(Z)-Guggulsterone

Bezeichnung:(Z)-Guggulsterone

CAS-Nr39025-23-5

Englisch Name:(Z)-Guggulsterone

CBNumberCB4309068

SummenformelC21H28O2

Molgewicht312.45

MOL-Datei39025-23-5.mol

(Z)-Guggulsterone physikalisch-chemischer Eigenschaften

Schmelzpunkt	188-190°
alpha	D26 -61° (c = 1 in chloroform)
Siedepunkt	463.3±45.0 °C(Predicted)
Dichte	1.10±0.1 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	DMSO: 5 mg/mL
Aggregatzustand	powder
Farbe	light yellow
Stabilität	Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChI	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-OSJVMJFVSA-N
SMILES	C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)/C(=C/C)/C(=O)C3)CC2
LogP	3.650 (est)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	37-38
S-Sätze:	36
WGK Germany	3
HS Code	2914299000

Gefahreninformationscode (GHS)

(Z)-Guggulsterone Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R37:Reizt die Atmungsorgane.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Guggulsterone-(Z) (39025-23-5) is a natural steroid from?Commiphora mukul?extract (guggulipid) which lowers cholesterol and acts as an FXR antagonist.1?Attenuates astrocyte-mediated neuroinflammation.2? Induces differentiation of pluripotent stem cells to dopaminergic neurons.3 Produces antidepressant-like effects via activation of the BDNF signaling pathway in mouse models.4
Verwenden
(Z)-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.
Verwenden
Z-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.
Definition
ChEBI: Guggulsterone is a 3-hydroxy steroid. It has a role as an androgen.
Biologische Aktivität
Broad spectrum steroid receptor ligand; mineralocorticoid, progesterone and glucocorticoid receptor antagonist (K i values are 37, 224 and 252 nM respectively) and weak androgen receptor agonist (K i = 315 nM). Induces apoptosis in prostate cancer cells and inhibits angiogenesis via suppression of the VEGF-VEGFR2-Akt signalling pathway. Exhibits antilipidemic activity via antagonism of the farnesoid X receptor (FXR) and displays antiseptic, antirheumatic and anti-inflammatory activity in vivo . More active isomer of Guggulsterone (Pregna-4,17(20)-diene-3,16-dione ).
Biochem/physiol Actions
(Z)-Guggulsterone is a natural product that lowers cholesterol due to its function as an antagonist ligand for the bile acid receptor. (Z)-Guggulsterone is a nuclear hormone receptor that regulates the transcription of several genes involved in cholesterol metabolism and plays a role in cholesterol level regulation. (Z)-Guggulsterone is also a selective farnesoid X receptor (FXR) modulator.
Lager
Store at RT
Einzelnachweise
1) Urizar?et al.?(2002),?A Natural Product That Lowers Cholesterol as an Antagonist Ligand for FXR; Science,?296?1703 2) Liu?et al.?(2018),?Z-Guggulsterone attenuates astrocytes-mediated neuroinflammation after ischemia by inhibiting toll-like receptor 4 pathway; J. Neurochem.,?147?803 3) Agbay?et al.?(2018),?Guggulsterone-releasing Microspheres Direct the Differentiation of Human Induced Pluripotent Stem Cells Into Neural Phenotypes; Biomed. Mater.,?13?034104 4) Liu?et al.?(2017),?Z-Guggulsterone Produces Antidepressant-Like Effects in Mice through Activation of the BDNF Signaling Pathway; Int. J. Neuropsychopharmacol.,?20?485

(Z)-Guggulsterone Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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