Cyclopropane ring could be a substitute of C=C double bond in view of stric and electric nature. Synthetic substitute of the double bond of odorants with cyclopropane ring have been prepared and their odor qualty was investigated. As a result, odor characteristic changed and odor intensity increased for some jasmone derivatives. For example, cyclopropanation of the double of the side chain gave good results, however, substitution of the ring double bond lost its original odor.
Odor of jasmones
Odor of jasmonates
65. "Syntheses and odour descriptions of jasmine lactone and cis-jasmone analogues bearing cyclopropane moieties"
H. Kiyota, E. Higashi, T. Koike, T. Oritani, Flavour and Fragrance Journal, 16(3), 175-179 (2001).
51. "Syntheses and Odor Descriptions of Cyclopropanated Compounds 2. Analogues of Methyl Jasmonate"
H. Kiyota, T. Koike, E. Higashi, T. Oritani, Flavour and Fragrance Journal, 17, 267-271 (2002).
40. "Syntheses and Odor Descriptions of Cyclopropanated Compounds 5. Analogues of Methyl Jasmonate to Fix the Relative Stereochemistry of the Two Side Chains."
H. Kiyota, S. Takigawa, S. Kuwahara, Helvetica Chimica Acta, 871854-1859 (2004).
2. Terpenoids and aliphatic alcohols
Cyclopropantion of the double bonds of leaf alcohol derivatives fairly afforded good results. Mono-cyclopropanation of dienols strengthened their odor, however, di-cyclopropanation gave poor results.
Odor of leaf alcohols
Odor of nor-leaf alcohol, matsutake alcohol
Odor of dienols
Odor of tepene alcohols
105. "Synthesis and Odor Description of Optically Active Cyclopropanated Analogs of Geraniol, Nerol, Nor-leaf Alcohol and Matsutake Alcohol. (Syntheses and Odor Descriptions of Cyclopropanated Compounds 7)"
Hiroki Asao, Hiroyuki Sakauchi, Shigefumi Kuwahara, Hiromasa Kiyota, Tetrahedron: Asymmetry, 18 (4), 537-541 (2007).
89. "Syntheses and Odor Descriptions of Cyclopropanated Compounds 3. Analogues of Leaf Alcohol, Its esters and leaf acetal"
H. Kiyota, E. Higashi, T. Koike, T. Oritani, Flavour and Fragrance Journal, 17, 227-231 (2002).
57. "Syntheses and Odor Descriptions of Cyclopropanated Compounds 4. Modification of Aliphatic Dienols"
H. Kiyota, T. Takai, S. Kuwahara, Flavour and Fragrance Journal, 18, 100-105 (2004).
52. "Syntheses and Odor Descriptions of Cyclopropanated Compounds 5. Analogs of Terpene Alcohols and Aliphatic Alcohols"
H. Sakauchi, H. Asao, T. Hasaba, H. Kiyota, S. Kuwahara, Chem. Biodivers., 3, 544-552 (2006).