Constituents of the Brazilian Cangerana Oil

✍ Scribed by Peter Weyerstahl; Sabina Schneider; Helga Marschall

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 685 KB
• Volume: 11
• Category: Article
• ISSN: 0882-5734
• DOI: 10.1002/(sici)1099-1026(199603)11:2<81::aid-ffj553>3.0.co;2-8

✦ Synopsis

The main components of the commercial Brazilian Cangeruna oil are sesquiterpene hydrocarbons with the caryophyllane, cadinane and germacrane skeleton. The trace constituents epoxycaryophyllanes 9 and 11, 4,lOepoxy-muurolane (18) and -amorphane (19), y-amorphene (22), cyclocaryophyllanol (M), caryolanol (39), guaiadienol ('alismol', 50), amorphen-10-01 (62), and the hydroxycalamenenes (60 and 63) are characterized by their NMR data. KEY WORDS Cangerana oil; Cabralea cangerana Sald. syn. C. gluberrima A. Juss.; Meliaceae; sesquiterpenes; y-amorphene; 4,lO-epoxyamorphane; caryophyllene derivatives JNTRODUCTION Commercial' Cungerunu oil is steam-distilled from the bark of the root of a Brazilian tree.2 This tree, 25-30m high, Cubruleu cungerunu Sald. syn. C. gluberrimu A. Juss. (Meliaceae) only grows in the federal state of Rio Grande do Sul. Its red, pleasant-smelling wood is locally used for housebuilding, parquet and furniture, since it is very resistant to humidity. The bark of the root is also used as antipyretic. The essential oil is employed for soap, floor-waxes, and other perfumed household articles in the local market.2 It has a mildwoody, fatty-greasy, fresh-spicy odour.2 In 1985 Mot1 analysed this oil. He identified some of the main constituents (6-(2) and f3-elemene (7), acopaene (6), (-)-pcaryophyllene (lo), ymuurolene (17), 6-cadinene (29), a-calacorene (32))

and also some of the trace constituents (safrol (l), a-cubebene (3), 4,8-p-epoxycaryophyllene (ll), junenol (49), and juniper camphor (66)) (see Table 1).

from the 5:l mixture with 9): 6 0.895/1.04, 0.901 1.07 (2 s, 11-Me2), 1.0311.17 (s, 4-Me), 1.12h.25 rated by FC and all compounds identified by P -H-5 ) , 1580 (DB-Wax). 'H-NMR (CDC13/C&6, 5 ) , 1591 (DB-Wax). 'H-NMR (CDCl3/Ca6, CCC 0882-5734/%/020081-14 @ 1996 by John Wiley & Sons, Ltd.