CN 107915625B
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fragrance
ambroxol
ambergris
spice
products
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CN107915625A (zh
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杨绍祥
田红玉
刘永国
陈海涛
孙宝国
李丽慧
郝颜峰
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Beijing Technology and Business University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • 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
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof

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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Fats And Perfumes (AREA)
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Abstract

本发明公开了一种新型化合物降龙涎薄荷酯，具体化学结构式如下所示：

Description

一种降龙涎薄荷酯香料
技术领域
本发明涉及一种新型芳香化合物，它适于在香精、化妆品、洗涤用品等产品中产生香气。
背景技术
在香料工业中越来越要求提供一种新的化合物，使调香师能够以其作为香原料，为香精、化妆品、洗涤用品制造新香味。
降龙涎薄荷酯作为降龙涎二醇及薄荷醇的衍生物，与香紫苏内酯具有类似的结构。香紫苏内酯天然存在于雪茄和东方型香料烟中，是一种优良的烟草增香矫味剂，可以改进和提高烟草香味质量，使其更加柔和、醇绵；能够增大和提高食品的感官，可用于含有甜味佐料的食品中，增加食品的嗅觉效果；可以加重咖啡苦味，提高咖啡的提神效果。在没有心血管刺激作用情况下，当减少身体脂肪时，香紫苏内酯能够帮助增进变瘦身体的质量。因此，可广泛用于减肥产品；降龙涎二醇，又名香紫苏二醇，具有类似龙涎香香气，持久的木香香气，可作为调配日用香精的定香剂；薄荷醇具有特征的薄荷香气并有清凉的作用，有止痒、止痛、防腐、刺激、麻醉、清凉和抗炎作用，可治头痛、神经痛、瘙痒等作用。
Figure BSA0000135126600000011
尽管降龙涎二醇及香紫苏内酯已经被广泛应用，仍需提供其他新的化学试剂，使香料商为各种应用制造新的香味，满足人们对新香味日益增长的需求。
发明内容
本发明目的是提供一种新型化合物，它适于在香精、化妆品、洗涤用品等产品中产生香气。
更具体的是，本发明涉及新型化合物降龙涎薄荷酯，它通过以下通式表示：
Figure BSA0000135126600000012
具体实施方式
实施例1.降龙涎薄荷酯的制备
合成路线如下式所示：
Figure BSA0000135126600000021
将1.55g(5mmol)A乙酰羟基降龙涎酸与0.94g(6mmol)B薄荷醇加入到50mL三口烧瓶中，再称取1.15g(6mmol)1-(3-二甲氨基丙基)-3-乙基碳二亚胺(EDCI)与0.12g(1mmol)4-二甲氨基吡啶(DMAP)加入到其中，加入20mL二氯甲烷，加热到40℃回流搅拌48h。后将温度将至室温，加入12mL 10％H2SO4溶液，分液，有机相依次用适量饱和NaHCO3、饱和NaCl溶液洗涤，旋蒸，柱层析分离纯化(石油醚∶乙酸乙酯＝15∶1)，得白色晶体0.82g，产率37.0％。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(300MHz，CDCl3)δ：0.73(3H，s，Me-19)，0.75(3H，s，Me-19)，0.78(6H，s，2Me-4)，2.71(H，m，H-9)，4.66(H，m，H-13)。
13C NMR(75MHz，CDCl3)δ：15.41，15.99，18.04，19.77，20.07，20.73，21.29，21.71，21.92，23.15，26.04，30.77，31.25，32.93，33.14，34.14，38.67，40.82，41.51，47.01，48.42，54.29，55.04，74.00，86.06，170.01，173.69。
实施例2.香气评价
分别取0.01g降龙涎薄荷酯、降龙涎二醇、薄荷醇、香紫苏内酯样品配制为10％丙二醇溶液，用评香条沾取少量溶液，在无其他气味干扰的情况下嗅闻评香条上的气味，进行香气评价。
降龙涎薄荷酯样品具有清甜香、奶味；降龙涎二醇具有较轻的甜香，淡奶香味，淡木香；薄荷醇具有薄荷香气；香紫苏内酯具有淡木香。
降龙涎薄荷酯具有区别于降龙涎二醇、薄荷醇及香紫苏内酯的香气特征。

Claims (1)

1.一种芳香化合物降龙涎薄荷酯，其特征在于，具体化学结构式如下所示：
Figure FFW0000021584970000011
CN201610882201.8A 2016-10-10 2016-10-10 一种降龙涎薄荷酯香料 Expired - Fee Related CN107915625B (zh)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105296157A (zh) * 2015-12-03 2016-02-03 北京工商大学 一种降龙涎紫苏酯香料

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105296157A (zh) * 2015-12-03 2016-02-03 北京工商大学 一种降龙涎紫苏酯香料

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