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
  • [31] NEW ORGANOLITHIUM REAGENTS AND REACTIONS DISCOVERED IN THE COURSE OF NATURAL PRODUCT SYNTHESIS
    FUNK, RL
    BOLTON, GL
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 193 : 25 - INOR
  • [32] NATURAL PRODUCT CHEMISTRY .140. SYNTHESIS OF SOME NEW ACRIDONES
    REISCH, J
    HERATH, HMTB
    KUMAR, NS
    [J]. LIEBIGS ANNALEN DER CHEMIE, 1990, (10): : 1047 - 1049
  • [33] A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives
    Lei, Kang
    Sun, Dong-Wei
    Tao, Yuan-Yuan
    Xu, Xiao-Hua
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 2016, 69 (01) : 98 - 106
  • [34] New applications of the Ireland Claisen rearrangement in natural product synthesis.
    McIntosh, MC
    Hong, SP
    Lindsay, HA
    Yaramasu, T
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U99 - U99
  • [35] Investigating the anticancer properties of the two new platinum complexes with iso- and tert-pentylglycine by the DFT, molecular docking, and ADMET assessment and experimental confirmations
    Ramezani, Nadali
    Eslami Moghadam, Mahboube
    Behzad, Mahdi
    [J]. JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2021, 26 (2-3): : 283 - 298
  • [36] Investigating the anticancer properties of the two new platinum complexes with iso- and tert-pentylglycine by the DFT, molecular docking, and ADMET assessment and experimental confirmations
    Nadali Ramezani
    Mahboube Eslami Moghadam
    Mahdi Behzad
    [J]. JBIC Journal of Biological Inorganic Chemistry, 2021, 26 : 283 - 298
  • [37] Catalytic Enantioselective Olefin Metathesis in Natural Product Synthesis. Chiral Metal-Based Complexes that Deliver High Enantioselectivity and More
    Hoveyda, Amir H.
    Malcolmson, Steven J.
    Meek, Simon J.
    Zhugralin, Adil R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (01) : 34 - 44
  • [38] SYNTHESIS OF BIOACTIVE COMPOUNDS FROM ABUNDANT NATURAL PRODUCT .13. THE SYNTHESIS AND ANALGESIC PROPERTIES OF NEW SPIROISOCHROMANYL ACID-DERIVATIVES SYNTHESIZED FROM NATURAL SAFROLE
    CABRAL, LM
    BARREIRO, EJ
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (03) : 959 - 962
  • [39] Properties and Mechanisms of Flavin-Dependent Monooxygenases and Their Applications in Natural Product Synthesis
    Deng, Yaming
    Zhou, Quan
    Wu, Yuzhou
    Chen, Xi
    Zhong, Fangrui
    [J]. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2022, 23 (05)
  • [40] New Display Technologies: The Most Desired Usage Properties and Their Perception during Product Interaction
    Agost, Maria-Jesus
    Bayarri-Porcar, Vicente
    [J]. APPLIED SCIENCES-BASEL, 2024, 14 (15):