Title: Guggulsterone
CAS Registry Number: 95975-55-6
CAS Name: Pregna-4,17(20)-diene-3,16-dione
Molecular Formula: C21H28O2
Molecular Weight: 312.45
Percent Composition: C 80.72%, H 9.03%, O 10.24%
Literature References: Bioactive component in guggulu,
q.v., the gum resin of the Ayurvedic medicinal plant,
Commiphora mukul, Burseraceae, used in treatment of lipid disorders. Both the
E- and
Z- isomers are naturally occurring and bioactive. Synthesis and stereochemistry: W. R. Benn, R. M. Dodson,
J. Org. Chem. 29, 1142 (1964). Isoln from guggulu: V. D. Patil
et al., Tetrahedron 28, 2341 (1972). HPLC determn of isomers in serum: N. Verma
et al., J. Chromatogr. B 708, 243 (1998). LC determn of isomers in commercial guggulu formulations: M. Nagarajan
et al., J. AOAC Int. 84, 24 (2001). Inhibition of the bile acid receptor FXR and cholesterol lowering activity: N. L. Urizar
et al., Science 296, 1703 (2002). Brief review of proposed mechanism of action: C. J. Sinal, F. J. Gonzalez,
Trends Endocrinol. Metab. 13, 275-276 (2002).
Derivative Type: E-Form
CAS Registry Number: 39025-24-6
Properties: Prisms from aq methanol, mp 170-171.5°. [a]D26 -30° (c = 1 in chloroform). uv max (methanol): 241 nm (e 27600).
Melting point: mp 170-171.5°
Optical Rotation: [a]D26 -30° (c = 1 in chloroform)
Absorption maximum: uv max (methanol): 241 nm (e 27600)
Derivative Type: Z-Form
CAS Registry Number: 39025-23-5
Properties: Crystals from aq methanol, mp 188-190°. [a]D26 -61° (c = 1 in chloroform). uv max (methanol): 241 nm (e 25000).
Melting point: mp 188-190°
Optical Rotation: [a]D26 -61° (c = 1 in chloroform)
Absorption maximum: uv max (methanol): 241 nm (e 25000)
