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39025-23-5

Supplier Related Products Identification Chemical Properties Safety Data Hazard Information

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Identification

Name
(Z)-Guggulsterone
CAS
39025-23-5
Synonyms
GUGULSTERONE
GUGGULSTERONE
GUGGULSTERONE Z
Z-Gugglesterone
GUGGULESTERONE Z
CIS GUGGULSTERONE
(Z)-Guggulsterone
GUGGULSTERONE Z(P)
GUGGULSTERONE (Z FORM)
Guggulsterone Z (25 mg)
PREGNA-4,17(20)-DIENE-3,16-DIONE
CIS-4,17(20)-PREGNADIENE-3,16-DIONE
4,17(20)-(CIS)-PREGNADIEN-3,16-DIONE
(Z)-Pregna-4,17(20)-diene-3,16-dione
(17Z)-Pregna-4,17(20)-diene-3,16-dione
Pregna-4,17(20)-diene-3,16-dione, (17Z)-
(17Z)-Pregna-4,17(20)-diene-3,16-dione, 4,17(20)-cis-Pregnadiene-3,16-dione
Molecular Formula
C21H28O2
MDL Number
MFCD01310757
MOL File
39025-23-5.mol
Molecular Weight
312.45

Chemical Properties

Melting point 
188-190°
Boiling point 
463.3±45.0 °C(Predicted)
alpha 
D26 -61° (c = 1 in chloroform)
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

Safety Data

Hazard Codes 
Xi
Risk Statements 
37-38
Safety Statements 
36
WGK Germany 
3

HS Code 
2914299000

Hazard Information

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.
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.
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
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