CN111517957B - 一种紫苏醇薄荷醇碳酸酯香料 - Google Patents

一种紫苏醇薄荷醇碳酸酯香料 Download PDF

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CN111517957B
CN111517957B CN201910038742.6A CN201910038742A CN111517957B CN 111517957 B CN111517957 B CN 111517957B CN 201910038742 A CN201910038742 A CN 201910038742A CN 111517957 B CN111517957 B CN 111517957B
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carbonate
menthol
spice
perilla alcohol
fragrance
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CN111517957A (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
    • C07C2601/14—The ring being saturated
    • 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)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)

Abstract

本发明公开了一种化合物紫苏醇薄荷醇碳酸酯，具体化学结构式如下所示：

Description

一种紫苏醇薄荷醇碳酸酯香料
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薄荷醇碳酸酯，它通过以下通式表示：
Figure BSA0000177717570000011
具体实施方式
实施例1.紫苏醇薄荷醇碳酸酯的制备
合成路线如下式所示：
Figure BSA0000177717570000012
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1.87g(12mmol)薄荷醇、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1.94g，产率58％。
产物经过核磁氢谱及核磁碳谱表征。
1H NMR(300MHz，CDCl3)δ：5.78(s，1H)，4.70(d，J＝5.4Hz，2H)，4.50(t，J＝4.7Hz，3H)，2.16-2.06(m，4H)，1.96(d，J＝2.6Hz，2H)，1.72(s，3H)，1.66(d，J＝10.6Hz，2H)，1.52-1.34(m，3H)，1.04(d，J＝11.4Hz，2H)，0.94-0.84(m，8H)，0.79(t，J＝6.7Hz，4H).
13C NMR(75MHz，CDCl3)δ：154.95，149.45，132.23，126.34，108.75，78.20，71.57，46.95，40.72，34.08，31.36，30.39，27.20，26.10，23.27，21.94，20.69，16.20.
实施例2.香气评价
取0.01g紫苏醇薄荷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。
紫苏醇薄荷醇碳酸酯样品具有略带刺激的清凉香、柑橘香。

Claims (1)

1.一种芳香化合物紫苏醇薄荷醇碳酸酯，具体化学结构式如下所示：
Figure FSA0000177717560000011
CN201910038742.6A 2019-01-16 2019-01-16 一种紫苏醇薄荷醇碳酸酯香料 Active CN111517957B (zh)

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CN113979864A (zh) * 2021-11-12 2022-01-28 云南中烟工业有限责任公司 一种新型薄荷醇碳酸酯类凉味剂的一锅法合成方法及其在卷烟中的应用

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