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(E)-Guggulsterone
Cayman Chemical Item Number 10011296
Description
Bile acids are essential for solubilization and transport of dietary lipids, are the major products of cholesterol catabolism, and are physiological ligands for farnesoid X receptor (FXR), a nuclear receptor that regulates genes involved in lipid metabolism.1↗ They are also inherently cytotoxic, as physiological imbalance contributes to increased oxidative stress.2↗,3↗ Bile acid-controlled signaling pathways are promising novel targets to treat such metabolic diseases as obesity, type II diabetes, hyperlipidemia, and atherosclerosis. Guggulsterone, derived from resin of the guggul tree, is a competitive antagonist of FXR both in vitro and in vivo.4↗ The cis stereoisomer of guggulsterone, (E)-guggulsterone, decreases chenodeoxycholic acid (CDCA)-induced FXR activation with an IC50 value of 15 µM. 5↗,6↗ By inhibiting CDCA-induced transactivation of FXR, guggulsterone lowers low-density lipoprotein cholesterol and triglyceride levels in rodents fed a high cholesterol diet.4↗
Formal Name pregna-4-17(20)-diene-3,16-dione
CAS Number 39025-24-6
Molecular Formula C21H28O2
Formula Weight 312.5
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES O=C1CC[C@@]2(C)C(CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC(/C4=C\C)=O)=C1
InCHI Code 1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4+/t15-,17+,18+,20+,21-/m1/s1
InCHI Key WDXRGPWQVHZTQJ-OSJVMJFVSA-N |