Title: Friedelin
CAS Registry Number: 559-74-0
CAS Name: D:A-Friedooleanan-3-one
Additional Names: friedelan-3-one
Molecular Formula: C30H50O
Molecular Weight: 426.72
Percent Composition: C 84.44%, H 11.81%, O 3.75%
Literature References: Major triterpene constituent of cork, obtained by extraction of ground cork with alc. Isoln: Istrati, Ostrogovich, Compt. Rend. 128, 1581 (1899). Isolated also from Ceratopetalum apetalum D. Don, Cunoniaceae: Jefferies, J. Chem. Soc. 1954, 473. Structure, sterochemistry: Brownlie et al., Chem. Ind. (London) 1955, 1156; Kane, Stevenson, Tetrahedron 15, 223 (1961); Stevenson, J. Org. Chem. 28, 188 (1963). Total synthesis of (±)-form: R. E. Ireland, D. M. Walba, Tetrahedron Lett. 1976, 1071.
Properties: Needles from ethyl acetate or alcohol, mp 263-263.5°. [a]D -27.8° (chloroform). One gram dissolves in 8.6 ml chloroform, 264 ml 99% alcohol.
Melting point: mp 263-263.5°
Optical Rotation: [a]D -27.8° (chloroform) |