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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:
39025-23-5
Molecular Weight:
312.45
MDL number:
MFCD01310757
UNSPSC Code:
12352200
PubChem Substance ID:
24278392
NACRES:
NA.77

Quality Level

200

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
GHS07

Signal Word

Warning

Hazard Statements

H335

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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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
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
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.
Caroline Scholtes et al.
Therapie, 67(5), 423-427 (2012-12-18)
To test the modulation of farnesoid X receptor activity on the replication of hepatitis C virus in chronically infected patients. This is a proof-of-concept trial that was approved by the ex-French Agency for the Safety of Health Products (ex-Afssaps [currently
Y T Kamal et al.
Biomedical chromatography : BMC, 26(10), 1183-1190 (2012-01-04)
An attempt has been made to develop and validate a simultaneous HPLC method for novel approach of drug release via oil-in-water (o/w) nanoemulsion formulation and Habb-e-Khardal Unani tablet containing piperine and guggul sterones E and Z as main ingredients. Nanoemulsion
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Articles

Bile Acids

The liver excretes excess cholesterol in the form of bile acids. Bile acids serve two purposes: to remove unwanted cholesterol from the body and to aid in lipid digestion in the intestine.

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