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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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Description
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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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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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