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G4923

Sigma-Aldrich

(E)-Guggulsterone

≥95% (HPLC), powder

Synonym(s):

(17E)-Pregna-4,17(20)-diene-3,16-dione

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About This Item

Empirical Formula (Hill Notation):
C21H28O2
CAS Number:
39025-24-6
Molecular Weight:
312.45
MDL number:
MFCD01310758
UNSPSC Code:
12352205
PubChem Substance ID:
329799934
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: soluble 5 mg/mL

functional group

ketone

shipped in

ambient

storage temp.

2-8°C

SMILES string

C\C=C1\C(=O)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

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-AUKWTSKRSA-N

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Biochem/physiol Actions

Naturally occuring bioactive plant sterol isolated from the gum resin of guggul (Commiphora wightii). Antihyperlipidemic. Induces the expression of human CYP3A.. Guggulsterone potently reverses multi-drug resistance in a number of human cancer cell lines, extending the efficacy of chemotherapy.

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H335,H412

Hazard Classifications

Aquatic Chronic 3 - 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

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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Sang-Jip Nam et al.
Journal of natural products, 70(11), 1691-1695 (2007-11-09)
Three new scalarane-based sesterterpenes, 1- 3, were isolated from a marine sponge of the genus Spongia, and their chemical structures were elucidated by analysis of HRMS and 2-D NMR spectra. The isolated compounds 1 and 3 showed inhibition against the
Jae-Jun Song et al.
International journal of pediatric otorhinolaryngology, 74(12), 1384-1387 (2010-10-26)
Guggulsterone is a bioactive constituent of resinous sap originating from the guggul tree, Commiphora mukul, which has been used over several thousands of years to treat various diseases, including atherosclerosis, rheumatism, and obesity. However, the effect of guggulsterone inflammatory reactions
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
Chunhua Zhu et al.
Lipids in health and disease, 10, 199-199 (2011-11-08)
Apolipoprotein M (apoM) may have potential antiatherosclerotic properties. It has been reported that apoM expression could be regulated by many intracellar and extracellar factors. In the present study we further investigated regulation of apoM expression in Caco-2 cells stimulated by
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