CN111517959B - 一种紫苏醇香叶醇碳酸酯香料 - Google Patents

一种紫苏醇香叶醇碳酸酯香料 Download PDF

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CN111517959B
CN111517959B CN201910038744.5A CN201910038744A CN111517959B CN 111517959 B CN111517959 B CN 111517959B CN 201910038744 A CN201910038744 A CN 201910038744A CN 111517959 B CN111517959 B CN 111517959B
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alcohol
carbonate
perilla
spice
fragrance
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CN111517959A (zh
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杨绍祥
田红玉
刘永国
梁森
孙宝国
王皓
戴慧康
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Shenzhen Chengze Information Technology Co ltd
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Beijing Technology and Business University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
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Abstract

本发明公开了一种化合物紫苏醇香叶醇碳酸酯，具体化学结构式如下所示：

Description

一种紫苏醇香叶醇碳酸酯香料
技术领域
本发明涉及一种芳香化合物，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
在香料工业种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。
碳酸酯类化合物是一类重要的香料，现已广泛用于各种食品饮料等食用香精的配方中，到目前为止已有三种碳酸酯类香料被批准为可食用香料，分别为1-薄荷醇丙二醇碳酸酯(FEMA号为3806)，无色液体具有薄荷样的凉味；1-薄荷醇乙二醇碳酸酯(FEMA号为3805)，无色液体，具有薄荷样的凉味；d1-薄荷脑(+/-)-1，2-丙二醇碳酸酯(FEMA号为3992)，无色清凉液体，具有薄荷香气，主要用于焙烤食品，饮料、奶酪、口香糖、调味料等食品的加香。
尽管部分碳酸酯类香料已经被广泛应用，仍需提供其他新的香料化合物，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，本发明涉及化合物紫苏醇香叶醇碳酸酯，它通过以下通式表示：
Figure BSA0000177717800000011
具体实施方式
实施例1.紫苏醇香叶醇碳酸酯的制备
合成路线如下式所示：
Figure BSA0000177717800000012
将1.52g(10mmol)紫苏醇，4.86g(30mmol)羰基二咪唑，20mL四氢呋喃加入到100mL三口烧瓶中，加热回流3小时，过滤，依次用二氯甲烷、水洗涤，无水硫酸镁干燥，旋蒸，得白色透明粘稠物，加入到50mL三口烧瓶中，再加入1.85g(12mmol)香叶醇、20mL N，N-二甲基甲酰胺，90℃搅拌6小时。到入到含50mL二氯甲烷和50mL水分液漏斗中，分液，有机相一次用水、饱和氯化钠溶液洗涤，旋蒸，柱层析分离纯化，得淡黄色透明液体2.42g，产率73％。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(300MHz，CDCl3)δ：4.67(dd，J＝18.4，6.5Hz，4H)，4.50(s，2H)，2.09(dd，J＝12.3，6.2Hz，9H)，1.74-1.63(m，12H)，1.59(s，5H).
13C NMR(75MHz，CDCl3)δ：155.28，149.45，143.02，132.14，131.80，126.52，123.64，117.73，108.75，71.79，64.57，59.34，40.67，39.46，30.38，27.19，26.19，25.62，20.70，17.62，16.47.
实施例2.香气评价
取0.01g紫苏醇香叶醇碳酸酯样品配制为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。
紫苏醇香叶醇碳酸酯样品具有青草香、清甜香、酸甜香、柠檬清香。

Claims (1)

1.一种芳香化合物紫苏醇香叶醇碳酸酯，具体化学结构式如下所示：
Figure FSA0000177717790000011
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Publication number Priority date Publication date Assignee Title
CN112480051A (zh) * 2020-12-10 2021-03-12 河南中烟工业有限责任公司 2,3-二氢-3-羟基-6-甲基-4h-吡喃-4-酮-5-o-碳酸香叶醇酯及应用
CN113461535A (zh) * 2021-08-05 2021-10-01 四川三联新材料有限公司 一种香叶醇降龙涎碳酸酯潜香物及其制备方法和应用
CN114380693B (zh) * 2022-03-10 2023-11-17 安徽中烟工业有限责任公司 一种甲基环戊烯醇酮香叶醇碳酸酯香料及其合成方法与应用

Citations (2)

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Publication number Priority date Publication date Assignee Title
US4306099A (en) * 1979-06-19 1981-12-15 Synarome H, Fraysse Et Cie Method of preparation of perillic alcohol and derivatives thereof
CN105296157A (zh) * 2015-12-03 2016-02-03 北京工商大学 一种降龙涎紫苏酯香料

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4306099A (en) * 1979-06-19 1981-12-15 Synarome H, Fraysse Et Cie Method of preparation of perillic alcohol and derivatives thereof
CN105296157A (zh) * 2015-12-03 2016-02-03 北京工商大学 一种降龙涎紫苏酯香料

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Palladium-catalyzed alkoxycarbonylation of allylic natural terpenic functionalized olefins;Soufiane El Houssame,et al.;《Journal of Molecular Catalysis A: Chemical》;20010301;第168卷(第1-2期);第15-23页 *
食品香料香精发展趋势;田红玉 等;《食品科学技术学报》;20180331;第36卷(第2期);第1-11页 *

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