Preparation of Campholenal Analogues: Chirons for the lipophilic moiety of sandalwood‐like odorant alcohols

Abstract

In connection with structure-activity relationship studies, analogues of campholenal ((+)-4b), an important building block for sandalwood-like odorants, were prepared. The five-membered-ring analogues 4 were obtained by epoxidation of the corresponding a -pinene derivatives 2, followed by catalytic ZnBr, isomerisation (Scheme 2). The six-membered-ring skeleton was obtained by ozonolysis of a -campholenyl acetate ((-)-14b), followed by intramolecular aldol condensation (Scheme 5 ) . I3C-NMR assignments are given.

Trace Volatile Components in Essential Oil of Citrus sudachi by Means of Modified Solvent Extraction Method

“…Myrtenal gave a refreshing and herbaceous aroma with a medium-low detection threshold (0.055 ppm); however, since it was only a trace, it was not a potent volatile compound. ␣-Campholenal (sandalwood-like aroma) is reported in various kinds of plants and its structure-odor correlations have been well described (Chapuis & Brauchli, 1992).…”

Analysis ofJuniperus communis subsp.alpina needle, berry, wood and root oils by combination of GC, GC/MS and13C-NMR

“…[21][22][23] A few constituents were identified by comparison of their spectral data (MS and/or 13 C-NMR) with those reported in the literature: (i) MS and 13 C-NMR, pmentha-1,8-dien-4-ol (37), 24 amorpha-4,11-diene (89), 19 γ-eudesmol (129), 25 manool (144) 26 and ferruginol (146); 27 (ii) MS, selina-4(15), 7(11)-diene (112); 19 iii) 13 C-NMR: α-campholenyl acetate (63), 28 longiborneol (121), 29 sesquithuriferol (120) 30 and juniper cedrol (119).…”

Synthesis of Deuterium‐Labeled Perfume Ingredients as Internal Standards for Their GC/MS Quantification

“…The org. phase was washed to neutrality with H 2 O, dried (Na 2 SO 4 ), and concentrated and the residue bulb-to-bulb distilled: (À)-14 (14), 109 (27), 72 (100), 43 (28). 15).…”

“…808/3.01 mbar. IR: 2966IR: , 2929IR: , 2873IR: , 2228IR: , 2161IR: , 2066IR: , 1702IR: , 1455IR: , 1380IR: , 1321IR: , 1247IR: , 1230IR: , 1172IR: , 1162IR: , 1123IR: , 1050IR: , 1031IR: , 1001 IR: 3055, 3014, 2960IR: 3055, 3014, , 2920IR: 3055, 3014, , 2878IR: 3055, 3014, , 2856IR: 3055, 3014, , 2222IR: 3055, 3014, , 2157IR: 3055, 3014, , 2073IR: 3055, 3014, , 1492IR: 3055, 3014, , 1457IR: 3055, 3014, , 1380IR: 3055, 3014, , 1346IR: 3055, 3014, , 1204IR: 3055, 3014, , 1172IR: 3055, 3014, , 1147IR: 3055, 3014, , 1122IR: 3055, 3014, , 1085IR: 3055, 3014, , 1056IR: 3055, 3014, , 1040IR: 3055, 3014, , 1025 (27), 41 (28). 3,6-trimethylcyclohexanecarbaldehyde (7).…”

“…IR: 3360, 2921IR: 3360, , 2861IR: 3360, , 2225IR: 3360, , 2133IR: 3360, , 1686IR: 3360, , 1460IR: 3360, , 1384IR: 3360, , 1363IR: 3360, , 1339IR: 3360, , 1289IR: 3360, , 1248IR: 3360, , 1206IR: 3360, , 1186IR: 3360, , 1134IR: 3360, , 1103IR: 3360, , 1066IR: 3360, , 1047IR: 3360, , 1029 1 H-NMR: 0. (27).…”