Synthesis and odour evaluation of double‐bond isomers of DAMASCENOLIDE, 4‐(4‐methylpent‐3‐en‐1‐yl)‐2(5H)‐furanone, which has a citrus‐like odour

Miyazawa Yamato; Ohashi Teruhisa; Kawaguchi Kenji; Tanaka Naoko; Katsuta Ryo; Yajima Arata; Nukada Tomoo; Ishigami Ken

摘要

Abstract > Our group recently isolated 4‐(4‐methylpent‐3‐en‐1‐yl)‐2(5 H )‐furanone (DAMASCENOLIDE or MPF), which has a citrus‐like odour, from damask rose ( Rosa damascena ). DAMASCENOLIDE has two double bonds, and we were interested in how the position and the geometric isomerism of these double bonds change the odour. Therefore, we synthesized eleven novel double‐bond isomers of DAMASCENOLIDE and evaluated their odours. Some of them have similar odours to DAMASCENOLIDE, while many others have different odours such as metallic, tropical and fishy. Especially, a Z ‐form double‐bond moiety changed the odour significantly. Regarding the odour intensity, compounds with 2(3 H )‐furanone skeleton tend to be stronger than compounds with 2(5 H )‐furanone skeleton. From these results, it was found that the position and the geometric isomerism of the double bond greatly affected the odour. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：ID =“FFJ3568-ABS-ABS-0001”XML：LANG =“EN”> <标题类型=“main”>抽象</ title> > 我们最近分离4-（4-甲基戊3-ZEN-1-YL）-2（5 h </ i> ） - 从锦缎玫瑰（ rosa damascena </ i> ）。阵塔......有两个双键，我们对这些双键的位置和几何异构体的兴趣改变了气味。因此，我们合成了达摩糖苷的11个新型双键异构体，并评估了它们的气味。其中一些物味与阵大地有类似的气味，而许多其他物味具有不同的气味，如金属，热带和腥味。特别是A. z </ i> - Formform双键部分显着改变了气味。关于气味强度，具有2的化合物（3 h </ i> ） - 呋喃酮骨骼往往比2（5 h </ i> ） - 呋喃酮骨骼。从这些结果来看，发现双键的位置和几何异构性极大地影响了气味。 </ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" > 著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-24420/'>《Flavour and Fragrance Journal 》</a> <b style="margin: 0 2px;">|</b><span>2020年第3期</span><b style="margin: 0 2px;">|</b> <span>共9页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Miyazawa Yamato&option=202" target="_blank" rel="nofollow">Miyazawa Yamato;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ohashi Teruhisa&option=202" target="_blank" rel="nofollow">Ohashi Teruhisa;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kawaguchi Kenji&option=202" target="_blank" rel="nofollow">Kawaguchi Kenji;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Tanaka Naoko&option=202" target="_blank" rel="nofollow">Tanaka Naoko;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Katsuta Ryo&option=202" target="_blank" rel="nofollow">Katsuta Ryo;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yajima Arata&option=202" target="_blank" rel="nofollow">Yajima Arata;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Nukada Tomoo&option=202" target="_blank" rel="nofollow">Nukada Tomoo;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ishigami Ken&option=202" target="_blank" rel="nofollow">Ishigami Ken;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>R&</p> <p>D CenterT. Hasegawa Co. LtdKanagawa Japan;</p> <p>R&</p> <p>D CenterT. Hasegawa Co. LtdKanagawa Japan;</p> <p>R&</p> <p>D CenterT. Hasegawa Co. LtdKanagawa Japan;</p> <p>R&</p> <p>D CenterT. Hasegawa Co. LtdKanagawa Japan;</p> <p>Department of Chemistry for Life Sciences and AgricultureTokyo University of AgricultureSetagaya Tokyo Japan;</p> <p>Department of Chemistry for Life Sciences and AgricultureTokyo University of AgricultureSetagaya Tokyo Japan;</p> <p>Department of Chemistry for Life Sciences and AgricultureTokyo University of AgricultureSetagaya Tokyo Japan;</p> <p>Department of Chemistry for Life Sciences and AgricultureTokyo University of AgricultureSetagaya Tokyo Japan;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li> <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span> <a href="https://www.zhangqiaokeyan.com/clc/1845.html" title="香料及化妆品工业">香料及化妆品工业 ;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=deconjugation&option=203" rel="nofollow">deconjugation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=double‐bond