Title: Taraxerol
CAS Registry Number: 127-22-0
CAS Name: (3b)-D-Friedoolean-14-en-3-ol
Additional Names: isoolean-14-en-3b-ol; skimmiol; alnulin; tiliadin
Molecular Formula: C30H50O
Molecular Weight: 426.72
Percent Composition: C 84.44%, H 11.81%, O 3.75%
Literature References: Found in Tilia cordata Mill., Tiliaceae: Bräutigam, Arch. Pharm. 238, 555 (1900); in Alnus glutinosa (L.) Gaertn., Betulaceae: Zellner, Weiss, Sitzungsber. Akad. Wiss. Wien 132, 258 (1923); in Taraxacum officinale Weber, Compositae: Burrows, Simpson, J. Chem. Soc. 1938, 2042; in Litsea dealbata Nees, Lauraceae: Dunstan et al., Aust. J. Chem. 6, 321 (1953); from Befaria racemosa (Vent.), Ericaceae: Euda et al., J. Org. Chem. 26, 271 (1961). Structure: Beaton et al., J. Chem. Soc. 1955, 2131. Partial synthesis from b-amyrin: eidem, Chem. Ind. (London) 1955, 35.
Properties: Plates from chloroform + methanol, needles from benzene, mp 282-285°. uv max (ethanol): 210, 215, 220, 223 nm (e 3900, 2400, 700, 250). Sol in benzene, chloroform, ether, ethyl acetate, acetic anhydride, acetic acid, phenol, pyridine, xylene; less sol in alcohol.
Melting point: mp 282-285°
Absorption maximum: uv max (ethanol): 210, 215, 220, 223 nm (e 3900, 2400, 700, 250)
Derivative Type: Acetate
Molecular Formula: C32H52O2
Molecular Weight: 468.75
Percent Composition: C 81.99%, H 11.18%, O 6.83%
Properties: Plates from chloroform + methanol, mp 303-305°. [a]D +10.5° (c = 1.8 in chloroform).
Melting point: mp 303-305°
Optical Rotation: [a]D +10.5° (c = 1.8 in chloroform)
Derivative Type: Benzoate
Molecular Formula: C37H54O2
Molecular Weight: 530.82
Percent Composition: C 83.72%, H 10.25%, O 6.03%
Properties: Needles from benzene or chloroform + alc, mp 292-293°. [a]D23 +35.7° (c = 0.7 in chloroform).
Melting point: mp 292-293°
Optical Rotation: [a]D23 +35.7° (c = 0.7 in chloroform)
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