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SML2372

Sigma-Aldrich

β-Muricholic Acid

≥98% (HPLC)

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Synonym(s):
β-MCA, (3a,5b,6b,7b)-3,6,7-trihydroxy-cholan-24-oic acid, 5β-Cholanic acid-3α,6β,7β-triol, beta-Muricholic Acid
Empirical Formula (Hill Notation):
C24H40O5
CAS Number:
2393-59-1
Molecular Weight:
408.57
MDL number:
MFCD00271403
UNSPSC Code:
12352106
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +59 to +65°, c = 0.5 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

InChI

1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13?,14-,15?,16?,17?,18+,20?,21+,22-,23-,24-/m1/s1

InChI key

DKPMWHFRUGMUKF-CWNVCPLQSA-N

Related Categories

Application

β-Muricholic Acid has been used as a bile acid to study its effects on the expression of pluripotency, stemness, and inflammatory genes in primary mouse hepatocytes (PMH) and tumor-initiating stem-like cells(TICs). It has also been used as a bile acid to study its effects on gut transit ingnotobiotic or conventional mouse models.

Biochem/physiol Actions

β-Muricholic Acid is a naturally occurring trihydroxy hydrophilic bile acid that is produced in the liver of murine. It serves as a biliary cholesterol-desaturating agent and aids in the dissolution of cholesterol gallstones.
β-Muricholic acid (β-MCA) is a natural murine-specific bile acid. β-Muricholic acid has been shown to reduce the absorption of cholesterol. It also has some activity as a farnesoid X receptor antagonist.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Laura Conde de la Rosa et al.
Journal of hepatology, 74(6), 1429-1441 (2021-01-31)
Besides their physiological role in bile formation and fat digestion, bile acids (BAs) synthesised from cholesterol in hepatocytes act as signalling molecules that modulate hepatocellular carcinoma (HCC). Trafficking of cholesterol to mitochondria through steroidogenic acute regulatory protein 1 (STARD1) is
Kyosuke Fujita et al.
Lipids, 52(4), 335-344 (2017-03-21)
The farnesoid X receptor (FXR) is a major nuclear receptor of bile acids; its activation suppresses sterol regulatory element-binding protein 1c (SREBP1c)-mediated lipogenesis and decreases the lipid contents in the liver. There are many reports showing that the administration of
Ylva Bonde et al.
PloS one, 11(1), e0147772-e0147772 (2016-01-30)
High endogenous production of, or treatment with muricholic bile acids, strongly reduces the absorption of cholesterol. Mice abundant in muricholic bile acids may therefore display an increased resistance against dietary induced weight gain, steatosis, and glucose intolerance due to an
David Q-H Wang et al.
Journal of lipid research, 43(11), 1960-1968 (2002-10-29)
This study investigated whether beta-muricholic acid, a natural trihydroxy hydrophilic bile acid of rodents, acts as a biliary cholesterol-desaturating agent to prevent cholesterol gallstones and if it facilitates the dissolution of gallstones compared with ursodeoxycholic acid (UDCA). For gallstone prevention
Xiaobei Pan et al.
Metabolites, 7(2) (2017-06-21)
Certain endogenous bile acids have been proposed as potential therapies for ameliorating Alzheimer's disease (AD) but their role, if any, in the pathophysiology of this disease is not currently known. Given recent evidence of bile acids having protective and anti-inflammatory
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