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ChemicalBook > Product Catalogue >Biochemical Engineering >Plant extracts >(Z)-Guggulsterone

(Z)-Guggulsterone

(Z)-Guggulsterone Structure
  • ₹23490.25 - ₹83688.08
  • Product name: (Z)-Guggulsterone
  • CAS: 39025-23-5
  • MF: C21H28O2
  • MW: 312.45
  • EINECS:
  • MDL Number:MFCD01310757
  • 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
3 prices
Selected condition:

Brand

  • Sigma-Aldrich(India)

Package

  • 5MG
  • 10MG
  • 25MG
  • ManufacturerSigma-Aldrich(India)
  • Product numberG5168
  • Product description(Z)-Guggulsterone ≥89% (HPLC), powder
  • Packaging5MG
  • Price₹23490.25
  • Updated2022-06-14
  • Buy
  • ManufacturerSigma-Aldrich(India)
  • Product number78251
  • Product description(Z)-Guggulsterone analytical standard
  • Packaging10MG
  • Price₹24540.28
  • Updated2022-06-14
  • Buy
  • ManufacturerSigma-Aldrich(India)
  • Product numberG5168
  • Product description(Z)-Guggulsterone ≥89% (HPLC), powder
  • Packaging25MG
  • Price₹83688.08
  • Updated2022-06-14
  • Buy
Manufacturer Product number Product description Packaging Price Updated Buy
Sigma-Aldrich(India) G5168 (Z)-Guggulsterone ≥89% (HPLC), powder 5MG ₹23490.25 2022-06-14 Buy
Sigma-Aldrich(India) 78251 (Z)-Guggulsterone analytical standard 10MG ₹24540.28 2022-06-14 Buy
Sigma-Aldrich(India) G5168 (Z)-Guggulsterone ≥89% (HPLC), powder 25MG ₹83688.08 2022-06-14 Buy

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.
InChI :InChI=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
InChIKey :WDXRGPWQVHZTQJ-OSJVMJFVSA-N
SMILES :C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)/C(=C/C)/C(=O)C3)CC2
LogP :3.650 (est)

Safety Information

Symbol(GHS): GHS hazard pictograms
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning GHS hazard pictograms
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P271 Use only outdoors or in a well-ventilated area.
P403+P233 Store in a well-ventilated place. Keep container tightly closed.
P405 Store locked up.
P501 Dispose of contents/container to..…

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. They are also inherently cytotoxic, as physiological imbalance contributes to increased oxidative stress. 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. The trans stereoisomer of guggulsterone, (Z)-guggulsterone, decreases chenodeoxycholic acid (CDCA)-induced FXR activation with an IC50 value of 17 μM. By inhibiting CDCA-induced transactivation of FXR, guggulsterone lowers low-density lipoprotein cholesterol and triglyceride levels in rodents fed a high cholesterol diet. While both cis and trans stereoisomers have been shown to directly decrease hepatic cholesterol, the Z isomer is the most studied. (Z)-Guggulsterone demonstrates antitumor-promoting effects inhibiting both constitutive and interleukin-6-induced STAT3 activation in human multiple myeloma cells and suppressing the VEGF-VEGF/R2-Akt signaling axis in DU145 human prostate cancer cells.

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