Skip to Content
Merck
All Photos(1)

Key Documents

G5168

Sigma-Aldrich

(Z)-Guggulsterone

≥89% (HPLC), powder

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C21H28O2
CAS Number:
Molecular Weight:
312.45
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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

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

InChI key

WDXRGPWQVHZTQJ-OSJVMJFVSA-N

Looking for similar products? Visit Product Comparison Guide

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

Customers Also Viewed

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.
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
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
Dong-Oh Moon et al.
Biochemical pharmacology, 82(11), 1641-1650 (2011-09-10)
Guggulsterone (GGS) has anti-tumor and anti-angiogenesis potential by suppressing nuclear factor-κB and STAT3 activity. Although GGS has been suggested as a potential therapeutic agent for treating various cancers, the underlying molecular mechanisms are unknown. Therefore, we investigated whether GGS sensitizes
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service