Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol

Hiroki Asao, Hiroyuki Sakauchi, Shigefumi Kuwahara, Hiromasa Kiyota

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Both enantiomers of cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol were synthesized and their odor properties evaluated. Odor characters in enantiomeric pairs were similar in the geraniol series. The (+)-(2R,3S)-nerol derivative showed various odor aspects. From the results of nor-leaf alcohol derivatives, an interaction between the (2-re,3-re)-face of nor-leaf alcohol and the human olfactory receptor was suggested. The odor of (3R)-matsutake alcohol derivative was superior to the enantiomer.

Original languageEnglish
Pages (from-to)537-541
Number of pages5
JournalTetrahedron Asymmetry
Volume18
Issue number4
DOIs
Publication statusPublished - Mar 12 2007
Externally publishedYes

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odors
Odors
leaves
alcohols
Alcohols
analogs
synthesis
Enantiomers
enantiomers
Derivatives
Odorant Receptors
geraniol
Odorants
interactions

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol. / Asao, Hiroki; Sakauchi, Hiroyuki; Kuwahara, Shigefumi; Kiyota, Hiromasa.

In: Tetrahedron Asymmetry, Vol. 18, No. 4, 12.03.2007, p. 537-541.

Research output: Contribution to journalArticle

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