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Agarwood oil ( Aquilaria agallocha Roxb.). Its composition and eight new valencane‐, eremophilane‐ and vetispirane‐ derivatives
Author(s) -
Näf R.,
Velluz A.,
Brauchli R.,
Thommen W.
Publication year - 1995
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.2730100306
Subject(s) - agarwood , chemistry , carbon skeleton , stereochemistry , medicine , alternative medicine , pathology
The profile of the total extract of agarwood oil ( Aquilaria agallocha Roxb.) is discussed and eight new sesquiter‐penoids are presented: two with the eremophilane‐skeleton ( rel‐(2R,8S,8aR )‐2‐(1,2,3,5,6,7,8,8a‐octahydro‐8,8a‐dimethy1‐2‐naphthyl)‐prop‐2‐en‐1‐ol ( 1 , eremophila‐9,11(13)‐dien‐12‐ol) and rel ‐( 3R,7R,9R,10S )‐9,10‐dimethyl‐6‐methylene‐4‐oxatricyclo[7.4.0.0 3,7 ]tridec‐1‐ene ( 2 , 8,12‐epoxy‐eremophila‐9,11(13)‐diene)), one with the valencane‐skeleton ( rel ‐( 2R,8S,8aR )‐2‐(1,2,6,7,8,8a‐hexahyro‐8,8a‐dimethyl‐2‐naphthyl)‐propan‐2‐ol ( 3 , valenca‐1(10),8‐dien‐11‐ol)) and four with the vetispirane‐skeleton ( rel‐(5R,10R) ‐(2‐isopropylidene‐10‐methyl‐spiro[4,5]dec‐6‐ene‐6‐carbaldehyde ( 4 , vetispira‐2(11),6‐dien‐14‐al), rel‐(5R,7R,10R) ‐2‐isopropylidene‐10‐methyl‐6‐rnethylene‐spiro[4.5]decan‐7‐01 ( 5 , vetispira‐2(11),6(14)‐dien‐7‐01), rel‐(1R,2R) ‐9‐isopropyl‐2‐rnethyl‐8‐oxatricyclo[7.2.1.0 1,6 ]dodec‐5‐ene ( 6 , 2,14‐epoxy‐vetispir‐6‐ene) and rel‐(1R,2R) ‐(9‐isopropyl‐2‐methyl‐8‐oxatricyclo[7.2.1.0 1,6 ]dodeca‐4,6‐diene ( 7 , 2,14‐epoxy‐vetispira‐6(14),7‐diene)). 2‐(1,2,3,5,6,7,8,8a‐octahydro‐8,8a‐dimethyl‐2‐naphthyl)‐propanal ( 8 , valenc‐ or eremophil‐9‐en‐12‐al) is tentatively identified.