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Merck

G4923

(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
NACRES:
NA.77
PubChem Substance ID:
329799934
UNSPSC Code:
12352205
MDL number:
MFCD01310758

Key Documents

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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

Related Categories

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H335,H412

Hazard Classifications

Aquatic Chronic 3 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (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
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
Hong-Bin Xu et al.
European journal of pharmacology, 694(1-3), 39-44 (2012-09-11)
Multidrug resistance (MDR) presents a serious problem in cancer chemotherapy. Our previous studies have shown that guggulsterone could reverse MDR through inhibiting the function and expression of P-glycoprotein (P-gp). The present study is to further investigate the reversal effects of
Baoxiang Guan et al.
Cancer, 119(7), 1321-1329 (2013-01-03)
Gastroesophageal reflux is a risk factor for esophageal adenocarcinoma, and bile acid and its farnesoid X receptor (FXR) have been implicated in esophageal tumorigenesis. The authors investigated the role of FXR expression and activity in esophageal cancer initiation and growth.
Muzafar A Macha et al.
Carcinogenesis, 32(3), 368-380 (2010-12-24)
Understanding the molecular pathways perturbed in smokeless tobacco- (ST) associated head and neck squamous cell carcinoma (HNSCC) is critical for identifying novel complementary agents for effective disease management. Activation of nuclear factor-kappaB (NF-κB) and cyclooxygenase-2 (COX-2) was reported in ST-associated
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