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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

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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

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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’.

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Customers Also Viewed

Inas Almazari et al.
Topics in current chemistry, 329, 35-60 (2012-08-02)
Guggulsterone (GS) is a phytosterol derived from the gum resin of guggul plants that have been used traditionally to treat various disorders such as burns, wounds, gastric ulcer, cough, gum diseases, urinary complaints, diarrhea, stomach cramps, fascioliasis, and intestinal worms.
Dongfang Yang et al.
Journal of lipid research, 53(3), 529-539 (2012-01-17)
Z-Guggulsterone is a major ingredient in the Indian traditional hypolipidemic remedy guggul. A study in mice has established that its hypolipidemic effect involves the farnesoid X receptor (FXR), presumably by acting as an antagonist of this receptor. It is generally
Dong-Won Ahn et al.
Pancreas, 41(7), 1048-1057 (2012-04-20)
Guggulsterone is a dietary plant sterone possessing therapeutic potential against cancers. However, the antitumor effect of this natural compound on pancreatic cancer has not been determined yet. This study was designed to investigate the therapeutic efficacy of guggulsterone in pancreatic
Rodolfo Gonzalez et al.
Scientific reports, 3, 1463-1463 (2013-03-16)
New small molecules that regulate the step-wise differentiation of human pluripotent stem cells into dopaminergic neurons have been identified. The steroid, guggulsterone, was found to be the most effective inducer of neural stem cells into dopaminergic neurons. These neurons are
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

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