Title: Patchouli Alcohol
CAS Registry Number: 5986-55-0
CAS Name: [1R-(1a,4b,4aa,6b,8aa)]-Octahydro-4,8a,9,9-tetramethyl-1,6-methanonaphthalen-1(2H)-ol
Additional Names: patchouli camphor
Molecular Formula: C15H26O
Molecular Weight: 222.37
Percent Composition: C 81.02%, H 11.79%, O 7.19%
Literature References: A tricyclic sesquiterpene alcohol isolated from oil of patchouli: Gadamer, Amenomiya, Arch. Pharm. 241, 39 (1903). Proposed structure: Treibs, Ann. 564, 141 (1949). Revised structure: Dobler et al., Proc. Chem. Soc. London 1963, 383. Structural studies: Büchi et al., J. Am. Chem. Soc. 78, 1262 (1956); 83, 927 (1961); 84, 3205 (1962); 86, 4438 (1964). Synthesis of dl-form: Danishevsky, Dumas, Chem. Commun. 1968, 1287; Mirrington, Schmalzl, J. Org. Chem. 37, 2871 (1972); K. Yamada et al., Tetrahedron 35, 293 (1979). Stereoselective total synthesis of racemic form: F. Näf, G. Ohloff, Helv. Chim. Acta 57, 1868 (1974); of natural, racemic and (+)-forms: F. Näf et al., ibid. 64, 1387 (1981). Review: Walker, Manuf. Chem. Aerosol News 39, no. 7, 27 (1968).
Properties: Large crystals (hexagonal-trapezohedral) from the higher boiling fractions of oil of patchouli or from petr ether, mp 56°. mp (racemate) 39-40° (Danishevsky, Dumas); also reported as mp 46-47° (Mirrington, Schmalzl). bp8 140°. d420 1.0284. [a]D20 -97.4° (c = 24 in chloroform). nD65 1.5029. Practically insol in water. Sol in alcohol, ether, common organic solvents.
Melting point: mp 56°; mp (racemate) 39-40° (Danishevsky, Dumas); mp 46-47° (Mirrington, Schmalzl)
Boiling point: bp8 140°
Optical Rotation: [a]D20 -97.4° (c = 24 in chloroform)
Index of refraction: nD65 1.5029
Density: d420 1.0284 |