Enantioselectivity in odor perception:: Synthesis and olfactory properties of iso-β-bisabolol, a new natural product

被引:18
|
作者
Braun, NA [1 ]
Meier, M [1 ]
Schmaus, G [1 ]
Hölscher, B [1 ]
Pickenhagen, W [1 ]
机构
[1] Symrise GmbH & Co KG, Res & Dev, D-37603 Holzminden, Germany
关键词
D O I
10.1002/hlca.200390219
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The odorous trace constituent iso-beta-bisabolol (4) was isolated from East Indian and Western Australian sandalwood oil and synthesized by using the (E/Z)-triene 12 (iso-gamma-bisabolene) as a key intermediate. Only one of four stereoisomeric forms of 4, (6R,7R)-4a, is odor active, having a strong floral, muguet-like, very pleasant scent.
引用
收藏
页码:2698 / 2708
页数:11
相关论文
共 50 条
  • [1] Enantioselectivity in odor perception synthesis and olfactory properties of the new tricyclic sandalwood odorant Fleursandol®
    Hölscher, B
    Braun, NA
    Weber, B
    Kappey, CH
    Meier, M
    Pickenhagen, W
    [J]. HELVETICA CHIMICA ACTA, 2004, 87 (07) : 1666 - 1680
  • [2] Ring-closing olefin metathesis reactions;: synthesis of iso-β-bisabolol
    Mörgenthaler, JM
    Spitzner, D
    [J]. TETRAHEDRON LETTERS, 2004, 45 (06) : 1171 - 1172
  • [3] Total Synthesis of Iso- and Bongkrekic Acids: Natural Antibiotics Displaying Potent Antiapoptotic Properties
    Francais, Antoine
    Leyva-Perez, Antonio
    Etxebarria-Jardi, Gorka
    Pena, Javier
    Ley, Steven V.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (01) : 329 - 343
  • [4] iso-α-Cyclopiazonic acid, a new natural product isolated from the marine-derived fungus Aspergillus flavus C-F-3
    Lin, Ai-Qun
    Du, Lin
    Fang, Yu-Chun
    Wang, Fa-Zuo
    Zhu, Tian-Jiao
    Gu, Qian-Qun
    Zhu, Wei-Ming
    [J]. CHEMISTRY OF NATURAL COMPOUNDS, 2009, 45 (05) : 677 - 680
  • [5] iso-α-Cyclopiazonic acid, a new natural product isolated from the marine-derived fungus Aspergillus flavus C-F-3
    Ai-Qun Lin
    Lin Du
    Yu-Chun Fang
    Fa-Zuo Wang
    Tian-Jiao Zhu
    Qian-Qun Gu
    Wei-Ming Zhu
    [J]. Chemistry of Natural Compounds, 2009, 45 : 677 - 680
  • [6] SYNTHESIS AND OLFACTORY PROPERTIES OF SOME THIAZOLES WITH BELL PEPPER LIKE ODOR
    PELOSI, P
    PASQUALETTO, P
    LORENZI, R
    [J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1983, 31 (03) : 482 - 484
  • [7] Enantioselective microbial synthesis of the indigenous natural product (-)-α-bisabolol by a sesquiterpene synthase from chamomile (Matricaria recutita)
    Son, Young-Jin
    Kwon, Moonhyuk
    Ro, Dae-Kyun
    Kim, Soo-Un
    [J]. BIOCHEMICAL JOURNAL, 2014, 463 : 239 - 248
  • [8] New directions in natural product synthesis
    Davies, Huw M. L.
    Itami, Kenichiro
    Stoltz, Brian M.
    [J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (21) : 7828 - 7829
  • [9] NEW APPROACH TO THE SYNTHESIS OF THE NATURAL PRODUCT ARIPUANIN
    Lazaro, Aline S.
    Zana Ribeiro, Pedro H.
    Sairre, Mirela I.
    Donate, Paulo M.
    [J]. SYNTHETIC COMMUNICATIONS, 2015, 45 (11) : 1374 - 1378
  • [10] A New Synthesis of Stilbene Natural Product Piceatannol
    Han, Su Young
    Bang, Hyun Bae
    Lee, Hyun Suck
    Hwang, Jung Woon
    Choi, Da Hye
    Yang, Deok Mo
    Jun, Jong-Gab
    [J]. BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (09): : 1800 - 1802