Cholestenone

Cholestenone (4-cholesten-3-one) is an orally available antimicrobial agent that is metabolized primarily in the liver as an intermediate oxidation product of cholesterol. Cholestenone inhibits human dermal fibroblast migration and fights Helicobacter pylori infection in vitro and in mouse models by inhibiting cholesterol-α-D-glucopyranoside (CGL) . Cholestenone also alleviates metabolic disorders caused by obesity in db/db mice[1][2][3][4].

Product Specifications

CAS Number

[601-57-0]

Product Name Alternative

4-Cholesten-3-one

UNSPSC

12352211

Hazard Statement

H302, H315, H319, H335

Target

Endogenous Metabolite

Type

Natural Products

Related Pathways

Metabolic Enzyme/Protease

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Infection; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/Cholestenone.html

Purity

99.81

Solubility

DMSO : 2 mg/mL (ultrasonic; warming; heat to 60°C) |Ethanol : 50 mg/mL (ultrasonic)

Smiles

CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O

Molecular Formula

C27H44O

Molecular Weight

384.64

Precautions

H302, H315, H319, H335

References & Citations

[1]unichi Kobayashi, et al. Cholestenone functions as an antibiotic against Helicobacter pylori by inhibiting biosynthesis of the cell wall component CGL. Proc Natl Acad Sci U S A. 2021 Apr 20;118 (16) :e2016469118.|[2]Maarit Neuvonen, et al. Enzymatic oxidation of cholesterol: properties and functional effects of cholestenone in cell membranes. 2014 Aug 26;9 (8) :e103743.|[3]G M TOMKINS, et al. Use of delta 4-cholestenone to reduce the level of serum cholesterol in man. Science. 1957 May 10;125 (3254) :936-7.|[4]Mina Higuchi, et al. Dietary Cholest-4-en-3-one, a Cholesterol Metabolite of Gut Microbiota, Alleviates Hyperlipidemia, Hepatic Cholesterol Accumulation, and Hyperinsulinemia in Obese, Diabetic db/db Mice. Metabolites. 2024 Jun 3;14 (6) :321.