Z-Guggulsterone

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Cat.No. 3570 - Z-Guggulsterone | C21H28O2 | CAS No. 39025-23-5
Description: Broad spectrum steroid receptor ligand. More active isomer of guggulsterone (Cat. No. 2013)
Chemical Name: (Z)-Pregna-4,17(20)-diene-3,16-dione
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature

Biological Activity

Broad spectrum steroid receptor ligand; mineralocorticoid, progesterone and glucocorticoid receptor antagonist (Ki values are 37, 224 and 252 nM respectively) and weak androgen receptor agonist (Ki = 315 nM). Induces apoptosis in prostate cancer cells and inhibits angiogenesis via suppression of the VEGF-VEGFR2-Akt signaling 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 (Cat. No. 2013).

Technical Data

M. Wt 312.45
Formula C21H28O2
Storage Store at RT
Purity ≥98% (HPLC)
CAS Number 39025-23-5
PubChem ID 6450278
InChI Key WDXRGPWQVHZTQJ-OSJVMJFVSA-N
Smiles O=C1CC[C@@]2(C)C(CC[C@]3([H])[C@@]([H])2CC[C@@]/4(C)[C@]([H])3CC(C4=C/C)=O)=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 6.25 20mM with gentle warming
ethanol 3.12 10mM with gentle warming

Preparing Stock Solutions

The following data is based on the product molecular weight 312.45. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.2 mL 16 mL 32.01 mL
5 mM 0.64 mL 3.2 mL 6.4 mL
10 mM 0.32 mL 1.6 mL 3.2 mL
50 mM 0.06 mL 0.32 mL 0.64 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Singh et al (2007) Guggulsterone-induced apoptosis in human prostate cancer cells is caused by reactive oxygen intermediate-dependent activation of c-Jun NH2-terminal kinase. Cancer Res. 67 7439 PMID: 17671214

Xiao and Singh (2008) z-Guggulsterone, a constituent of Ayurvedic medicinal plant Commiphora mukul, inhibits angiogenesis in vitro and in vivo. Mol.Cancer Ther. 7 171 PMID: 18202020

Meyer et al (2005) Is antagonism of E/Z-guggulsterone at the farnesoid X receptor mediated by a noncanonical binding site? A molecular modeling study. J.Med.Chem. 48 6955 PMID:


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View Related Products by Target

Keywords: Broad spectrum steroid receptor ligands Nuclear Receptors progesterone mineralocorticoid glucocorticoid Other Nuclear Receptors

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Literature in this Area

Cancer

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