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L6250

Sigma-Aldrich

Lithocholic acid

≥95%

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Synonym(s):
3α-Hydroxy-5β-cholan-24-oic acid, 3α-Hydroxy-5β-cholanic acid, 5β-Cholan-24-oic acid-3α-ol
Empirical Formula (Hill Notation):
C24H40O3
CAS Number:
Molecular Weight:
376.57
Beilstein:
3217757
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

bovine bile
synthetic

Quality Level

Assay

≥95%

mol wt

376.57 g/mol

mp

183-188 °C (lit.)

functional group

carboxylic acid

shipped in

ambient

storage temp.

room temp

SMILES string

[H][C@]12CC[C@@]3([H])[C@]4([H])CC[C@H]([C@H](C)CCC(O)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2

InChI

1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1

InChI key

SMEROWZSTRWXGI-HVATVPOCSA-N

Gene Information

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This Item
T4009C1129C9377
Lithocholic acid ≥95%

Sigma-Aldrich

L6250

Lithocholic acid

Cholic acid from bovine and/or ovine, ≥98%

Sigma-Aldrich

C1129

Cholic acid

Chenodeoxycholic acid

Sigma-Aldrich

C9377

Chenodeoxycholic acid

assay

≥95%

assay

≥95% (HPLC)

assay

≥98%

assay

-

mol wt

376.57 g/mol

mol wt

micellar avg mol wt 2100

mol wt

408.57 g/mol

mol wt

392.57 g/mol

mp

183-188 °C (lit.)

mp

-

mp

200-201 °C (lit.)

mp

165-167 °C (lit.)

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

functional group

carboxylic acid

functional group

sulfonic acid

functional group

carboxylic acid

functional group

carboxylic acid

General description

Lithocholic acid is an oligo(ethylene glycol) derivative of bile acid.

Application

Lithocholic acid has been used in a study to assess cholestasis and its action on several organs and tissues in rats. It has also been used in a study to investigate the regulation of hepatic phospholipid and bile acid homeostasis through SMAD3 activation by TGFβ.

Biochem/physiol Actions

Bile Acid

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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25G
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β-Muricholic Acid ≥98% (HPLC)

Sigma-Aldrich

SML2372

β-Muricholic Acid

Katarzyna Magiera et al.
Cell chemical biology, 24(4), 458-470 (2017-03-28)
USP2a is a deubiquitinase responsible for stabilization of cyclin D1, a crucial regulator of cell-cycle progression and a proto-oncoprotein overexpressed in numerous cancer types. Here we report that lithocholic acid (LCA) derivatives are inhibitors of USP proteins, including USP2a. The
Vincent R Richard et al.
Aging, 5(4), 234-269 (2013-04-05)
Macromitophagy controls mitochondrial quality and quantity. It involves the sequestration of dysfunctional or excessive mitochondria within double-membrane autophagosomes, which then fuse with the vacuole/lysosome to deliver these mitochondria for degradation. To investigate a physiological role of macromitophagy in yeast, we
Claudiu Saracut et al.
Acta cirurgica brasileira, 30(9), 624-631 (2015-10-16)
To assess whether deoxycholic acid (DOC) and lithocholic acid (LCA) administered in a period of six months in a concentration of 0.25% may have a carcinogenic role in mice colon. The study used C57BL6 female mice divided into four groups.
Satu Strandman et al.
The journal of physical chemistry. B, 117(1), 252-258 (2012-12-12)
Thermoresponsive characteristics of oligo(ethylene glycol) derivatives of lithocholic acid (LCA) depend on the hydrophilic/hydrophobic balance of the compounds. Below a threshold temperature (∼30 °C), one of the derivatives, LCA(EG(4))(2), self-assembles in water into hollow nanotubes that form thixotropic gels at
Yuan Chen et al.
Molecular endocrinology (Baltimore, Md.), 29(4), 613-626 (2015-02-13)
Among diseases unique to pregnancy, intrahepatic cholestasis of pregnancy is the most prevalent disorder with elevated serum bile acid levels. We have previously shown that estrogen 17β-estradiol (E2) transrepresses bile salt export pump (BSEP) through an interaction between estrogen receptor

Protocols

This method is particularly useful in research into the role of individual bile acids as signaling molecules; suitable for clinical laboratories to investigate potential mechanisms linked to gut hormone profiles and glycemic control.

Related Content

Bile Acids (BA) are synthesized in the liver and play important roles in cholesterol homeostasis, absorption of vitamins and lipids, and various key metabolic processes.

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