New separation method for terpenoids in byproducts discharged during sugi wood-drying process, and purification of ferruginol

Journal of Wood Science

Official Journal of the Japan Wood Research Society

Table 1 Chemical composition of steam distillates (SD), solvent extracts (SE) and samples of byproducts discharged after wood-drying processes (BWP)

No.	Compound	RRT^a	KI^b	Relative peak area (%)
No.	Compound	RRT^a	KI^b	SD	SE	BWP
1	Muurola-3,5-diene<trans->	0.73	1453	1.54	–^c	–
2	Amorpha-4,7(11)-diene	0.76	1481	3.00	–	–
3	Muurola-4(14),5-diene<trans->	0.78	1493	3.92	0.38	–
4	epi-Cubebol	0.78	1494	3.49	6.23	3.31
5	α-Muurolene	0.78	1500	3.92	1.85	0.71
6	Cubebol	0.80	1515	4.29	17.07	4.18
7	δ-Cadinene	0.81	1523	20.79	2.29	3.58
8	Cadina-1,4-diene<trans->	0.82	1534	1.57	–	–
9	Elemol	0.84	1549	4.65	1.75	1.16
10	Gleenol	0.88	1587	1.26	–	–
11	1-epi-Cubenol	0.92	1628	9.93	1.14	2.70
12	γ-Eudesmol	0.93	1632	2.20	0.51	–
13	Cubenol	0.94	1646	5.87	–	2.18
14	α-Muurolol	0.94	1646	2.17	0.40	1.01
15	β-Eudesmol	0.95	1650	5.30	1.53	1.68
16	α-Eudesmol	0.95	1653	5.44	0.87	1.26
16	n-Heptadecane (internal standard)	1.00	1700
17	Cryptomerione	1.02	1724	3.59	1.64	1.23
18	Cryptomeridiol	1.11	1813	–	0.61	–
19	Bisabolatrien-1-ol-4-one<2,7(14),10->	1.14	1845	1.23	2.67	1.51
20	11-Acetoxyeudesman-4α-ol	1.23	1939	–	1.39	1.26
21	Sandaracopimara-8(14),15-diene	1.26	1969	–	0.46	1.11
22	Manool	1.34	2057	–	–	2.04
23	Abietadiene	1.36	2087	0.69	1.69	6.39
24	Sandaracopimarinal	1.44	2184	1.34	3.62	6.08
25	Phyllocladanol	1.47	2210	–	–	5.59
26	Sandaracopimarinol	1.51	2269	3.58	13.89	18.74
27	6,7-dehydroferruginol	1.55	2315	–	10.13	7.97
28	Ferruginol	1.56	2332	2.18	14.24	16.45
29	3-α-acetoxy-Manool	1.58	2360	–	1.02	1.23
Sesquiterpene hydrocarbons				34.74	4.52	4.29
Oxygenated sesquiterpenes				49.42	35.81	21.48
Diterpene hydrocarbons				0.69	2.15	7.50
Oxygenated diterpenes				7.10	42.90	58.10
Total identified components				91.95	85.38	91.37

^aRelative retention time (RRT) was calculated based on the retention time of n-heptadecane (internal standard)
^bKovats index was cited from the reference data [14]
^cNot detected