| Identification | Back Directory | [Name]
β-Muricholic Acid | [CAS]
2393-59-1 | [Synonyms]
β-Muricholic Acid
3a,6b,7b-Trihydroxy-5b-cholanoic acid
(3α,5β,6β,7β)-3,6,7-Trihydroxycholan-24-oic acid
(3a,5b,6b,7b)-3,6,7-trihydroxy-Cholan-24-oic acid | [Molecular Formula]
C24H40O5 | [MDL Number]
MFCD00271403 | [MOL File]
2393-59-1.mol | [Molecular Weight]
408.58 |
| Chemical Properties | Back Directory | [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 Rotation]
[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| |
| Hazard Information | Back Directory | [Description]
β-Muricholic acid (β-MCA) is a murine-specific primary bile acid.1,2 Dietary administration of β-MCA reduces HMG-CoA reductase activity in liver microsomes from mice fed a high cholesterol and cholic acid diet.3 Dietary administration of β-MCA also dissolves 100% of gallstones in a gallstone-susceptible mouse model of diet-induced cholesterol gallstones.4 | [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 WAHLSTR?M. 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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