CN111440071B - 一种紫苏醇肉桂醇碳酸酯香料 - Google Patents

一种紫苏醇肉桂醇碳酸酯香料 Download PDF

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CN111440071B
CN111440071B CN201910038745.XA CN201910038745A CN111440071B CN 111440071 B CN111440071 B CN 111440071B CN 201910038745 A CN201910038745 A CN 201910038745A CN 111440071 B CN111440071 B CN 111440071B
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alcohol
carbonate
spice
perilla
cinnamyl
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CN111440071A (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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Huanan Nongshengyuan Food Co ltd
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
    • 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
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
    • 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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  • Chemical & Material Sciences (AREA)
  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

本发明公开了一种化合物紫苏醇肉桂醇碳酸酯，具体化学结构式如下所示：

Description

一种紫苏醇肉桂醇碳酸酯香料
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。
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l-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；l-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；dl-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肉桂醇碳酸酯，它通过以下通式表示：
Figure BSA0000177717890000011
具体实施方式
实施例1.紫苏醇肉桂醇碳酸酯的制备
合成路线如下式所示：
Figure BSA0000177717890000012
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1.61g(12mmol)肉桂醇、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，得白色透明液体1.53g，产率49％。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(300MHz，CDCl3)δ：δ7.47-7.18(m，5H)，6.70(d，J＝15.9Hz，1H)，6.31(dt，J＝15.9，6.4Hz，1H)，5.83(s，1H)，4.89-4.64(m，4H)，4.55(s，2H)，2.15(dd，J＝12.0，8.3Hz，4H)，1.91(ddd，J＝14.9，9.6，7.6Hz，2H)，1.74(s，3H)，1.63-1.35(m，1H).
13C NMR(75MHz，CDCl3)δ：155.04，149.39，136.02，134.64，132.04，128.54，128.10，126.66，122.49，108.77，71.99，68.23，40.64，30.38，27.17，26.21，20.69.
实施例2.香气评价
取0.01g紫苏醇肉桂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。
紫苏醇肉桂醇碳酸酯样品具有花香、清凉的柑橘香、檀木香。

Claims (1)

1.一种芳香化合物紫苏醇肉桂醇碳酸酯，具体化学结构式如下所示：
Figure FSA0000177717880000011
CN201910038745.XA 2019-01-16 2019-01-16 一种紫苏醇肉桂醇碳酸酯香料 Active CN111440071B (zh)

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CN113461534A (zh) * 2021-08-05 2021-10-01 四川三联新材料有限公司 一种肉桂醇降龙涎碳酸酯潜香物及其制备方法和应用
CN113480432A (zh) * 2021-08-05 2021-10-08 四川三联新材料有限公司 一种紫苏醇降龙涎碳酸酯潜香物及其制备方法和应用
CN114524732A (zh) * 2022-02-24 2022-05-24 石家庄圣泰化工有限公司 甲基羧酸-2-丙炔基酯的合成方法

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

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》;20080331;第36卷(第2期);第1-11页 *

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