β-Muricholic Acid

Product Nameβ-Muricholic Acid
CAS2393-59-1
MFC24H40O5
MW408.58
EINECS
MOL File2393-59-1.mol

Chemical Properties

Melting point	226 °C
Boiling point	565.7±40.0 °C(Predicted)
Density	1.184±0.06 g/cm3(Predicted)
storage temp.	-20°C
solubility	DMSO (Slightly), Ethanol (Slightly,Sonicated), Methanol (Slightly), Water (Sligh
form	powder
pka	4.76±0.10(Predicted)
color	white to beige
optical activity	[α]/D +59 to +65°, c = 0.1 in methanol
InChIKey	DKPMWHFRUGMUKF-UINRVLNBNA-N
SMILES	C[C@]12CC[C@@H](O)C[C@@]1([H])[C@H](O)[C@H](O)[C@@]1([H])[C@]3([H])CC[C@]([H])([C@H](C)CCC(=O)O)[C@@]3(C)CC[C@]21[H] \|&1:1,4,7,9,11,13,15,19,21,28,32,r\|

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Description

β-Muricholic acid (β-MCA) is a murine-specific primary bile acid. Dietary administration of β-MCA reduces HMG-CoA reductase activity in liver microsomes from mice fed a high cholesterol and cholic acid diet. Dietary administration of β-MCA also dissolves 100% of gallstones in a gallstone-susceptible mouse model of diet-induced cholesterol gallstones.

Uses

β-Muricholic Acid is an bile acid found in urine. β-Muricholic Acid has been used in studies of down regulation of transporter protein through ubiquitin dependent protein degradation.

Definition

ChEBI: Beta-muricholic acid is a member of the class of muricholic acids in which the hydroxy groups at positions 6 and 7 both have beta configuration. It is a member of muricholic acids, a 6beta-hydroxy steroid and a 7beta-hydroxy steroid. It is a conjugate acid of a beta-muricholate.

in vivo

β-Muricholic acid (Fed chow with 0.5% β-muricholic acid for 8 weeks) prevents diet-induced or experimental cholesterol gallstones in mice^[2].

Animal Model:	6-8 weeks, Male C57L/J mice (with a lithogenic diet (2% cholesterol and 0.5% cholic acid))^[2]
Dosage:	0.5% β-muricholic acid
Administration:	Fed chow with 0.5% β-muricholic acid for 8 weeks
Result:	Decreased gallstone prevalence to 20% through significantly reducing biliary secretion rate, saturation index, and intestinal absorption of cholesterol, as well as inducing phase boundary shift and an enlarged Region E that prevented the transition of cholesterol from its liquid crystalline phase to solid crystals and stones.

References

[1] ANNIKA WAHLSTRM. Intestinal Crosstalk between Bile Acids and Microbiota and Its Impact on Host Metabolism.[J]. Cell metabolism, 2016, 24 1: 41-50. DOI: 10.1016/j.cmet.2016.05.005
[2] YUKIO FUJINO . Suppression of Hepatic HMG-CoA Reductase Activity by β-Muricholic Acid in Mice Fed a Diet Containing Cholesterol and Cholic Acid[J]. Japanese journal of pharmacology, 1988, 46 4: Pages 421-423. DOI: 10.1016/s0021-5198(19)43298-8
[3] DAVID Q-H WANG Susumu T. Effect of beta-muricholic acid on the prevention and dissolution of cholesterol gallstones in C57L/J mice.[J]. Journal of Lipid Research, 2002, 43 11: 1960-1968. DOI: 10.1194/jlr.m200297-jlr200

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