الصفحة الرئيسية>>Signaling Pathways>> Proteases>> Endogenous Metabolite>>β-Muricholic Acid

β-Muricholic Acid (Synonyms: 5β-Cholanic Acid-3α,6β,7β-triol, β-MCA)

رقم الكتالوجGC40719

حمض صفراوي أساسي خاص بالفئران

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β-Muricholic Acid التركيب الكيميائي

Cas No.: 2393-59-1

الحجم السعر المخزون الكميّة
10mM (in 1mL DMSO)
186٫00
متوفر
1mg
90٫00
متوفر
5mg
207٫00
متوفر
10mg
351٫00
متوفر

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Sample solution is provided at 25 µL, 10mM.

Description of β-Muricholic Acid

β-Muricholic acid is a naturally occurring trihydroxy hydrophilic bile acid, as a biliary cholesterol-desaturating agent and facilitates the dissolution of cholesterol gallstones. It found in mice and differs from human primary bile acids by featuring a hydroxyl group in the β- configuration at the 6-position[1-3].

β-muricholic acid(100 µM;48h) inhibited lipid accumulation in primary-cultured mouse hepatocytes after exposure to palmitic acid (PA)/oleic acid (OA), it may be useful in the treatment of nonalcohol fatty liver disease (NAFLD) [4].

β-muricholic acid(0.5% β-muricholic acid in food; p.o; 8 weeks) is more effective than UDCA in enhancing the dissolution rates of cholesterol gallstones via increasing a liquid crystals-containing phase. Addition of beta-muricholic acid decreased gallstone prevalence to 20% through significantly reducing biliary secretion rate, saturation index, and intestinal absorption of cholesterol that prevented the transition of cholesterol from its liquid crystalline phase to solid crystals and stones [5].

[1]. Denk GU, Kleiss CP, et,al. Tauro-β-muricholic acid restricts bile acid-induced hepatocellular apoptosis by preserving the mitochondrial membrane potential. Biochem Biophys Res Commun. 2012 Aug 10;424(4):758-64. doi: 10.1016/j.bbrc.2012.07.029. Epub 2012 Jul 15. PMID: 22809502.
[2]. Montet JC, Parquet M, et,al. beta-Muricholic acid; potentiometric and cholesterol-dissolving properties. Biochim Biophys Acta. 1987 Mar 13;918(1):1-10. doi: 10.1016/0005-2760(87)90002-6. PMID: 3828364.
[3]. Sacquet E, Parquet M, et,al. Metabolism of beta-muricholic acid in man. Steroids. 1985 May;45(5):411-26. doi: 10.1016/0039-128x(85)90006-6. PMID: 3834660.
[4]. Takada S, Matsubara T, et,al. Stress can attenuate hepatic lipid accumulation via elevation of hepatic β-muricholic acid levels in mice with nonalcoholic steatohepatitis. Lab Invest. 2021 Feb;101(2):193-203. doi: 10.1038/s41374-020-00509-x. Epub 2020 Dec 10. PMID: 33303970.
[5]. Wang DQ, Tazuma S. Effect of beta-muricholic acid on the prevention and dissolution of cholesterol gallstones in C57L/J mice. J Lipid Res. 2002 Nov;43(11):1960-8. doi: 10.1194/jlr.m200297-jlr200. PMID: 12401895.

Protocol of β-Muricholic Acid

Cell experiment [1]:

Cell lines

Primary hepatocytes

Preparation Method

Hepatocytes were exposed to 100 µM β-muricholic acid after treatment with palmitic acid (PA)/oleic acid (OA).

Reaction Conditions

100 µM;48h

Applications

β-muricholic acid inhibited lipid accumulation in primary-cultured mouse hepatocytes after exposure to palmitic acid (PA)/oleic acid (OA).

Animal experiment [2]:

Animal models

Male C57L/J mice

Preparation Method

For gallstone dissolution study, mice that have formed cholesterol gallstones were fed chow (control) with or without 0.5% ursodeoxycholic acid (UDCA) or 0.5% β-muricholic acid for 8 weeks.

Dosage form

0.5% β-muricholic acid in food; p.o; 8 weeks

Applications

β-muricholic acid is more effective than UDCA in enhancing the dissolution rates of cholesterol gallstones via increasing a liquid crystals-containing phase.

References:
[1]:Takada S, Matsubara T, et,al. Stress can attenuate hepatic lipid accumulation via elevation of hepatic β-muricholic acid levels in mice with nonalcoholic steatohepatitis. Lab Invest. 2021 Feb;101(2):193-203. doi: 10.1038/s41374-020-00509-x. Epub 2020 Dec 10. PMID: 33303970.
[2]:Wang DQ, Tazuma S. Effect of beta-muricholic acid on the prevention and dissolution of cholesterol gallstones in C57L/J mice. J Lipid Res. 2002 Nov;43(11):1960-8. doi: 10.1194/jlr.m200297-jlr200. PMID: 12401895.

Chemical Properties of β-Muricholic Acid

Cas No. 2393-59-1 SDF
المرادفات 5β-Cholanic Acid-3α,6β,7β-triol, β-MCA
Chemical Name (5β)-3α,6β,7β-trihydroxy-cholan-24-oic acid
Canonical SMILES OC(CC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])[C@@H](O)[C@@H](O)[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O
Formula C24H40O5 M.Wt 408.6
الذوبان 20mg/ml in ethanol & DMSO, 30mg/ml in DMF Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of β-Muricholic Acid

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.4474 mL 12.2369 mL 24.4738 mL
5 mM 0.4895 mL 2.4474 mL 4.8948 mL
10 mM 0.2447 mL 1.2237 mL 2.4474 mL
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In vivo Formulation Calculator (Clear solution) of β-Muricholic Acid

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Average Rating: 5 ★★★★★ (Based on Reviews and 31 reference(s) in Google Scholar.)

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