G5168

(Z)-Guggulsterone

Name: (<I>Z</I>)-Guggulsterone
Brand: SIGMA

≥89% (HPLC), bile acid receptor antagonist, powder

Synonym(s):

(17Z)-Pregna-4,17(20)-diene-3,16-dione, 4,17(20)-trans-Pregnadiene-3,16-dione

Select a Size

All Photos(1)

About This Item

Empirical Formula (Hill Notation):

C₂₁H₂₈O₂

CAS Number:

39025-23-5

Molecular Weight:

312.45

UNSPSC Code:

12352200

PubChem Substance ID:

24278392

NACRES:

NA.77

MDL number:

MFCD01310757

Product Name

(Z)-Guggulsterone, ≥89% (HPLC), powder

SMILES string

[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)\C(=C\C)C(=O)C[C@@]24[H]

InChI key

WDXRGPWQVHZTQJ-OSJVMJFVSA-N

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

assay

≥89% (HPLC)

form

powder

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤5.4% E-form

color

light yellow

solubility

DMSO: 5 mg/mL

application(s)

forensics and toxicology
veterinary

storage temp.

2-8°C

Quality Level

200

Looking for similar products? Visit Product Comparison Guide

Related Categories

Analytical Chemistry

Analytical Chromatography

Bioactive Small Molecules

Chromatography Standards

Reference Materials

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.

(Z)-Guggulsterone is an antagonist ligand for bile acid receptor.

pictograms

GHS07

signalword

Warning

hcodes

H335

pcodes

P261 - P271 - P304 + P340 + P312 - P403 + P233 - P405 - P501

Hazard Classifications

STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Guggulsterone (GS) inhibits smokeless tobacco and nicotine-induced NF-κB and STAT3 pathways in head and neck cancer cells.

Muzafar A Macha et al.

Carcinogenesis, 32(3), 368-380 (2010-12-24)

Understanding the molecular pathways perturbed in smokeless tobacco- (ST) associated head and neck squamous cell carcinoma (HNSCC) is critical for identifying novel complementary agents for effective disease management. Activation of nuclear factor-kappaB (NF-κB) and cyclooxygenase-2 (COX-2) was reported in ST-associated

Inhibition of farnesoid X receptor controls esophageal cancer cell growth in vitro and in nude mouse xenografts.

Baoxiang Guan et al.

Cancer, 119(7), 1321-1329 (2013-01-03)

Gastroesophageal reflux is a risk factor for esophageal adenocarcinoma, and bile acid and its farnesoid X receptor (FXR) have been implicated in esophageal tumorigenesis. The authors investigated the role of FXR expression and activity in esophageal cancer initiation and growth.

Reversion of P-glycoprotein-mediated multidrug resistance by guggulsterone in multidrug-resistant human cancer cell lines.

Hong-Bin Xu et al.

European journal of pharmacology, 694(1-3), 39-44 (2012-09-11)

Multidrug resistance (MDR) presents a serious problem in cancer chemotherapy. Our previous studies have shown that guggulsterone could reverse MDR through inhibiting the function and expression of P-glycoprotein (P-gp). The present study is to further investigate the reversal effects of

Guggulsterone inhibits melanogenesis in B16 murine melanoma cells by downregulating tyrosinase expression.

Jeung-Hyun Koo et al.

International journal of molecular medicine, 30(4), 974-978 (2012-07-17)

In the present study, we investigated the effect of guggulsterone on melanogenesis in B16 melanoma cells and elucidated its possible mechanism of action. The effects of guggulsterone on melanogenesis were determined by assaying melanin synthesis and cellular tyrosinase activity in

Simultaneous estimation of E- and Z-isomers of guggulsterone in rabbit plasma using liquid chromatography tandem mass spectrometry and its application to pharmacokinetic study.

R S Bhatta et al.

Biomedical chromatography : BMC, 25(9), 1054-1060 (2011-01-27)

A sensitive and selective liquid chromatography/tandem mass spectrometric method was developed for simultaneous determination of E- and Z-guggulsterone isomers (antihyperlipidemic drug) in rabbit plasma. Both the isomers were resolved on a Symmetry-Shield C(18) (5 µm, 4.6 × 150 mm) column, using gradient

View All Related Papers