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Merck

G4923

Sigma-Aldrich

(E)-Guggulsteron

≥95% (HPLC), powder

Synonym(e):

(17E)-Pregna-4,17(20)-dien-3,16-dion

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About This Item

Empirische Formel (Hill-System):
C21H28O2
CAS-Nummer:
Molekulargewicht:
312.45
MDL-Nummer:
UNSPSC-Code:
12352205
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥95% (HPLC)

Form

powder

Farbe

white to off-white

Löslichkeit

DMSO: soluble 5 mg/mL

Funktionelle Gruppe

ketone

Versandbedingung

ambient

Lagertemp.

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

InChIKey

WDXRGPWQVHZTQJ-AUKWTSKRSA-N

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Biochem./physiol. Wirkung

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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Piktogramme

Exclamation mark

Signalwort

Warning

H-Sätze

Gefahreneinstufungen

Aquatic Chronic 3 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Hyukjae Choi et al.
Journal of natural products, 74(1), 90-94 (2010-12-15)
One isoprenoid, tuberatolide A (1), meroterpenoids tuberatolide B (2) and 2'-epi-tuberatolide B (3), and the known meroterpenoids yezoquinolide (4), (R)-sargachromenol (5), and (S)-sargachromenol (6) were isolated from the Korean marine tunicate Botryllus tuberatus. The structures of these compounds were elucidated
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
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
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
Syed Ghulam Musharraf et al.
Journal of pharmaceutical and biomedical analysis, 56(2), 240-245 (2011-06-17)
A high performance thin-layer chromatographic (HPTLC) method for the simultaneous determination of the hypolipidemic agents, E- and Z-isomers of guggulsterone in Commiphora mukul resin, guggulipid (ethyl acetate extract of resin), and its pharmaceutical formulation, was developed. The developed system was

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