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G5168

Sigma-Aldrich

(Z)-Guggulsterone

≥89% (HPLC), powder

Synonyma:

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

Přihlásitk zobrazení cen stanovených pro organizaci a smluvních cen
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About This Item

Empirický vzorec (Hillův zápis):
C21H28O2
Číslo CAS:
39025-23-5
Molekulová hmotnost:
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

signalword

Warning

hcodes

H335

Hazard Classifications

STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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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
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
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
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
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