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Merck

G4923

(E)-Guggulsterone

≥95% (HPLC), powder

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C21H28O2
Número CAS:
39025-24-6
Peso molecular:
312.45
NACRES:
NA.77
PubChem Substance ID:
329799934
UNSPSC Code:
12352205
MDL number:
MFCD01310758

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Quality Level

100

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

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 key

WDXRGPWQVHZTQJ-AUKWTSKRSA-N

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

Categorías relacionadas

Biochem/physiol Actions

Naturally occuring bioactive plant sterol isolated from the gum resin of guggul (Commiphora wightii). Antihyperlipidemic. Induces the expression of human CYP3A.
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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H335,H412

Hazard Classifications

Aquatic Chronic 3 - STOT SE 3

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
MKDB0768
MKCX2754
MKCW1298
MKCS1263
MKCN0795

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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
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
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.
Antimo Gioiello et al.
Steroids, 77(3), 250-254 (2011-12-14)
A new stereoselective synthesis of E-guggulsterone is described starting from androsten-3,17-dione. Protection of the ring A enonic system, followed by regioselective Wittig reaction and C-16 oxidation, affords E-guggulsterone in good yields and high stereoselectivity, making this approach easily accessible and
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