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| | (Z)-Guggulsterone Basic information |
| Product Name: | (Z)-Guggulsterone | | Synonyms: | 4,17(20)-(CIS)-PREGNADIEN-3,16-DIONE;GUGULSTERONE;GUGGULESTERONE Z;GUGGULSTERONE Z;GUGGULSTERONE (Z FORM);CIS-4,17(20)-PREGNADIENE-3,16-DIONE;CIS GUGGULSTERONE;PREGNA-4,17(20)-DIENE-3,16-DIONE | | CAS: | 39025-23-5 | | MF: | C21H28O2 | | MW: | 312.45 | | EINECS: | | | Product Categories: | | | Mol File: | 39025-23-5.mol |  |
| | (Z)-Guggulsterone Chemical Properties |
| Melting point | 188-190° | | alpha | D26 -61° (c = 1 in chloroform) | | Boiling point | 463.3±45.0 °C(Predicted) | | density | 1.10±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | DMSO: 5 mg/mL | | form | powder | | color | light yellow | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. | | InChIKey | WDXRGPWQVHZTQJ-OSJVMJFVSA-N | | LogP | 3.650 (est) |
| Hazard Codes | Xi | | Risk Statements | 37-38 | | Safety Statements | 36 | | WGK Germany | 3 | | HS Code | 2914299000 |
| | (Z)-Guggulsterone Usage And Synthesis |
| Description | Guggulsterone-(Z) (39025-23-5) is a natural steroid from?Commiphora mukul?extract (guggulipid) which lowers cholesterol and acts as an FXR antagonist.1?Attenuates astrocyte-mediated neuroinflammation.2? Induces differentiation of pluripotent stem cells to dopaminergic neurons.3 Produces antidepressant-like effects via activation of the BDNF signaling pathway in mouse models.4 | | Uses | Z-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent. | | Uses | (Z)-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent. | | Definition | ChEBI: Guggulsterone is a 3-hydroxy steroid. It has a role as an androgen. | | Biological Activity | Broad spectrum steroid receptor ligand; mineralocorticoid, progesterone and glucocorticoid receptor antagonist (K i values are 37, 224 and 252 nM respectively) and weak androgen receptor agonist (K i = 315 nM). Induces apoptosis in prostate cancer cells and inhibits angiogenesis via suppression of the VEGF-VEGFR2-Akt signalling pathway. Exhibits antilipidemic activity via antagonism of the farnesoid X receptor (FXR) and displays antiseptic, antirheumatic and anti-inflammatory activity in vivo . More active isomer of Guggulsterone (Pregna-4,17(20)-diene-3,16-dione ). | | Biochem/physiol Actions | (Z)-Guggulsterone is a natural product that lowers cholesterol due to its function as an antagonist ligand for the bile acid receptor. (Z)-Guggulsterone is a nuclear hormone receptor that regulates the transcription of several genes involved in cholesterol metabolism and plays a role in cholesterol level regulation. (Z)-Guggulsterone is also a selective farnesoid X receptor (FXR) modulator. | | storage | Store at RT | | References | 1) Urizar?et al.?(2002),?A Natural Product That Lowers Cholesterol as an Antagonist Ligand for FXR; Science,?296?1703
2) Liu?et al.?(2018),?Z-Guggulsterone attenuates astrocytes-mediated neuroinflammation after ischemia by inhibiting toll-like receptor 4 pathway; J. Neurochem.,?147?803
3) Agbay?et al.?(2018),?Guggulsterone-releasing Microspheres Direct the Differentiation of Human Induced Pluripotent Stem Cells Into Neural Phenotypes; Biomed. Mater.,?13?034104
4) Liu?et al.?(2017),?Z-Guggulsterone Produces Antidepressant-Like Effects in Mice through Activation of the BDNF Signaling Pathway; Int. J. Neuropsychopharmacol.,?20?485 |
| | (Z)-Guggulsterone Preparation Products And Raw materials |
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