4556. Guaiol
Nomenclature
CAS number: 489-86-1
[3S-(3α,5α,8α)]-1,2,3,4,5,6,7,8-Octahydro-α,α,3,8-tetramethyl-5-azulenemethanol; 3,8-dimethyl-5-(α-hydroxyisopropyl)-Δ9-octahydroazulene; champaca camphor; champacol; guaiac alcohol; Guajol. C15H26O; mol wt 222.37.
C 81.02%, H 11.79%, O 7.19%.
Description and references
A sesquiterpene alc from guaiac wood: Michelia champaca L., Magnoliaceae: also from oil of wood of Bulnesia sarmienti Lorentz, Zygophyllaceae. Isoln: Plattner, Lemay, Helv. Chim. Acta 23, 897 (1940). Structure: Plattner, Magyar, ibid. 25, 581 (1942). Stereochemistry: Takeda, Minato, Tetrahedron Lett. 1960 (22), 33; Minato, Chem. Pharm. Bull. 9, 625 (1961); idem, Tetrahedron 18, 365 (1962). Total synthesis of dl-form: Buchanan, Young, Chem. Commun. 1971, 643; eidem, J. Chem. Soc. Perkin Trans. 1 1973, 2404; Marshall et al., Tetrahedron Lett. 1971, 885; Marshall, Greene, J. Org. Chem. 37, 982 (1972); Andersen, Uh, Tetrahedron Lett. 1973, 2079.
Properties
Trigonal pyramidal crystals from alc, mp 91°. d20100 0.9074. bp760 288° (slight decompn); bp17 165°; bp10 148°. [α]D20 30° (c = 4 in alc). nD100 1.4716. Sol in alc, ether. Insol in water.Derivative
Methyl ether.C16H28O; mol wt 236.39.
C 81.29%, H 11.94%, O 6.77%.