ChemicalBook > CAS DataBase List > (Z)-Guggulsterone

(Z)-Guggulsterone

Product Name: (Z)-Guggulsterone
CAS No.: 39025-23-5
Chemical Name: (Z)-Guggulsterone
Synonyms: GUGGULSTERONE;GUGULSTERONE;GUGGULSTERONE Z;Z-Gugglesterone;GUGGULESTERONE Z;(Z)-Guggulsterone;CIS GUGGULSTERONE;GUGGULSTERONE Z(P);Guggulsterone Z-RM;GUGGULSTERONE (Z FORM)
CBNumber: CB4309068
Molecular Formula: C21H28O2
Formula Weight: 312.45
MOL File: 39025-23-5.mol

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(Z)-Guggulsterone Property

Melting point:: 188-190°
alpha: D26 -61° (c = 1 in chloroform)
Boiling point:: 463.3±45.0 °C(Predicted)
Density: 1.10±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO: 5 mg/mL
form: powder
color: light yellow
Stability:: 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)

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Safety

Hazard Codes: Xi
Risk Statements: 37-38
Safety Statements: 36
WGK Germany: 3
HS Code: 2914299000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 1302214
Product name: Guggulsterone Z
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 25mg
Price: $485
Updated: 2025/07/31

Sigma-Aldrich

Product number: 78251
Product name: (Z)-Guggulsterone
Purity: analytical standard
Packaging: 10mg
Price: $283
Updated: 2022/05/15

Cayman Chemical

Product number: 71800
Product name: (Z)-Guggulsterone
Packaging: 5mg
Price: $109
Updated: 2024/03/01

Cayman Chemical

Product number: 71800
Product name: (Z)-Guggulsterone
Packaging: 50mg
Price: $849
Updated: 2024/03/01

Sigma-Aldrich

Product number: G5168
Product name: (Z)-Guggulsterone
Purity: ≥89% (HPLC), powder
Packaging: 5mg
Price: $214
Updated: 2025/07/31

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(Z)-Guggulsterone Chemical Properties,Usage,Production

Description

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

Uses

(Z)-Guggulsterone acts as an α-glucosidase inhibitor also known as a hypolipidemic agent.

Uses

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.

Biological Activity

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.

storage

Store at RT

References

[1] NANCY L. URIZAR. A Natural Product That Lowers Cholesterol As an Antagonist Ligand for FXR[J]. Science, 2002, 296 5573. DOI:10.1126/science.1072891
[2] TIANLONG LIU. Z-Guggulsterone attenuates astrocytes-mediated neuroinflammation after ischemia by inhibiting toll-like receptor 4 pathway[J]. Journal of Neurochemistry, 2018, 147 6: 803-815. DOI:10.1111/jnc.14583
[3] ANDREW AGBAY. Guggulsterone-releasing microspheres direct the differentiation of human induced pluripotent stem cells into neural phenotypes.[J]. Biomedical materials (Bristol, England), 2018, 13 3: 034104. DOI:10.1088/1748-605x/aaaa77
[4] FENG-GUO LIU. Z-Guggulsterone Produces Antidepressant-Like Effects in Mice through Activation of the BDNF Signaling Pathway.[J]. International Journal of Neuropsychopharmacology, 2017, 20 6: 485-497. DOI:10.1093/ijnp/pyx009

(Z)-Guggulsterone Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from (Z)-Guggulsterone manufacturers

Career Henan Chemical Co

Product: (E)-Guggulsterone 39025-23-5
Price: US $1.00/KG
Min. Order: 1g
Purity: 99%
Supply Ability: 100KG
Release date: 2018-12-25

39025-23-5, (Z)-GuggulsteroneRelated Search:

METHOPRENE ACID AZ20 Eltanolone 5BETA-PREGNANE-3ALPHA,20ALPHA-DIOL Gestrinone Progesterone Pregnenolone acetate Gestodene Pregnenolone ALKYL KETENE DIMER Minocycline GUGGULSTERONE E Trenbolone DO264 NOTUMib-1 (Z)-Guggulsterone GUGGULSTERONE,CIS GUGGULSTERONE,GUGGULSTERONE Z,GUGGULSTERONE (Z FORM),(Z)-Guggulsterone GUGGULSTERONE Z(PRIMARY STANDARD)

4,17(20)-(CIS)-PREGNADIEN-3,16-DIONE

GUGULSTERONE

GUGGULESTERONE Z

GUGGULSTERONE

GUGGULSTERONE Z

GUGGULSTERONE (Z FORM)

CIS-4,17(20)-PREGNADIENE-3,16-DIONE

CIS GUGGULSTERONE

PREGNA-4,17(20)-DIENE-3,16-DIONE

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

(Z)-Guggulsterone

(17Z)-Pregna-4,17(20)-diene-3,16-dione, 4,17(20)-cis-Pregnadiene-3,16-dione

Z-Gugglesterone

GUGGULSTERONE Z(P)

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

Guggulsterone Z (25 mg)

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

Z-Guggulsterone Z-Guggulsterone HPLC≥90% 39025-23-5 5mg

(8R,9S,10R,13S,14S,Z)-17-ethylidene-10,13-dimethyl-7,8,9,10,11,12,13,14,15,17-decahydro-1H-cyclopenta[a]phenanthrene-3,16(2H,6H)-dione

Guggulsterone Z-RM

(Z)-Guggulsterone, 10 mM in DMSO

39025-23-5

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