Skip to Content
Merck
All Photos(3)

Documents

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C24H40O3
CAS Number:
Molecular Weight:
376.57
Beilstein:
3217757
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25

biological source

bovine bile
synthetic

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

Looking for similar products? Visit Product Comparison Guide

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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.
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
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
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
Alan F Hofmann
Drug metabolism reviews, 36(3-4), 703-722 (2004-11-24)
Lithocholic acid, a monohydroxy, secondary bile acid, is formed by bacterial 7-dehydroxylation of the primary bile acid chenodeoxycholic acid (CDCA) and of the secondary bile acid ursodeoxycholic acid (UDCA). Lithocholic acid and its precursor CDCA are toxic when fed to

Protocols

Investigate bile acid roles in gut hormone profiles and glycemic control, vital for clinical labs exploring potential mechanisms.

Investigate bile acid roles in gut hormone profiles and glycemic control, vital for clinical labs exploring potential mechanisms.

Investigate bile acid roles in gut hormone profiles and glycemic control, vital for clinical labs exploring potential mechanisms.

Investigate bile acid roles in gut hormone profiles and glycemic control, vital for clinical labs exploring potential mechanisms.

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service