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L6250

Sigma-Aldrich

Lithocholic acid

≥95%

Synonyma:

3α-Hydroxy-5β-cholan-24-oic acid, 3α-Hydroxy-5β-cholanic acid, 5β-Cholan-24-oic acid-3α-ol

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About This Item

Empirický vzorec (Hillův zápis):
C24H40O3
Číslo CAS:
434-13-9
Molekulová hmotnost:
376.57
Beilstein/REAXYS Number:
3217757
EC Number:
207-099-1
MDL number:
MFCD00003682
UNSPSC Code:
12352106
PubChem Substance ID:
24896429
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

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.

Biochem/physiol Actions

Bile Acid

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Osvědčení o analýze (COA)

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Lithocholic acid-2,2,3,4,4-d5 98 atom % D

Sigma-Aldrich

614033

Lithocholic acid-2,2,3,4,4-d5

β-Muricholic Acid ≥98% (HPLC)

Sigma-Aldrich

SML2372

β-Muricholic Acid

Glycoursodeoxycholic acid ≥96.0% (TLC)

Sigma-Aldrich

06863

Glycoursodeoxycholic 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
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
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.
Valeria Tripodi et al.
Annals of hepatology, 11(6), 930-934 (2012-11-01)
Cholestasis leads to liver cell death, fibrosis, cirrhosis, and eventually liver failure. Bile duct ligated rats constitute an interesting model to study the mechanism of cholestasis, and its action on several organs and tissues, including the brain. To analyze brain
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