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New compounds identified in agarwood ( Aquilaria agallocha Roxb.)
Author(s) -
Nät Regula,
Velluz Alain,
Thommen Walter,
Brauchli Robert,
Sigwart Christine,
Gaudin JeanMarc
Publication year - 1993
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.2730080604
Subject(s) - agarwood , chemistry , cyclohexanone , diastereomer , dodecane , absolute configuration , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Four new compounds have been isolated from agarwood oil ( Aquilaria agallocha Roxb.) and their structures confirmed by synthesis: ( 1R,2R,6S,9R )‐6,10,10‐trimethyl‐ll‐oxatricyclo[7.2.1.0 1,6 ]dodecane‐2‐spiro‐2′‐oxirane (1) (epoxy‐β‐agarofuran), ( 1S,2S,6S,9R )‐6,10,10‐trimethyl‐11‐oxatricyclo[7.2.1.0 1,6 ]dodecane‐2‐carbaldehyde ( 2 ), (E)‐8,10‐undecadien‐2‐one ( 3 ) and 2,t‐3‐dimethyl‐r‐2‐(3‐methyl‐2‐butenyl)‐l‐cyclohexanone ( 4 , absolute configuration unknown). Several of their diastereoisomers, such as ( 1R,2S,6S,9R )‐6,10,10‐trimethyl‐11‐oxatricyclo [7.2.1.0 1,6 ]dodecane‐2‐spiro‐2′‐oxirane ( 5 ), ( 1S,2R,6S,9R )‐6,10,10‐trimethyl‐11‐oxatricyclo[7.2.1.0 1,6 ] dodecane‐2‐carbaldehyde ( 6 ), (Z)‐8,10‐undecadien‐2‐one ( 7 ) and racemic 2,c‐3‐dimethyl‐r‐2‐(3‐methyl‐2‐butenyl)‐1‐cyclohexanone ( 8 , racemate) were also synthesized and fully characterized. The 13 C NMR data of agarospirol ( 9 ), published earlier, 1 are corrected. The assignments are supported by 1D‐INADEQUATE experiments.