Title: Guaiol
CAS Registry Number: 489-86-1
CAS Name: [3S-(3a,5a,8a)]-1,2,3,4,5,6,7,8-Octahydro-a,a,3,8-tetramethyl-5-azulenemethanol
Additional Names: 3,8-dimethyl-5-(a-hydroxyisopropyl)-D9-octahydroazulene; champaca camphor; champacol; guaiac alcohol
Trademarks: Guajol
Molecular Formula: C15H26O
Molecular Weight: 222.37
Percent Composition: C 81.02%, H 11.79%, O 7.19%
Literature 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°. [a]D20 -30° (c = 4 in alc). nD100 1.4716. Sol in alc, ether. Insol in water.
Melting point: mp 91°
Boiling point: bp760 288° (slight decompn); bp17 165°; bp10 148°
Optical Rotation: [a]D20 -30° (c = 4 in alc)
Index of refraction: nD100 1.4716
Density: d20100 0.9074
Derivative Type: Methyl ether
Molecular Formula: C16H28O
Molecular Weight: 236.39
Percent Composition: C 81.29%, H 11.94%, O 6.77%
Properties: Liq, d425 0.9332. bp9 142°. [a]D20 -31.8°. nD18.5 1.4896.
Boiling point: bp9 142°
Optical Rotation: [a]D20 -31.8°
Index of refraction: nD18.5 1.4896
Density: d425 0.9332
NOTE: The name "guaiol" is also applied to 1,2-dimethylacrolein, isolated from guaiacum resin. |