5430. Ledol
Nomenclature
CAS number: 577-27-5
[1aR-(1aα,4α,4aβ,7α,7aβ,7bα)]-Decahydro-1,1,4,7-tetramethyl-1H-cycloprop[e]azulen-4-ol; “Ledum camphor”. C15H26O; mol wt 222.37.
C 81.02%, H 11.79%, O 7.19%.
Description and references
Occurs in the essential oil from leaves of Ledum palustre L.: Grassmann, Repert. Pharm. 38, 53 (1931); Hjelt, Ber. 28, 3087 (1895); from L. groenlandicum Veder; L. columbianum Piper, Ericaceae: Cain, Lynn, J. Am. Pharm. Assoc. 23, 666 (1934); Penfold, J. Proc. R. Soc. N.S.W. 59, 206 (1925). Structure: G. Büchi et al., Tetrahedron Lett. 1959 (no. 6), 14. Stereochemistry: L. Dolejs, F. Sorm, Tetrahedron Lett. 1959 (no. 17), 1; revised stereochemistry: G. Büchi et al., J. Am. Chem. Soc. 91, 6473 (1969).
Properties
Needles from alc, mp 104-105°. Sublimes easily, even below the mp. bp760 292°. nD110 1.4667. [α]D20 +28° (c = 10 in chloroform). Practically insol in water. Sol in alc (about 10% w/v). Soluble in other organic solvents.Derivative
Chromate.C30H50O4Cr; mol wt 526.71.
C 68.41%, H 9.57%, O 12.15%, Cr 9.87%.