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

doi:10.1016/j.tetasy.2007.02.007

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 journal › Article › peer-review

9 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 language	English
Pages (from-to)	537-541
Number of pages	5
Journal	Tetrahedron Asymmetry
Volume	18
Issue number	4
DOIs	https://doi.org/10.1016/j.tetasy.2007.02.007
Publication status	Published - Mar 12 2007
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1016/j.tetasy.2007.02.007

Cite this

@article{7aa8c1fc2f134779ad9fe32794c1355b,

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

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.",

author = "Hiroki Asao and Hiroyuki Sakauchi and Shigefumi Kuwahara and Hiromasa Kiyota",

year = "2007",

month = mar,

day = "12",

doi = "10.1016/j.tetasy.2007.02.007",

language = "English",

volume = "18",

pages = "537--541",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Limited",

number = "4",

}

TY - JOUR

T1 - Synthesis and odor description of optically active cyclopropanated analogues of geraniol, nerol, nor-leaf alcohol, and matsutake alcohol

AU - Asao, Hiroki

AU - Sakauchi, Hiroyuki

AU - Kuwahara, Shigefumi

AU - Kiyota, Hiromasa

PY - 2007/3/12

Y1 - 2007/3/12

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=33947192371&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33947192371&partnerID=8YFLogxK

U2 - 10.1016/j.tetasy.2007.02.007

DO - 10.1016/j.tetasy.2007.02.007

M3 - Article

AN - SCOPUS:33947192371

SN - 0957-4166

VL - 18

SP - 537

EP - 541

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 4

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this