7.2.1 Historical Overview of the Isolation and Structure
Elucidation of (-)-D^9 -Trans-Tetrahydrocannabinol
(D^9 -THC) Type CannabinoidsSeveral investigations have been carried out over the years to isolateD^9 - THC from
Cannabisplant material, due to the large and important applications of THC in the
pharmacological activities. Many column chromatography and countercurrent dis-
tribution methods using various adsorbents as silica gel, silicic acid, silicic
acid-silver nitrate,florisil, acid washed alumina, and acid washed alumina-silver
nitrate were used for the preparative isolation of D^9 -THC.
OOH2 (Δ^9 -THCA-C 5 A)OOH
C9
O
OOOH OHO1011 121314(^1615)
17
18 (cannabisol)
O
8 OH
19
20
O
OH
C
O
2
2 H
22 (Δ^9 -THC-aldehyde )
O
OH
21
O O
O
O
8 OH
23 (8-oxo-Δ^9 -THC)
O
COOH
O
OH
3 (Δ^9 -THCA-C 5 B)
COOH
O
OH
5 (Δ^9 -THCA-C 4 A)
COOH
O
OH
4 (Δ^9 -THC-C 4 )
O
OH
7 (Δ^9 -THCVA-C 3 A)
COOH
O
OH
1 (Δ^9 -THC-C 5 )
O
OH
6 (Δ^9 -THCV-C 3 )
O
OH
8 (Δ^9 -THCO-C 1 )
O
OH
9 (Δ^9 -THCOA-C 1 A)
COOH
11
O
8 OH
HO
HO
Fig. 7.1 (-)-Δ^9 - trans-tetrahydrocannabinol (Δ^9 -THC)-type cannabinoids ( 1 – 23 )
7 Natural Cannabinoids of Cannabis and Methods of Analysis 167