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Constituents of commercial Labdanum oil

โœ Scribed by Peter Weyerstahl; Helga Marschall; Marlies Weirauch; Katrin Thefeld; Horst Surburg


Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
402 KB
Volume
13
Category
Article
ISSN
0882-5734

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โœฆ Synopsis


Commercial Labdanum oil contains more than 300 constituents. 186 compounds (154 from the neutral part, 32 from the acidic part), representing about 95% of the oil, were identiยฎed mainly by their NMR spectra. Typical for the Labdanum oil in the C 15 to C 20 region are aromadendrane (23%), cadinane (9%) and labdane (7%) derivatives, mostly oxidized. The main constituents in this region are ledene (92, 9.3%), alloaromadendrene (86, 1.5%), 1,5-cis-aromadendr-9-ene (91, 1.4%), viridiยฏorol (112, 4.3%), 1,2-dehydroviridi-ยฏorol (104, 1.4%), ledol (116, 1.3%), palustrol (105, 1.2%), the new cubeban-11-ol (113, 4.1%), copaborneol (117, 1.8%), and ambrox 1 (137, 1.4%). The following new natural compounds were isolated: 1. C 9 3 C 14 compounds: 2,2,5-trimethyloxepan-4-one (30), cis-p-menth-4(8)-en-2-ol (40), (2E,4E)-6-hydroxy-2,6-dimethylhepta-2,4-dienal (59), cis-5-hydroxymentha-1(6),8-dien-2-one (71), 7-acetyl-2,2,6-trimethylbicyclo[4.2.0]octane (72), 4,4,7a-trimethyl-1,4,5,6,7,7a-hexahydro-2H-inden-2-one (83), 6-acetyl-5,8,8-trimethylbicyclo[3.2.1]octan-2,3-dione (119), 1,1,5,6-tetramethyl-1,2-dihydro-( ) and 1,1,5,6-tetramethyl-1,2,3,4-tetrahydronaphthalene (95). 2. Sesquiterpenes: cubeb-11-ene ( ), 1,2-dehydroglobulol ( ), 1-epi-3,4-dehydroviridiยฏorol (110), 3,4dehydroglobulol (118), muurola-4,10( )-dien-1-ol (120), 5-epi-( ) and 1,10-seco-aromadendran-1,10-dione (132), 5,11-epoxycadin-1(10)-en-9-ol (136), 10-hydroxycalamenene-8,9-epoxide (140) as well as 9(10 3 1)-abeo-9-hydroxy-aromadendran-10-one (131) named by us as 9-hydroxy-ladanifer-10-one, possessing a new skeleton. 3. Labdane derivatives: 7-( ), 8-( ) and 8(17)-15-nor-labdene (142). 4. From the acidic part: 3-isobutenyl-5methyl-5-vinylbutyrolactone (M21), dimethyl (Z)-2-n-hexyl-3-methylbutendioate (M24) and the two epimers of methyl 1,5,5-trimethylbicyclo[4.1.0] heptan-7-carboxylate (M16, M,17).


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