isomer&option=203" rel="nofollow">double‐bond isomer;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=odour evaluation&option=203" rel="nofollow">odour evaluation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=structure‐odour relationships&option=203" rel="nofollow">structure‐odour relationships;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=synthesis&option=203" rel="nofollow">synthesis;</a> </p> <div class="translation"> 机译：Deconjugation;双键异构体;气味评估;结构 - 气味关系;合成; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704023560688.html">Synthesis and odour evaluation of double‐bond isomers of DAMASCENOLIDE, 4‐(4‐methylpent‐3‐en‐1‐yl)‐2(5H)‐furanone, which has a citrus‐like odour</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Miyazawa Yamato&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Miyazawa Yamato,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ohashi Teruhisa&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Ohashi Teruhisa,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kawaguchi Kenji&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Kawaguchi Kenji,</a> <a href="/journal-foreign-24420/" target="_blank" rel="nofollow" class="tuijian_authcolor">Flavour and Fragrance Journal .</a> <span>2020</span> <span>,第3期</span> </span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：阵塔二键二烯醇酯的双键异构体的合成和气味评价，4-（4-甲基戊-3-烯-1-基-1-基）-2（5H） - 呋喃（呋喃酮，其含有柑橘样气味</span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/070406342175.html">Synthesis and odour evaluation of stereoisomers of N-Alkyl-pyrrolidine derivatives, characteristic roast odour of seafood</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Toru Tachihara&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Toru Tachihara,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sysumu Ishizaki&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Sysumu Ishizaki,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yoshiko Kurobayashi&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Yoshiko Kurobayashi,</a> <a href="/journal-foreign-24420/" target="_blank" rel="nofollow" class="tuijian_authcolor">Flavour and Fragrance Journal .</a> <span>2003</span> <span>,第4期</span> </span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：N-烷基-吡咯烷衍生物的立体异构体的合成及气味评价，海鲜的典型烘烤气味</span> </p> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704019019193.html">Synthesis and preliminary odour evaluation of 5alpha-androst-16-en-7-one: a new androstenone analogue</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=John A. 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href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=叶姣&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 叶姣</a> <span> . 2015</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120107292655.html">1-(5′-(5-(3,5-二氯-4-氟苯基)-5-(三氟甲基)-4,5-二氢异噁唑-3-基)-3′H-螺氮杂环丁烷-3,1′-异苯并呋喃-1-基)-2-(甲基磺酰基)乙酮的晶型</a> <b>[P]</b> . <span> 中国专利： CN104812758A </span> <span> . 2015-07-29</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120462219.html">合成2－羟基－N,N－二甲基－3－[[2－[[1(R)－(5－甲基－2－呋喃基)丙基]氨基]－3,4－二氧代－1－环丁烯－1－基]氨基]苯甲酰胺</a> <b>[P]</b> . <span> 中国专利： CN100448860C </span> <span> . 2009.01.07</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130453692466.html">CEPHALOSPORIN COMPOUNDS, THEIR PHARMACEUTICALLY ACCEPTABLE NONTOXIC SALTS, PHYSIOLOGICALLY HYDROLYZABLE ESTERS, ISOMERS HAVING E-CONFIGURATION OF DOUBLE BOND IN PROPENYL GROUP, SYN-ISOMERS AND OPTICAL ISOMERS AND A METHOD OF THEIR SYNTHESIS</a> <b>[P]</b> . <span> 外国专利：  RU2098420C1 </span> <span> . 1997-12-10</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：头孢氨苄化合物，其药学上可接受的非氧化盐，可生理水解的酯，具有戊基双键电子构型的异构体，同分异构体和光学异构体及其合成方法 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704023560688','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" 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