L6250

Sigma-Aldrich

Lithocholic acid

≥95%

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/REAXYS Number:
3217757
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25
Pricing and availability is not currently available.

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

human ... POLA1(5422), TOP2A(7153)
rat ... Polb(29240)

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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.

Packaging

10, 25 g in poly bottle

Biochem/physiol Actions

Bile Acid

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. L6250.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
Nathalie Ménard et al.
Pharmaceutical research, 29(7), 1882-1896 (2012-03-28)
Novel surfactants made of diglutamic acid (DG) polar head linked to lithocholic, arachidonic, linoleic or stearic acids were designed for drug solubilization. Surfactants 3-D conformer and packing parameter were determined by molecular modelling and self-assembling properties by pyrene fluorescence measurements....
Articles
The liver excretes excess cholesterol in the form of bile acids. Bile acids serve two purposes: to remove unwanted cholesterol from the body and to aid in lipid digestion in the intestine.
Read More
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.
Read More
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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