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L6250

Sigma-Aldrich

Lithocholic acid

≥95%

Synonyme(s) :

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

Formule empirique (notation de Hill):
C24H40O3
Numéro CAS:
434-13-9
Poids moléculaire :
376.57
Numéro Beilstein :
3217757
Numéro CE :
207-099-1
Numéro MDL:
MFCD00003682
Code UNSPSC :
12352106
ID de substance PubChem :
24896429
Nomenclature NACRES :
NA.25

Source biologique

bovine bile
synthetic

Niveau de qualité

200

Pureté

≥95%

Poids mol.

376.57 g/mol

Pf

183-188 °C (lit.)

Groupe fonctionnel

carboxylic acid

Conditions d'expédition

ambient

Température de stockage

room temp

Chaîne SMILES 

[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

Clé InChI

SMEROWZSTRWXGI-HVATVPOCSA-N

Informations sur le gène

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

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Description générale

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.

Actions biochimiques/physiologiques

Bile Acid

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (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

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
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.
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
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